how to run a tiny business that isn’t an iceberg of dysfunction

It’s the Thursday “ask the readers” question. A reader writes:

I was really interested by the recent discussion in the comments on your post about the small business owner who gave his “best bud” as a reference, and how very small businesses can be Icebergs of Dysfunction.

It would be amazing to have more of an open discussion with other readers about what it’s like to work in a small business like that. I’m a solo business owner myself and would like to hire someone next year. I’m reasonably self-aware and an avid blog-reader of yours, so I hope I’ll be okay at it! But I’m curious to know how I can make sure to come across as sane, responsible, and financially stable during the hiring process. I’d hate to think I was losing potentially awesome employees because of something I was accidentally putting out there.

Readers, have at it!

{ 382 comments… read them below }

  1. Alton Brown's Evil Twin*

    No surprises!

    It’s a small business, you only have a few employees, and eventually they’ll know everything about the business. You should be upfront and candid about the state of the finances.

    When I was hired to run a small business, and I eventually got a handle on the finances (one of the owners was a CPA who did the bookkeeping), I learned that the owners had been highly leveraged when they purchased it. They evaluated me based not on a regular EBITDA calculation, but also on whether there was sufficient cash flow to cover the loan. I didn’t have anything to do with their decision to buy a small business with basically 0% cash down, but I sure as heck was blamed when we couldn’t cover the loan payments, rent, and payroll during the depths of the 2008-2010 recession and they needed a capital call.

    1. TypityTypeType*

      Yes, yes, yes. I worked for a one-person business for several years, and a big part of the reason it went well was that the owner was 100 percent open about everything related to the business — what money was coming in, which bills had to be paid first, the state of our relationships with vendors, etc. Even when things were tight or something went wrong, there were no secrets or surprises — so I never had to wonder or speculate on what might be happening.

      It wasn’t a perfect experience by any stretch — we were very different kinds of people, which sometimes caused some conflict (she is the only boss I have ever yelled at) — but on the whole it was a pretty good job.

      So LW, if you can resist any temptation you may have to be secretive or territorial about your business, that will be a huge help in making this work. As AB’s Evil Twin says, in a two-person shop, your employee will know all your business’ business soon enough anyway, so you might as well put it all out there to begin with.

      (But keep your personal business out of the office as much as you can — one of the reasons I ultimately left that job was that my boss’s fiance retired and started hanging around, and we couldn’t stand one another.)

  2. Nora*

    Very interested to see the responses to this one, because I grew up in a family business and it was more like the Titanic than an iceberg.

      1. Nora*

        The Titanic is the business, the tip of the iceberg is what they think running a business is like, the rest of the iceberg is what running a business is actually like.

          1. Roy G. Biv*

            I want someone to write a “running a small business book” using the Titanic and iceberg quote above as the basis for the knowledge.

            It has been my experience that small businesses tend to be run by The Talent OR The Head for Business, but not both, because each thinks the other does know know what they are talking about. And if The Talent hires someone to be The Head for Business, it is even worse, because, “Business Head, you just don’t understand about Talent.” “Well, Talent, this isn’t rocket science. All well-run businesses track expenses, employ accounting principles, fire employees who cost us business, etc.” And lather, rinse, repeat.

  3. voyager1*

    I think in the hiring process, explaining what he duties for the employee are is critical. You need to know what you want them to do however BEFORE you hire them. If you are coming at this thinking you need an assistant to do things as they come up…. you are setting yourself up for disaster because there will be no clear duties, expectations or boundaries.

    1. voyager1*

      Oh one other thing. We all have stories about small business disasters, but that you are asking why they become disasters I think shows some serious self reflection on your part. You are admitting you don’t know what you don’t know. I think that bodes well for you, that you are that self aware.

    2. irene adler*

      And the list of duties the employee will be assigned will grow longer and longer as each new situation pops up down the line. Some of that is expected; but be careful not to make the employee the “go-to” for all. At some point they will be overloaded. Try not to let that happen.

      1. Krabby*

        For this, I recommend creating a very thorough job description for anyone you hire and actively update it every 3-6 months (literally set a calendar reminder and review it with them). The thing about small businesses is that everyone wears a lot of hats and you just keep putting them on your head. Good employees will do it without you even noticing because they’ll proactively take things on.

        Keep track of those hats and then compare them every year. Make sure that you are compensating for big changes and are keeping an eye on how long the list gets.

        1. irene adler*

          And at this regular review (excellent idea BTW, Krabby!), might “check-in” that the employee isn’t feeling burned out juggling it all. Just compensation is great, but so is work/life balance.

        2. ChachkisGalore*

          Oh I think this is great! Another benefit – if you have an employee who has been with you for several years, picked up more and more responsibility along the way, but then leaves – you can refer to old versions and you have a timeline for what/how much is reasonable for the new replacement to be taking on at what points. I think this can be a bit harder to judge in a super tiny/sole owner company because its not something will happen regularly. Its so easy to fell into the mindset of “well Joe was doing a, b, c, d and e” so why can’t Linda handle all of that” – when Joe only started doing a, b and c and then after years of experience with the business or with you, did he start doing d and e.

          1. Quickbeam*

            Job descriptions and functional flow of work. My father had his own business in the 60’s and 70’s. He had an assistant he was extremely dependent upon to run the office while he did sales. She was amazing. And then she died suddenly. The whole family had to work evenings and weekends for 2 years to piece things back together since there was no continuity plan.

            1. Derjungerludendorff*

              Wow, that is a nightmare scenario in so many different ways.
              I’m glad they eventually managed to get everything back on track, but that must’ve been a really rough time.

        3. NW Mossy*

          And along with that, look at the list of duties for things that can be deprioritized or even dropped completely because they no longer align with what the business needs. Think of it like maintaining a garden – you have to weed and trim to foster growth.

          1. AllTheNope*

            “Maintaining a garden” reminded me of one thing I hated about working for small businesses. If work is slow, don’t assume employees would rather literally maintain a garden than miss a few hours. Even when I’ve been strapped for cash there are times when I would much rather go home early than weed the company flower beds, no matter how well-meant the busy-work opportunity.

        4. aebhel*

          This is really good advice. I think where a lot of small businesses falter (other than ego or disorganization) is in just not realizing how much work an employee is taking on and that it may be time to hire someone else–especially since a lot of the time business owners are living and breathing the business in a way that employees really can’t be expected to do.

      2. Kate, short for Bob*

        Add to this, if your business is growing you actively DON’T want one person wearing too many hats, because that can limit your growth potential.
        I was that person back in the 90s, doing everything from setting up computers to translating insurance text into plain English, overseeing problem clients, product design and marketing… It was crazy.

        And I knew – but couldn’t get my boss to believe – that I was turning into a real bottleneck. Because he couldn’t see the need for more people because I was doing those jobs – but he was also planning around my availability when he should have been planning around what the business COULD do.

        In the end I had to quit. And 2 months later he came round – with a cash bonus – and apologised. Said he’d had to hire 3 people and an outside consultancy to replace me, and now he got it.

        Company is still doing well – 10 times the size from when I was there, and I often wish I could have stayed (or that I had shares!). But it wasn’t going to work.

        1. AllTheNope*

          The flip side is when that ‘one’ person is the bottleneck. Don’t let one person wear all the hats if that person creates problems by refusing to share the hat or is a ‘legacy employee’ stuck in past iterations of the business and resentful of any change.

          1. Krabby*

            Yep, I’ve seen this happen too. In fact, in my current company, payroll used to be one guy like that. He had been with the company since day one and did everything on spreadsheets. He refused to automate anything or hire anyone, even as the company grew to over 500 people in four different countries. He was finally ousted and we hired two people to replace him, plus an automation expert for the whole department. It’s been three months and we’ve already found 8 processes where he was cutting corners to get things done, which could have cost us legal fees 10x his salary if someone else had been the one to catch them.

            1. Marie*

              I sincerely hope these cut corners did not result in employee being underpaid, and that if it did, those workers are appropriately compensated.

    3. lemon*

      Well, I think if someone needs an assistant, then they should *hire* an assistant. The problem is when someone hires for one role, like business coordinator, and then suddenly turns *that* role into a personal assistant job. Be honest (with yourself and candidates) about what your hiring needs are.

    4. SomebodyElse*

      Disclaimer: I have no small business ownership or employment experience

      I agree with this. It seems that where a lot of small businesses go awry is when they don’t have clear expectations. Now I’m not saying that a 3 person outfit needs to be run like a megacorp. But I think that some of the basic principles can be applied.

      Job descriptions: Even if you’re hiring an assistant or people who will wear different hats, I think it’s important to categorize the tasks they are doing. So that it becomes apparent when you need to expand and hire a second person. Let’s say Jane is hired as an assistant, but over time you grow and her duties turn out to be 50% shipping and receiving, 30% admin, and 20% bookkeeping.

      If you aren’t really tracking the day to day you wouldn’t know this breakdown. You then go to hire John because Jane is overloaded, what position do you hire John for? It would be odd to hire John to do the same work as Jane, so maybe you split out the duties and hire John for 80% shipping and receiving and free up Jane to take on a different ‘hat’ for the 50% or to increase the admin and bookkeeping %.

      Policies: Even if it’s you and 1 other person. For the love of pete… set some expectations and write them down. It doesn’t mean that you can’t be flexible, but it means your employee(s) know what the playing field is.

      Boundaries: Yes they won’t be as clear cut as in a larger business, but all the boundary rules apply. bosses are bosses and employees are employees. Stay in your lane.

      These are the big ones that I can think of off of the top of my head. I’m sure there are more though.

      1. Zephy*

        Cosign. I had a…not great experience as the sixth employee to be hired at a small business, because the owner didn’t really bother to define anyone’s roles. “Your job is to do what needs done, as it comes up.” That’s not a good way to run any kind of business, and it feels very bait-and-switchy from the employee’s side. I was clear about wanting an admin/front desk role specifically, which I got to do for about twelve minutes before I got tossed into the same duty rotation as everyone else.

        It also seems obvious, but the owner I worked for apparently didn’t realize, so: if you’re in an area or an industry that has a definite Busy Season and Slow Season, look at your finances through a full cycle of those seasons to make sure that you can actually afford to both hire and keep an employee. I was hired on with a 39 hour/week schedule. I never managed to actually work a full 39 hours in a week, and what hours I did have were cut back week by week until finally the owner told me business was too slow and he couldn’t afford to pay me anymore, because he hired me at the start of the slow season.

        1. Startup entrepreneur*

          not a good way to run any kind of business, and it feels very bait-and-switchy from the employee’s side.

          That is not the way startups work, though. You need to be flexible. That includes the founder.

          1. J.B.*

            I’m not sure I’d generally call startups functional though. And I have my doubts that male employees at startups are expected to pitch in on emotional labor.

          2. Who Plays Backgammon?*

            Flexible is one thing. Being misled about the job duties is something else. And if the job will require that kind of flexibility, employer needs to be aware of it and to communicate it clearly to applicants. While plenty of people enjoy constantly switching hats, some don’t. A job that’s a grab bag of whatever comes along at any minute sounds like a workplace definition of chaos. And an employer who doesn’t know what the job is that they’re hiring for isn’t likely to get what they want either.

    5. Pay No Attention To The Man Behind The Curtain*

      I was going to say something similar. It’s really common in small businesses to want every employee to be committed to doing whatever needs to be done in order for the business to succeed, but most people want to be hired for a specific job with predictable hours and boundaries between personal and professional lives — if the business isn’t viable without a specific employee, it’s just not viable period.

      1. Sleepy*

        I agree that even in small businesses, there do need to be strong boundaries for employees and predictable hours (or maybe especially in small businesses), but small business employees generally *do* need to be available to take on a variety of tasks. When you only have one, two, or three employees, you are simply not going to be able to have each person stick only to their job specialty and expect the business to run. Yes, there should be a core job description and tasks, but if the website is down, someone will have to get on the phone with technical support, even if they aren’t a tech person; if a customer is having a major problem with a service or good, whoever is working then may need to care for that relationship even if they aren’t a customer service specialist. Etc.

        1. Pay No Attention To The Man Behind The Curtain*

          That’s the way to lose good skilled employees though. If I’m hired to be a graphic designer, I’m not going to be happy mopping the break room, packing and shipping orders, or making sales calls…ever. If that becomes part of my “other duties as assigned” I’m going to be looking to leave. It’s better for the small business owner to understand that. If they want to retain good, skilled employees, they need to figure out how to run their business without putting undue and unwanted burdens on them. Either the business owner does those tasks themselves, or they contract with someone to do that on an as-needed basis if there isn’t enough work to make it full-time.

          1. AcademiaNut*

            The last sentence is the key point. If you need a skilled professional (like a graphic designer) for ten hours of work a week, then hiring a graphic designer full time and assigning them 30 hours a week of random work is going to make for a very unhappy designer. On the other side, hiring someone for random office work and making 25% of that graphic design tends to produce terrible design, because it’s a trained skill that not everyone can do well, even if you give them a Photoshop subscription. So contracting out (or buying packaged templates) is the logical choice.

            There are lot of people who quite like wildly varied jobs where they do a bit of everything and learn new stuff on the fly (although it’s sitll important to keep the amount of work reasonable). But it should be clear that you’re hiring for a multiple-hats, new duties as they come up job, so people who want to do 40 hours a week of predictable work can select out.

      2. aebhel*

        Yeah, employees are not generally going to be as invested in the success of a business as owners (for obvious reasons), and expecting them to be is a good way to generate resentment for everyone involved.

        1. Startup entrepreneur*

          I am extremely surprised that no one has mentioned the most obvious point: you need to grant employees equity in the business.

          Perhaps this might be less necessary for low skilled employees at small businesses that are likely to stay small (nail salons, etc.) but even there I think some formal profit- sharing plan is a good idea.

          1. Derjungerludendorff*

            I don’t think you NEED to do this, but it depends on what the owner expects from the employees.

            If they want the employees to be heavily invested and dedicated to the company, or if they expect them to make personal sacrifices for the company, or to serve as the backbone for the early years to fulfill the long-term growth plans, then yes. Giving them an actual stake in the company is probably a good idea.

            If they just want someone to do a certain set of duties, but keep it within reasonable hours/workload/dedication, then just regular salary and benefits will probably do fine.

      3. Startup entrepreneur*

        It’s really common in small businesses to want every employee to be committed to doing whatever needs to be done in order for the business to succeed, but most people want to be hired for a specific job with predictable hours and boundaries between personal and professional lives

        Sorry, but those people shouldn’t look for jobs at new companies. Defined roles at seed/early stage startups is just not in the nature of the beast.

        Not every job needs to be equally appealing to everyone.

        1. Clewgarnet*

          A small business isn’t necessarily a new business. I’ve just employed a plumber whose business has been going for sixty-plus years. He has one apprentice (his son), one additional plumber if desperately necessary (his father, who started the business), and somebody to answer phones/run his diary/do bookkeeping/wear every other hat necessary.

    6. What's with Today, today?*

      Yes. My boss is not good at this. Our Sports Director doubles as the Operations Manager (mostly paperwork), but he never says this during interviews, so every time we have a new Sports Director (three in my 15 years) they are surprised to find out they have to do the operations paperwork too and surprise(!) Sportscasters don’t typically love doing tehnical paperwork…

      1. What's with Today, today?*

        *Operations Manager is definitely not even a part-time position, it’s like three mandatory daily forms*

    7. Mama Bear*

      Agreed. And don’t make it a body in a seat situation or you’ll have a lot of turnover and it’s bad for morale, especially on a small team. Also be upfront about how startup-y you are because not everyone is good working at a start up, especially if they have built a career in many layers of management corporations. I also agree with hiring for the role, not adding roles to the person. If you have one person trying to be your CFO, your FSO, your office manager, and your hiring manager…well, that’s kind of a mess. I left a job where everyone not specifically a programmer had multiple hats (but didn’t always get paid for all those hats) and they tried to give my entire job to someone who was already juggling furiously. It was kind of crazy.

      Even though you are small and flexible, try to do things like regular reviews so those things are already in place as you grow.

    8. Leela*

      Yes oh my goodness, please have very clear expectations not only so you know what this person is doing but so they’re not spending days, weeks, or months panicking that they have no idea what they’re supposed to be doing and you don’t either so you might just let them go any time! I worked at a very small business where we had a program that tracked our tasks, and for two months mine was the vaguest, one-word term for things (think along the lines of being told to do “admin” instead of actually having the admin tasks you needed, and then having your manager get visibly frustrated with you when you asked for more details).

      If you can’t think of anything for them to do, TELL THEM and allow them downtime to do what makes sense for them if you still want them in for all their hours. You’re not wasting any more money on me if I go to pluralsight or kahn academy to learn job-related things than you are if I sit there wringing my hands while refreshing my inbox desperately hoping something will be in there so I’m not just staring forward for 8 hours, and I definitely won’t feel like I’m allowed to go to pluralsight or khan academy or whatever if you haven’t explicitly stated it. It’s very, very draining to just be kept “at the ready” when you don’t feel like you can do anything to keep yourself engaged.

    9. Turquoisecow*

      Oh god yes. My husband works for a small startup that’s growing and the CEO is constantly wanting to hire people because he likes them, but can’t articulate what he actually wants them to do. He’s still in small-business mode and wants everyone to be able to pitch in with everything, but at some point that becomes literally impossible. If you want to hire a guy to manage the alpacas, don’t ask him if he’s got experience with teapot painting!

      1. Startup entrepreneur*

        That is because startups often get judged on the quality of their team more than the substance of their business plan. Many investors are very clear on this point.

        1. Derjungerludendorff*

          Good point. But the quality of a team presumably includes what those people are actually capable of for your company.
          If you’re a custom-designed table business, and you decide to hire an agrarian expert, then that’s going to raise eyebrows instead of opinions.

  4. Black Targaryen*

    As someone who’s worked for a variety of dysfunctional small businesses, the key thing is to be transparent and honest about the functions of the role and team! The first few hires tend to have positions that evolve heavily. A gripe of mine is that I’ve been hired to do one thing, it changes dramatically/has tons more responsibility (which I like!) but there’s no acknowledgement/title change/compensation adjustment. Also, be mindful that no one will care about your business as much as you. Don’t expect your workers to approach things with the life/death decision making mentality that you do.

    Also—for the love of all that is good, hire HR!

      1. Elizabeth*

        And if your business is too small to support a full time HR employee, you can hire an HR firm to cover your HR functions for you.

        That’s what my employer does – we have only 40 employees, so instead of a dedicated HR person, we have a “fractional” HR person – she owns her own HR firm and acts as our HR person. I’m sure she acts as HR for a number of other small businesses as well – which makes it more affordable for small businesses!

        1. Jamie*

          I once worked at a company that outsourced HR to a reputable firm and it was a great solution. I don’t think enough people know this is a thing.

          1. The IT Plebe*

            Definitely! I just learned about that today, through Elizabeth’s comment!
            I hope more people know/learn about this. I cringe every time I read a letter that says “we don’t have an HR department.”

          2. Alli525*

            Yes! My former employer outsourced HR to a major national firm for things like payroll and healthcare, and our COO/CFO acted as the in-person HR person (e.g. the head of sales was notorious for scanning female employees head-to-toe, and telling the CFO helped matters tremendously). The company also saved a LOT of money on insurance overhead because the HR company could negotiate huge discounts because it was such a large company, vs our 50-person firm.

        2. Jdc*

          Oh yes do this. We did and it was the best decision. They were always a quick phone call away and only charged about $120 a month at the time. Of course they were going to charge us $5000 for an employee handbook so i did that myself.

          1. TardyTardis*

            This reminds me of The Warrior’s Apprentice when Miles Vorkosigan took over a space mercenary detachment, and they kept asking him about the pension plan…and he did the manual himself in a very short time, with some chemical assistance.

    1. Lucky black cat*

      “ Also, be mindful that no one will care about your business as much as you. Don’t expect your workers to approach things with the life/death decision making mentality that you do.”

      Yes – this. And I’ll expand by saying that this is fine and good.

      1. Elizabeth*

        Absolutely! It’s not your employees’ job to sacrifice their well being for the good of the company. It’s their job to take care of themselves first and foremost, and to perform their jobs satisfactorily in exchange for their paycheck.

        Small businesses that have a “we’re a faaaamily” culture are problematic precisely because they demand a degree of loyalty and self-sacrifice that isn’t appropriate given the nature of the employee-employee relationship.

        As a small business owner, you probably care a ton about the business and you would make personal sacrifices to help it succeed, and that’s great! It’s also important to protect your employees from any pressure for them to do the same.

        1. Jamie*

          I have found this to be the case in family business, even when they aren’t small. It why I have a deep bias against family run businesses now, despite knowing that some must be well run. Somewhere.

          1. Derjungerludendorff*

            It’s statistically impossible that every single family business is badly run.
            I’m sure they’re just really well camouflaged or something. Maybe they have secret meetings where all applicants are sworn to secrecy so nobody will know about their healthy work-life balance?

      2. Leela*

        Yes, yes yes! They simply don’t have the same stake in it that you don’t, and they won’t get the same rewards of the company doing well at personal cost to them

    2. lemon*

      I think being aware of position evolution is a really good point, and can move in both directions. Watch out for employees taking on bigger duties, of course. But also make sure that after you get up and running, you don’t expect the entrepreneurial employee that helped you get there to suddenly be comfortable doing more routine, administrative work. Speaking from experience of working with small businesses myself– I was hired to help get things up and running, but after a couple of years, after all the groundwork had been laid, they really just needed someone to do data entry and customer service, which is a completely different job that appeals to a completely different personality/skill set.

      1. Elizabeth*

        So true! “Start-up” mode and “maintenance” mode can be really different in terms of environment, culture, and job responsibilities.

        Personally, I thrive in start-up type environments and find maintenance type environments rather stifling. I like to bring order from chaos and solve complex, systemic problems – when everything is humming along like a well oiled machine, it’s time for me to ride off into the sunset to find my next problem-solving adventure.

        On the other hand, some folks do NOT like or thrive in a start-up environment but are absolutely stellar once things are humming along more consistently. And some people are hybrids and can do both well.

        So, know which kind of employee you need to hire, and be cognizant of how your business’s environment and needs change over time.

        1. FunctionallyDysfunctional*

          That is me too – I am so bored when things become well run. I need problems to solve!

        2. AllTheNope*

          Be able to recognize that up & running may look differently than you first imagined, especially if you have a proficient employee in start-up mode. I once reorganized the department I managed to be much more efficient in everything from inventory to production scheduling to employee satisfaction, only to be told (as I was handed my severance check) that the owners actually preferred the chaos.

        3. Startup entrepreneur*

          +1 for Elizabeth. I hate defined roles. This is why serial entrepreneurs move on after a certain point (for me, it’s when your selecting a corporate health insurance plan)

    3. Rugby*

      Agree about HR. There are actually consulting firms that specialize in providing HR services to small businesses. They can help write policies, make sure you’re complying with labor laws and help administer benefits. These are fantastic services for business that can’t afford to hire a full time HR person.

    4. irene adler*

      Yes – HR- is necessary.

      Just having an “open door” for all employees doesn’t equate to having HR. One can contract for HR services (compensation administration, hiring, etc.). Don’t need to hire a full-time HR person.

      We have the “open door” here and it’s useless. No HR. So your issues may or may not be addressed. Depends upon the cost and if your issue is with their “favorite”.

      1. Mama Bear*

        I used to work for a company that used a third-party HR company and shared that “back end” with some similar businesses. It actually worked really well.

    5. T3k*

      This! One job I panicked and took was for a small family owned business to do something like teapot design, but within a 4 month period it went from 85% teapot design and 15% customer service to 50/50 between the two. I despise answering phones, greeting customers, etc. unless I know from the start that’d be a portion of my job. I’ve had jobs since then where I did help customers as my core duties BUT it was clear form the start it was a major function of those jobs so I didn’t bristle at it.

    6. SDSmith82*

      And by hire HR- they don’t mean hire a consultant that’s too wrapped up in her own head to realize she shouldn’t leave the book showing everyone’s salary wide open and unattended in the break room while she spends 2 hours chit chatting about random things to the boss.

      That was my cue to leave that sinking ship. Boss sold 1 1/2 years after I left, and my position was eliminated by the new buyers.

    7. PNW Jenn*

      Eons ago I worked for a growing family business. They were a family in that I was their first hire who wasn’t married/related to or sleeping with someone else.

      It was a disaster. I lasted 14 months.

      Some obvious things:
      1. Avoid favoritism. Be honest with yourself about playing favorites.
      2. Don’t crap where you eat: avoid mixing family with business, and if you can’t avoid it, set (and follow) clear expectations.
      3. Hire an HR firm and use them. I was laid off from a small nonprofit some time ago and their neglect of their own HR policies cost them a pretty penny for my severance. When I worked for the family business, I felt I had no recourse when it came to HR and law violations I was experiencing.
      4. Related to this, hire experts you trust… and then trust them. Whether it’s graphic design, HR, or accounting, let this people be the subject matter experts. You can’t do and be everything.

    8. baffledmouse*

      Definitely this. I recently started work at a very small nonprofit (under 10 employees) and I just had a candid conversation with a departing employee who has been here years. She started as an assistant, they heaped on more responsibilities and programs for her that she has entirely managed on her own, without additional direction… but only gave her one title change/proper raise in 6 years. They wouldn’t promote her to the next level up because she doesn’t have a Master’s, which they’re saying is required… even though we’re doing the responsibilities of the higher title regardless. (To add to this, a staffer several years younger and with equivalently less experience – they both started at this organization straight out of college and the younger staffer took over the assistant position when the other was promoted – was offered the higher title because she recently finished a Master’s.) The lack of adequate compensation and recognition for the amount of work we’re doing is pretty concerning to me, and I don’t expect to be here long at all.

    9. Dust Bunny*

      This. My uncle owns an old and established but still small business and has complained for decades that he trains people . . . who then leave for bigger companies. Because he doesn’t pay them enough for their experience! He thinks they’ll stick around just because he gave them a start, even though his wages and benefits are behind the ball, and then get mad that they’re “disloyal” and leave for someplace that can pay them what they’re worth.

  5. Amber Rose*

    The obvious: your staff are not your family. Keep some professional distance.

    The less obvious, but helpful: Have a written dress code, code of conduct and set of rules. Having stuff in writing gives it both an air of legitimacy, and also gives off the impression that you’re prepared, which hopefully you would be if you took the time to write everything down.

    The bad idea that is (I hear) quite common: don’t tie your personal finances up in your business finances. In Old Job, the family finances were so entangled with the business that they had to hire someone to figure out the books when the owner died. What they needed was to bring on a partner, and they couldn’t because they couldn’t or wouldn’t untangle the books. It was a nightmare for me and the office manager every time we needed to buy anything. It was also a nightmare every time the owner’s wife who was also our accountant decided to go shopping.

    1. Mystery Bookworm*

      Writing out a code of conduct allows you to calmly think through things that otherwise you might be dealing with on the fly — which means you’re more likely to come up with good processes. A lot of things can slip through the cracks if you’re playing everything by ear and just troubleshooting as you go.

    2. Kiwiii*

      Seconding the written dress code and code of conduct. I recently joined one of the tech teams at a pretty casual nonprofit that doesn’t have a dress code (I asked the HR manager about it who said “we don’t have one, just look at what i’m wearing” of her tee shirt, jeans, and sneakers outfit) but have no idea what expectations are around, say, fun colored hair, ripped clothing, or piercings. The company is great, but I have some anxiety around unclear expectations and don’t feel like i’ve been here long enough to ask if it’d be cool to dye my hair purple like i’ve been wanting to lol

      1. Amber Rose*

        It me. I was so nervous asking if I could have purple hair (I could, and it looked amazing lol). We have a pretty comprehensive dress code but it’s from a safety standpoint rather than a professional one. So it addresses that you have to have long, unripped pants, but doesn’t really say if you can have rainbow hair or band shirts.

      2. Mama Bear*

        Yes, even if it is very basic have some kind of employee manual around insurance, PTO, leave requests, attire, hours, flex time/telework, holidays….If you can get away with casual, specify when you can’t.

      3. Startup entrepreneur*

        Just because you have anxiety about what to wear does not mean all employees want one. Use some common sense. I would never want to work/found a startup with a dress code. Part of the secret sauce in Silicon Valley and Austin and Tel Aviv is our informality.

        1. Cog in the Machine*

          If you can have a dress code without it being too strict it shouldn’t be too much of an issue, depending on your business. I got curious after starting to read AAM, and looked mine up. It’s two paragraphs long, and boils down to “wear clothing appropriate to your work site.” There are a few ‘do nots’, but they’re pretty much limited to ripped clothing and clothing with advertising, politics, drugs, or obscenity. I work for the government though, so YMMV depending on the business as to if that sort of thing is acceptable.

        2. Lisa*

          Startup Entrepreneur- Formalized dress code doesn’t mean formal dress. It can be very reassuring to those who want to have purple hair like the examples above, to have a documented dress code that explicitly has no hair color restrictions. And even in the most casual environments, eventually there is going to be that person who wants to exploit “no dress code” to wear something that makes coworkers downright uncomfortable. If dress codes are your hill to die on… good luck.

          1. Cog in the Machine*

            Yes, this. Even if it’s having to sit that one person down and saying that “no dress code” doesn’t really mean you can wear adult-sized footie pyjamas.

    3. Fae Kamen*

      YES. I worked at a small business owned by a man that shared a bookkeeper with another small business owned by the man’s wife. The bookkeeper also handled both of their personal finances. They were constantly moving money around, plus we were incorporated 10 different ways. The bookkeeper had been there 30+ years and they were in complete denial that she would ever retire. When she finally did, I heard it was impossible to find a replacement who could understand the extremely idiosyncratic system they had devised, let alone untangle everything (if they even wanted to.) They went through four bookkeepers in half as many years, getting incensed when each of them couldn’t live up to the original, and multiple times they brought her out of retirement. Whew!

      1. TardyTardis*

        That reminds me of the audit I once did of a small family business (“No, you cannot deduct vet expenses! You don’t use dogs in the business!” “And…here’s how to keep track of those expenses that you can’t deduct, you put them in THIS column!” We won’t even talk about the logging company that put their long term loans in the assets in their ‘balance sheet’…).

    4. EPLawyer*

      I cannot say this enough. It is NOT a family.

      Also, although you care very very very much about the success of your business, your employees are there to do good work and collect a paycheck. Do not expect loyalty, or that they are as committed to the business as you are. They are not. It’s not their business.

      Basically, treat it as you would if you were a manager in a large business. You would not expect your reports in Conglomerates R Us, Inc. to sacrifice for the business, never leave and accept lower than industry standard pay. Don’t do this in a small business.

    5. The Man, Becky Lynch*

      Co-mingling funds is extremely risky.

      That’s not “your” money, it’s the businesses money.

      Separate Business from Personal, money and personally. Save yourself the tax headaches if you’re audited as well. Nice way to get yourself some hefty penalties when they find out that you’re writing off personal expenses “accidentally”.

    6. High Score!*

      Speaking of, do not hire friends and family. Hold yourself to the same standards that large companies do. Every time I’ve been in toxic-ville, it’s been bc friends and family work together.

      1. Amber Rose*

        Eh, I’m mixed on that. I don’t really think anyone should hire their own friends or family. But most of my coworkers at this job are related to each other in some way and we haven’t had any issues with it.

      2. Cog in the Machine*

        Very very much this! It’s a whole lot easier to have a disciplinary talk with someone you aren’t related to or sleeping with. I get the “small businesses need all the help they can get thing,” but there is so much that can go wrong when your only employees are literally family.

      3. ZucchiniBikini*

        I am a micro-business (mostly operating as a sole trading freelancer) who uses subcontractors periodically. My three subbies are a former colleague with whom I’m on warm but professional terms; my best friend; and my eldest daughter. I realise that on paper that looks at least 2/3 dire, but in reality, it’s worked extremely well for me for the past 4 years. It probably helps that only around 15% of my overall workload goes to subbies, and they never work on the same things or in each other’s presence (it’s all home-based work).

    7. Zona the Great*

      Yes indeed. Separate Separate Separate! I worked for a single dad who owned a B&B and he convinced me to clean his home too. Never ever ever get that intimate with a boss. It blurred lines and I felt I couldn’t’ back out of the housecleaning because he was my boss.

      1. Jamie*

        I worked for a larger family business where the cleaning staff cleaned the owners’ homes.

        That was how she found out which sales rep was having an affair with the owners’ father.

        (lesson learned – don’t sleep in the day the cleaning staff is scheduled to come.)

      2. The Man, Becky Lynch*

        Ah I’ve seen this happen…only it wasn’t an employee doing the housecleaning. It was an employees spouse…

        It was extra dramatic when the employee got on the bosses bad side but he liked how his spouse cleaned their home…lots of discussion about if he could get away with firing employee and keeping the housekeeping services. Yuck.

        Other bosses have commissioned employees to do side projects for them but it was always because the employees were asking for OT and there was no OT/extra work at the shop available. I cringed when it happened and thankfully nothing bad happened [bunch of old timers who weren’t ever interested in a different arrangement but that’s the laborer life in a lot of ways].

    8. Malter Witty*

      Nothing like being told you can’t do something business related because of cost, and then finding out that the boss was going on a trip where they were expensing 5 star accommodations and meals.

      1. VeryAnon*

        Yes. “You can’t have the miserable raise I promised because the business can’t afford it. Also, enjoy looking after the business for two weeks while I go on a transatlantic vacation.”

      2. TardyTardis*

        “Oh, I can’t afford any raises, admire my fabulous car I paid cash for!”–my husband ran into that at an after school job.

  6. EveryDayIsARugbyDay*

    Have policies and plans written down and FOLLOW them! Improvising might’ve worked when it was just you but once other people are factors its going to cause trouble.

    1. Jedi Squirrel*

      Came here to say this. Document your processes, procedures, policies, work instructions, job descriptions—EVERYTHING!

      Have a procedure in place for making sure people are trained to follow them, and have another procedure in place for changing them if necessary. (I.e., change notices/change orders.)

      More businesses are sunk just because everybody has their own way of doing things. I worked in a deli once and was trained to make sandwiches four different ways—once by the owner, once by his brother, once by his brother, and once by his daughter. Of course, that gives employees carte blanche to make sandwiches their own way. Work things out ahead of time. If it’s a new issue/situation, sit down as a team and say “Okay team, here’s what we need to deliver. How are we going to do this?” and then take notes and work out a procedure right then and there. If it works, great. If you need to tweak it along the way (probable), get consensus on the best way to do that and write it down.

      Google “process turtles”. These are invaluable in my line of work.

    2. EPLawyer*

      If you have trouble drafting your employee manual/procedures manual whatever you want to call it, there are employment law attorneys who can help you do it right. The fee you pay them now will save you in the long run. Especially if you FOLLOW what you wrote.

      After you are running your business with employees it’s too late to start documenting. If you have been running without documenting, start now. Whatever you can capture, do so. It’s better than nothing.

  7. Tuckerman*

    I worked for a small business owner (diner) who regularly lied and expected us to lie to customers about the food, saying it was all made from scratch. I hated lying to our loyal customers. She never explicitly said how she justified it, but I’ve talked to small business owners who think they’re justified in lying, or paying poorly, not paying taxes, because they can never compete with the big corporations.

    1. earl grey aficionado*

      I worked for a small family owned restaurant that was very conspiracy/government’s-out-to-get-us minded and had a similar experience to Tuckerman. OP, you sound like a thoughtful person and I doubt this applies to you, but just in case: scrupulous ethics are so important to making a small business a pleasant work environment. A small business’s employees have their hands in everything which means it’s especially bad/stressful for them if crooked stuff is happening. They’ll be right in the thick of it. (Related: small business owners who loudly complain about taxes are generally inserting an uncomfortable amount of politics into the workplace!)

      1. Gazebo Slayer*

        An enormous yes to all of this. My mostly nonpaying crappy boss constantly blathered about how he was progressive and sticking it to the man and “making a living, not a killing” because he was running a small business, not one of the big bad soulless corporations or whatever. (He was also a conspiracy theorist, being an Alex Jones fan ahead of his time and a 9/11 truther.) He paid numerous workers less than minimum wage, and it was hard to get him to actually pay at all.

  8. Shark Whisperer*

    I work for a tiny organization (6 full time, 2 part time staff). I think there are two big things that help keep the dysfunction down.
    1. Every staff member has very clear goals of what they need to accomplish each month/quarter/year and how those goals fit into the larger organization goals
    2. We have individual monthly budget check-ins with the CEO. To explain further, my check-in will be with me, the CEO, and my boss. We go over all the outgoing and incoming expenses from the last month that affect my work and then talk about what we anticipate the incoming and outgoing expenses to be the next month. Most of the time these meeting are pretty short, but it definitely helps keep open communication about finances. At the end of the fiscal year, we also have a special meeting with the entire staff where we go over the whole past year’s budget, the coming year'[s budget, and the 3-year budget goals.

  9. beentheredonethat*

    In hiring and in running your business – for God’s sake, maintain proper boundaries. Don’t treat your employee like your slave, child, intern, nanny, wife/husband/bf/gf, or even your “apprentice.” If the hours are going to be odd, at least make them odd in a predictable way. Don’t lie on the high side about the hours per week you can offer. (No, don’t say “up to 20 hours per week” when you really mean “up to 20 hours per week once my business is established and successful, but really 3 hours per week right now, all on crazy different days.” Don’t offer any benefits that you aren’t prepared to give to them right away. Don’t have present the attitude that you’re doing the employee a favor by allowing them to work/slave for peanuts at all/random hours on your personal dream project which will someday rival the Apple empire, etc. Don’t expect the employee to be Everything You’re Not (organized, friendly, super-competent, psychic, etc) unless you’re paying them $100 an hour. Don’t interview them in your home.

    1. Kiwiii*

      Yes, clear working hours as as important for someone you’d like to hire for 4 hrs/week as they are for someone you’d like to hire for 40. Possibly more important, as it’s likely they’ll be arranging other jobs/responsibilities around your 4 hrs. And if they’ll be needed at the last minute or outside of working hours, be as up front as you can about that.

    2. NotAPirate*

      Especially this! Be honest on the hours and expectations. If you’re not sure try and figure it out or be upfront that you are not sure. There are plenty of great people out there wanting weird small hour side jobs. They will enjoy them. If you lie about 20 hours a week and then offer 10 you are going to have serious retention issues. I’ve also seen it go the flip, happy in 10 hour/week side job and then boss wants 30 hours/week and it can’t work out. Be clear. Talk to employees about changes in hours. Hire additional people if needed. Small businesses rely so much on word of mouth when starting, and that starts with your employees.

    3. Mama Bear*

      And don’t hire someone for x hours until you can pay them appropriately for those hours. Not saying you would, but underpaying someone is a recipe for turnover.

      1. Jamie*

        Or asking them to wait for their money. Payroll is a sacred trust and I don’t care if you have to sell everything you own…once payroll hours are accrued you pay them in full and on time…no exceptions.

        1. Kitrona*

          And keep money in the payroll account. I once got my (handwritten!) check and went to cash it, and there wasn’t enough money in the account to cover it. I was LIVID.

    4. Junior Dev*

      worst experience I’ve seen of this was a friend who was ostensibly hired to replace the role the ex-husband had had in the company…but kind of ended up being a replacement husband.

      Not in a sex/romance way, but his boss would ask him to do random errands at all hours of the day and night that were totally inappropriate for any employee, but especially someone who was a skilled analyst making $50/hr. And also to pick up the slack for things she had failed to plan for that became an emergency by virtue of waiting too long to deal with.

      I think this is where the “family business” dysfunction happens…turns out a lot of families are also very dysfunctional, but people get away with treating their spouse or child a way that is clearly inappropriate for an employee.

    5. AllTheNope*

      Don’t advertise a flexible schedule when what you mean is you won’t fire someone for taking an hour off here & there for a dentist appointment or school play.

  10. KEM*

    My experience as an assistant for a one-woman company was eh. It wasn’t the worst because she compensated me very fairly. As a part-timer in college, I made $20/hr which was much higher than what any of my peers were making at their part-time jobs. However, since she was a busy CEO, she seemed to expect me to be available whenever it was that she had the downtime to talk to me about things. This involved many calls before 7am and after 10pm, all unplanned. If we’d talked about this kind of thing beforehand, I could’ve been on board, but she just kind of expected me to be on-call 24/7 for whenever she was free. It ended up being bad because of that. (I also worked remotely, which didn’t help.) She would also ask me to do things that weren’t necessarily tasks I was comfortable with: looking up healthcare plans for her friend, ghost writing articles on how to get funding for businesses (when I was a sophomore in college and she was a 20+ year entrepreneur), ghost writing her email including correspondence to clients and friends without them knowing it wasn’t actually her responding, etc. So, I just think it’s important to have clear boundaries from the start. Of course things can change over time, but definitely have a clear job description from the start. And compensate fairly.

    1. cmcinnyc*

      “but she just kind of expected me to be on-call 24/7 for whenever she was free.”

      THIS was my biggest problem when freelancing for tiny businesses. There was a very common mindset that since I was freelance, that meant “whenever” and also meant instant access/response. The other effect of this was that sometimes I’d be called in to do something quite specific or asked for a particular deliverable, but other times–too many times–the owner just needed to “bounce things off” me or shoot the shit or whatever. Yes, I was getting paid but it was so draining. I think this one’s a big pitfall for people who started their businesses as side hustles, talking about it with their spouse while they cook dinner, outlining a business plan on the sidelines of kiddo’s soccer games, etc. They bring that same style into a employer/employee relationship and it erodes boundaries.

    2. mf*

      Yes, I think this lack of boundaries can also stem from the fact that small business owners often see their business as their whole life. Which is fine but your employees won’t feel the same way–to them, it’s just a job. So it’s not reasonable for them to demonstrate the same die-hard dedication to the business that you (the business owner) will.

  11. Anonymous for this*

    I’ve worked primarily at very small businesses throughout my working tenure, from a husband and wife owned print shop to a small company that has waxed and waned in size (but always small) over the past decade and was recently acquired by a much larger company. Sure, there were varying degrees of dysfunction but nothing egregious. So far, the only time I’ve heard the “we’re family” schtick is with the new parent company which threw a party for all the employees who had babies recently. (they are very into babies).
    Frankly, I think this forum (and the solutions offered) skews toward people working at larger companies.
    Be flexible, be kind, be professional. Don’t take things personally.

    1. smallbusinessowner*

      I have to agree with you. Every time I read about ‘red flags’ around small businesses, I think “how in the hell are small businesses supposed to get big, then?”

      1. AnonEMoose*

        I think this is a good point. I, personally, haven’t cared for the experience the times I’ve worked for smaller businesses. Mostly because, both times I’ve done that, I’ve been the person who got landed with a lot of unpleasant tasks because there wasn’t anyone else to do them.

        Also, I found the interpersonal politics were…not good for me. I do better in a larger company with more defined responsibilities.

        I don’t think there’s anything wrong with either approach (that is, enjoying wearing the multiple hats and learn new skills that can come with working for a small business, or preferring the more defined responsibilities and such of a larger company). I think it can be largely a matter of personal style.

        For me, I think the two points I’d reiterate for small business owners is the advice to keep professional boundaries, and to consult with professionals like HR when creating policies. And if you’re the business owner, don’t expect your employees to be as deeply invested as you are. It’s fine to have high expectations, but recognize that your employees have lives outside of the company, and this is a good thing.

        1. Jessen*

          I’ll be honest, while I’ve never worked for a small business, the idea of having a bunch of different hats and getting to figure out what needs to happen now sounds pretty awesome. Right now in government work my role is super incredibly defined and I kind of hate it. I suspect I’d be very happy in a small business environment.

          1. Western Rover*

            I’ve spent half my career working at small businesses that had just been acquired by large corporations, moving on after the acquisition gets either fully absorbed or is jettisoned. For me it’s the best of both worlds, “having a bunch of different hats” while enjoying the kind of health insurance and other benefits only large corporations can afford. Mostly it’s been accidental rather than planned that way.

          2. Allypopx*

            There’s a lot of ground between government bureaucracy and a mom and pop shop! If you actually were looking for a change I’m not sure I’d go that drastic.

      2. MsSolo*

        Not every small business wants to be big, of course,, but for those that do, they need to behave from day dot like the big company they want to become: keeping professional standards, maintaining boundaries between roles, providing appropriate accommodations and support for staff, and always keeping the business money separate from personal money. If they don’t, the transition is going to be rocky, and could tank the company anyway.

    2. Desperately seeking cute kitty*

      Yeah, I was the first employee at a startup that has now grown to 7 employees and it’s been great. So take the feedback that people here are giving (as well as the general advice about management that Alison posts on here), but also know that it is absolutely possible to make a small company that isn’t dysfunctional.

    3. Mockingjay*

      I’ve worked at medium companies, megacorps, and a small disadvantaged business (ExToxicJob). Current Job is a 20-year small business which is gradually growing; we hover around 150 employees in several locations. It is the best job I have ever had, because the company does all the things readers here have mentioned: quarterly reviews of finances and goals, careful investment in employees (benefits and salaries), clear roles and expectations which are reviewed with each employee quarterly. My company makes smart decisions about its core business: they do a few things very well and have built a fantastic reputation for quality. They invest in support tools: our buildings aren’t the most glamorous, but we have the best IT infrastructure I have ever used, way better than the megacorps. They also put a lot of money into skills training.

      As a startup, OP won’t be able to offer all this, but you do need long-term planning. Where do you want to be in 10 years? How large do you want to get, or do you want to stay small? How much profit do you need to reinvest in the business to stay viable and retain good employee(s)?

    4. Oranges*

      I think it’s the fact that small businesses are usually newer and don’t have a large population so can go toxic quickly. Also, a portion of small business owners are in it because they don’t work well with others.

      Large businesses have usually been around awhile so they’re the “success” stories where the toxicity didn’t kill the business.

    5. Leela*

      Wow I bet the party for any employees who had babies recently was a real treat for anyone who desperately wants one but can’t have one or god forbid, lost one.

    6. Startup entrepreneur*

      “Frankly, I think this forum (and the solutions offered) skews toward people working at larger companies”

      Naw, really?

      1. Anonymous for this*

        Haha! Right? Not every problem can be solved by transferring to a new team or taking FMLA. Especially if those options don’t exist.

  12. Raine*

    Second the hire HR comment. I’m a career admin assistant and I can’t begin to tell you how many times I’ve had to explain to someone that just advertising on Craigslist doesn’t mean you comply with fair hiring practices. There are companies who will do HR consulting for you.

    Also: write down what you expect your new employee to do. People who love uncertainty are rare. Define your expectations before you hire and get the list checked for sanity by a third party (here’s where your HR consultant can come in!).

  13. Four lights*

    Re: not being family. Under good circumstances a small business will feel a little like family, you can’t help it because of how small it is. but don’t mistake a good closeness that develops for actually being family. You don’t have to be standoffish, but you shouldn’t take advantage of people by thinking oh they’re a nice person, or their family. It’s still a professional relationship, however cordial it is.

    1. irene adler*

      Just remember, there is the chance you’ll have to lay one of these “family members” off at some point. It makes it harder if the lines between employee and friend are not crossed.

    2. PNW Jenn*

      When I worked for a small company, the co-owner’s brother (who also worked there) had a near fatal heart attack. This was a man who made 6 figures in early 2000s. The owners passed the collection plate with the expectation that everyone pay in. They didn’t have healthcare. Imagine that.

      A month later, my mom suffered a heart attack. I left work an hour early to get to the hospital, and was an hour late the next morning after having visited her in the ICU. They threatened to dock my pay for the 2 hours, despite my being salaried. They decided against it “out of the goodness of their hearts”. My mom survived.

      That was the day I started taking my desk contents home a little at a time so that I could walk out the door when the time came, which it did 3 months later.

      If you can, offer healthcare or some kind of subsidy.

      Apply practices fairly to all employees.

      1. Gazebo Slayer*

        Holy hell. That is incredibly cruel and petty. I hope you left them at a really inconvenient time.

    3. aebhel*

      Yeah, this. You can have a really great, warm, friendly relationship with your employees, but for the love of all that is holy, maintain professional boundaries.

  14. Super Duper Anon*

    Plan ahead before hiring! Do you know what you want the new employee to do? Do you think you can reasonably fill 40 hours a week for that person with work? Can you, as a solo person used to handling everything, be comfortable providing your employee with autonomy without micromanaging or holding onto your former duties?

    1. LadyByTheLake*

      This! Before you hire do some real introspection about whether you are ready to let someone else be responsible for certain things or if you just want them to be an extension of you. The “extension of you” notion will never work.

    2. Elizabeth*

      Also – have you done the math to confirm that you can actually afford to hire them? Including payroll taxes, benefits, raises in the future, etc.

      It’s not ok to gamble with other people’s livelihood; If there’s legitimate uncertainty about your ability to afford them in the near future, let your job candidates know that so they can choose for themselves whether or not to accept that risk.

      1. Who Plays Backgammon?*

        Or start with a temp? Don’t mislead them about the prospects, just see how it goes, what you need, what you can afford?

        1. Gazebo Slayer*

          And DON’T say it’s temp to hire unless you really are pretty sure you’ll be able to hire them!

    3. Amy Sly*

      Can you, as a solo person used to handling everything, be comfortable providing your employee with autonomy without micromanaging or holding onto your former duties?

      Lord, this. First job after law school was with a solo who would rewrite everything I submitted “his way.” Okay, fine, I’m learning … but then the next time I submitted a version that included sections written “his way,” he’d rewrite it again!

      If there’s a way that things have to be done, write out the instructions to be clear as crystal and then let the new hire do it that way.

    4. aebhel*

      Oof, yeah, the micromanaging. My spouse just left his job of 10 years at a small business and there were a lot of reasons but one big one was that his boss couldn’t stop micromanaging even once the company got way too big for everything to go through him; he expected his employees to read his mind and wouldn’t give them the autonomy to do their jobs properly.

  15. CaliCali*

    As someone who worked for a small business that was on the cusp of being functional, but ultimately was that proverbial iceberg, here’s my advice:

    – Create a warm, inviting atmosphere with lots of camaraderie! That’s a great thing! When it’s small, you need to get along and you’ll naturally get close. BUT
    – Hire people who are right for the job you need, not because they seem like they’d be a good buddy. As you grow, you need competency and accountability, not more friends. Along those lines…
    – Recognize that people will grow and move on, and do not take their resignations personally.
    – Create processes, but sensical ones. They don’t to be bureaucratic nightmares — keep em lean — but you gotta get things out of your head and onto paper. You can change these processes as necessary, but at least have a baseline.
    – Don’t nickel-and-dime. Give people the tools they need. Let them pick reasonable hotels. Let them order their favorite pens. These things make a difference.
    – To the extent possible, offer flexibility. When I’ve done the large business/small business calculus, the large businesses tend to offer me more in terms of career growth path, resume building, and benefits. But small businesses have given me more flexibility, a refreshingly faster pace, and more connection to the future of the company.

    1. WellRed*

      So agree with small companies offering a faster pace. Nothing like death by committee to kill any enthusiasm for getting something done.

    2. Krabby*

      “– Recognize that people will grow and move on, and do not take their resignations personally.”

      This! Create an environment where long notice periods are rewarded and treated respectfully. If you show your employees that, they will be more inclined to tell you in advance when they are planning to leave. When you only have 1-2 employees at a time, that can be a life saver.

      1. Bigglesworth*

        I agree. I currently work at a small law firm. There are three people total – my boss, his associate, and me. I had to tender my resignation recently because of a family matter that means I’ll be travel long out of state more (my dad has a terminal illness). Although my boss was understanding when I submitted my resignation, he began to take it personally this week and is making me fight for things that I didn’t like I would have to (like the fact that my law school gives credit for my work – apparently it’s not fair to my boss that I’m leaving before the end of the semester since my dad is dying and can still get credit for working here). I may have recommended this firm to other law students with the caveat that you need to have a thick skin to work here, but him taking my resignation so personally and responding in such a petty manner has burned all bridges with him for me.

        1. Coffee*

          Ah yes, cunning of you to get “easy credit” by having a Dad with a terminal illness. I’m sure everyone will be exploiting this loophole before we know it. /s

          My sympathies to you and your family. My Dad died in my final year of uni and I felt weird about asking for help from my uni but in hindsight I did need it. Your boss is wrong.

    3. Mama Bear*

      Also, don’t make people guess. If you need to replace someone, shuffle the team, etc. have a formal meeting about it. I didn’t need to know why my manager was permanently replaced but I needed the official word that they were replaced! Not saying it directly/not being upfront with issues that affect employees leaves people hurt and frustrated.

      1. Archaeopteryx*

        Yes, this too! If you promote someone, make it very, formally clear to everyone. And don’t hold anyone accountable for your staff’s performance if you’re unwilling to fire people. And….. don’t be unwilling to fire people!

        Some people- harassers, lazy people, people too toxic to make it in a healthy environment- seem to tool around looking for a cozy setup with little oversight and no stomach to fire them, and then nestle in forever, driving out good staff. Don’t be that habitat for them.

    4. Archaeopteryx*

      All this- also, check people’s references! Do it for real, not just as a gesture. Really investigate the people you’re bringing in.

  16. What's with Today, today?*

    Let me preface this by saying I LOVE my job at a small family business, my workplace and my bosses. I’ve been here 15 years and I’ll never leave. But it can be a little nuts. I’ll try to think of things through the day that are odd and reply to this comment, but this is one of the quirkier ones.

    We get paid on the 1st and 15th. Boss refuses to get direct deposit, and if the 1st or 15th fall on a weekend or holiday, we get paid on the first business day back to work. So let’s say New Year’s Day (payday) is on a Friday…we’d get paid on Monday the 4th. It’s never negatively affected me due to my husband’s job, but it really hard on some of my co-workers.

    1. Amber Rose*

      Is that not illegal where you are? :O
      It’s incredibly illegal where I am. You have to get paid on or before the agreed on date.

        1. Natalie*

          I believe this is usually governed by state & local law, I don’t think FLSA mandates specific pay check timelines anywhere.

          As long as you were paid at least monthly, and you were informed of the particular way they handled Sundays/holidays at the start of employment, this would be legal in my state.

      1. What's with Today, today?*

        No. Our policy actually specifically states that payday is the 1st or 15th, unless they fall on a weekend or holiday and then you will get paid on the first business day back at work. You know going in it’s the policy, it just sucks.

        1. Rugby*

          Just because it’s policy, doesn’t mean it’s legal. Most states have laws around how often employees must be paid. It’s probably worth looking into that for your state.

          1. What's with Today, today?*

            I didn’t want to expand further, but we’re in Texas. A co-worker looked into it and my husband is an attorney whose asked an employment lawyer friend. Because it is specifically spelled out in the policy, it’s legal.

          2. Mimi Me*

            Just because it’s policy, doesn’t mean it’s legal.
            ^^^^I want to stitch this on a pillow!^^^^
            My husband works for a small-ish business as a driver. They recently had a larger company buy out the smaller business. The new company instituted a policy that all employees had to take lunch breaks. Nobody communicated this to the drivers who had not been taking lunches as it extended their day and instead just eating their stuff while driving. They always got paid for their hours worked with no issue. The new company started clocking the drivers out for 30 minutes every day whether or not they stopped for lunch. I was the one who discovered that this was happening as my husbands paystubs didn’t match the hours we recorded on our own. The company tried the whole “well our policy is….” BS but I wasn’t having any of it. The money out of 3 weeks worth of pay was equal to 2 weeks worth of groceries – it was not an insignificant amount. I did some research, printed off the federal law that says that employees need to be paid for all time worked, and handed it to my husband to give to the manager. Across the top I’d typed, COMPANY POLICY CANNOT OVERRIDE FEDERAL LAW. My husband, bless his heart, did argue the point with the new company and not only did he get the pay, but they amended the lunch policy for the drivers so that drivers get a 30 minute paid lunch for which they are encouraged (but not required) to stop and eat.

        2. Kiwiii*

          Ours is similar but it’s the 1st or 15th, unless they fall on a weekend or holiday, and then you get paid the closest business day BEFORE pay day. Which is the legal version of the policy your employer has.

          1. What's with Today, today?*

            It’s the most common method, yes. The best practice I think. But in my state, what he is doing isn’t illegal.

          2. londonedit*

            Being paid monthly is more usual in the UK, where I am, but it’s always been the case that when pay day is on a fixed date (say, the 25th or the last day of the month), if that day isn’t a working day then you’re paid on the closest day before that date. Currently we get paid on the last Thursday of the month, which avoids that dilemma but also means we sometimes have 4-week pay periods and sometimes 5-week ones. Also, the office is closed over Christmas, so we’re paid on the last working Thursday of December, which they spin as ‘Isn’t it great, we’re paying you early so you have money before Christmas’ but which actually meant, this year, ‘Oh crap there’s six full weeks between December’s pay day and the last Thursday in January’.

          3. emmelemm*

            Yeah, fortunately this is how my boss does it at his small business. It’s usually not an issue for me either way, but man, if it was, it would be a big issue!

    2. Rusty Shackelford*

      Mr. S worked for a small family business that decided to delay payday by several days because the person who did payroll (the daughter of the owner) went on vacation. They decided their employees had no reason to complain because “you were notified ahead of time.” Yeah, sure, that makes it okay.

  17. Carlottamousse*

    If you are a reasonable and sane person, that should come across in an interview with candidates — asking reasonable questions, listening to the candidates, and answering their questions, etc. I’ve worked for a functional and awesome small business that has had 4-8 employees varying over the last several years I’ve been here, and we’ve managed to stay pretty drama free. Communication is really important, and what helped me the most when I was first hired was the open door policy the two founders had (it was just the founders, an assistant and I) for any and all questions I had no matter how basic. What struck me the most in the hiring process was that they admitted what a big investment it was for them to hire me, which made me appreciate much more both the opportunity to work there and also that they valued the work I was doing and learning. I liked knowing they cared about my success at the company from day 1 and were putting effort into helping me make my position a success.

  18. Briar S*

    Oooh I just left working at a teeny business in large part because of the business owner so yes I have some opinions on what to do! Hopefully some of this is already known to you from being a reader of Ask A Manager, but here’s what I’ve learned from experience is important.

    1. Make sure you’re aware of the market rate for the job you’re hiring for, and provide appropriate financial incentives for people to work for you. And if you are unable to afford market rate, make sure you are clear to your employee that you will support them if/when they decide to move on to somewhere else, that you understand you cannot keep top employees forever if you can’t pay them at a reasonable rate–and then make sure you do succession planning so you’re prepared when they do leave!

    2. If you have not received any training in management, get some. Someone running their own tiny business may not have had the opportunity to learn what constitutes good management practices, and you may not even be aware of what your gaps in knowledge are. Having good intentions towards your employee is not enough.

    3. Try to provide a working environment where your employee feels like they are truly able to come to you with concerns they have, so that issues get dealt with in a productive manner.

    4. Be aware that even though you and your employee may spend a lot of time with each other, you are not best buds or family, there is a professional boundary between you. This means you shouldn’t overshare personal details with your employee and neither should you expect them to share personal details with you if they don’t want to. It also means that you shouldn’t expect/require personal loyalty from them to you or your company. To your employee this is their job, even if to you the business is your baby.

      1. Mama Bear*

        #2 – YES! And be willing to train your managers as you promote them if they need it. Too many small businesses give people teammates and then make them manage without any experience, training, or guidance. Don’t do this to your people.

    1. Manders*

      Yes to #1! So much small business dysfunction comes from either 1) making poor hiring choices because the owner refuses to pay market rate, or 2) making weird management decisions or withholding positive feedback because the owner’s afraid employees will leave if they believe they’re worth more.

      It was a very weird experience for me going from a small company that underpaid to one that paid well. A lot of the bizarre feedback I was getting from my old boss was actually her trying to convince me I wasn’t good enough to expect a raise! I’m glad I didn’t fall for that.

  19. Lady Catherine de Bourgh*

    Hire good people and then let them do their thing. My boss is convinced he’s an expert in everything, I think because he was doing so much on his own for so long, so although I am supposed to be doing high level strategy stuff, it ends up being “make sure the buttons on this email are the color I want them” and “we don’t need to collect data on our marketing efforts, I already know what customers want because I’ve been in the business for so long.”

    Don’t do that! There are so many talented people working on this team that don’t get to actually do what they do best because he only wants to do things his exact way. It’s created terrible morale and high turnover.

    1. Rayray*

      I’m currently going through a similar issue.

      One thing that happens at small businesses is that they don’t keep up with growth, so employees will Co stantly just get more and more added to their plate until it becomes unbearable and another person needs to be hired. Then, it’s an issue of what work to hand over to them. The first person has been doing the job for so long, they don’t want to hand things over fearing it will get done wrong or they don’t want to take the time to train. Hire before workloads become unmanageable. Also, cross train because someone will give two weeks notice and then it’s a mad scramble to figure out what to do with that work when the same sole person has done that job for the past five years.

      1. Lady Catherine de Bourgh*

        This is exactly the situation I’m in right now! Long-time employee finally got fed up and quit on the spot, and no one knows what to do with all her work (and there are several tasks that no one else even knew how to do, so it was a huge scramble to train ourselves to be able to pick it up quickly). AND boss went out of the country for three weeks a couple days later, so we were left in a major mess since he controls access to so many areas on our system and won’t give anyone else access for when he’s gone.

        If you have employees, you HAVE to learn to delegate. You cannot and should not try to do everything on your own or control everything your team is doing.

        1. rayray*

          I quit a job back in April, and I had been planning my exit for a long time. I mentioned to management a few times that I really thought we should cross train, because I was the only person doing certain tasks. Another person did similar tasks, and it would have been pretty easy to teach her the other things I was doing. Management was just like “Oh, yeah good idea. We’ll do that” Never happened. It’s too bad I couldn’t actually sit down with anyone and train them, explain the little hiccups that happen and what to do or who to contact. I wrote up very basic instructions to help, but it would have been easier if I could have actually sat down with someone to teach them. Not my problem, but I feel bad for whoever got stuck with the problems after I left.

  20. Natalie*

    I’m definitely biased because it’s a service I provide, but – have good professional consultants for things that are out of your area of expertise, especially once you have an employee. For taxes, bookkeeping, payroll, and HR there are a lot of out of box services through big companies like Quickbooks or through local CPA firms (whomever you engage for your taxes is a good place to start). An insurance broker can help you with workers comp and/or health insurance (these will be different brokers). Yep, it all costs money, but it’s the cheapest way to pay.

    There’s a lot to know, even with one employee, and frankly it’s a PAIN IN THE ASS with experience. Even with 1 employee and no benefits, in my city you have: overtime, minimum wage, sick & safe time, ACA notice, wage theft notice, completing an I9, new hire reporting to the state, written pay stubs, withholding and remitting state & fed taxes and filing returns, reports to Unemployment, reporting to and paying for workers comp, filing and distributing W2s, final paycheck, and possibly garnishments for debt or child support. You’re in business because you love making/selling/servicing widgets, not because you’re a payroll expert.

    Having an onboarding and employment process that is professional will give the impression that you are professional, compared to the employer that hand writes their pay stubs or whatever.

    1. Ann Furthermore*

      Yes to all of this. In college, I did bookkeeping for a small family owned business of about 30 employees, and did the payroll each week, using a pretty antiquated system that required a lot of manual work. I am an accountant, so I’m meticulous and detail-oriented by nature. And I’m telling you, it did not matter how careful I was, or how many times I checked and rechecked my work, I always made at least one mistake. When you’re dealing with the money that goes into people’s pockets, that’s a big deal.

      Everyone was pretty nice about it, even though I would be kicking myself. I’d cut a check to make up the difference and then record it on the following Monday. There was one guy, though, who was such a jerk. I had to garnish his wages for back child support, and I ended up withholding too much. He got his lawyer to call me and yell at me for “stealing” money from his client, and threatened to sue if I didn’t pay him what he was owed immediately. I had never done a garnishment before, and made a mistake in calculating what I had to withhold. It was a pretty simple fix. I was so ticked off though, that when the guy came back at the end of the day to pick up the check, I told him, “Here you go. You can use that $75 to help pay the $150 it probably cost you to sic your lawyer on me.”

  21. Rayray*

    Hire and promote employees based on merit and qualifications, not because it’s your cousin or the brother of another employee. If they’re truly the best one for the job, fine. But if it’s based *only* on them being a relative or a buddy, that’s nepotism and it isn’t all that fair. Now If it’s a simple job like a mail clerk, maybe it’s not so bad to help out a young cousin who needs a job while in school but you still need to hold him to the same standards as everyone else, he has to follow the same rules.

  22. The Dude*

    Not a small business, but in my last job interview, the interviewers were quite candid about the fact that they had been thinking a lot about professionalism and how they should best present themselves as an employer during an interview, that they were trying some new things, and that they would appreciate candid feedback about what was and wasn’t working in their interviewing style.

    Just saying out loud that you care about professionalism sends a strong signal that you care about professionalism!

    1. Penguin*

      Yes to this, although I would caution that “just saying out loud that you care about professionalism” absolutely must be backed up with actions. For example, interviewers asking for feedback is great, but unless they then incorporate that feedback into later actions and decisions, their words ring hollow.

      TLDR: don’t ever treat business decisions as superficial.

      1. The Dude*

        Fair enough! I guess I’ve been so deprived that the mere mention of caring about professionalism was a breath of fresh air! lolsob

  23. AVP*

    I think a would-be hiring manager in this situation also needs to think about managing and how that fits into the overall business structure. If you’ve started a business because you’re great at TASK-A, and now so many people want to hire you to do it that you need to hire a second person, that’s not a business.

    Having a plan for what your business does, how it should be structured, what growth looks like, what good and bad management looks like in this context, at least a vague outline of policies and HR…that’s a business, even with two people. Have one before you hire someone, and get coaching on managing and hiring if you don’t have experience in that area. You may be a great baker or filmmaker or marketing consultant, but that doesn’t make you a great CEO until you put in the work to get there. And it may be an investment that takes you away from other paid work…that’s ok. You will make more money off it in the long run than if you skip it.

    Also, +100 to the person above who said that transparency is key. If you have less than, say, 10 employees, everyone will know everything about the clients and finances so you may as well be upfront about them.

  24. Mystery Bookworm*

    Don’t expect that your intentions will directly translate into results. There’s a lot of advice here about setting boundaries and creating a healthy working dynamic. Few people, however, set out to create a business with unhealthy boundaries and a toxic work enviornment.

    Think critically about concrete steps (360 reviews, outsourcing tasks, rules regarding the management chain) that you can take to ensure an open, collaborative enviornment. Solicit lots of outside feedback on your ideas, and don’t be afraid to let that feedback marinate before you pass judgement on it.

    Just thinking: “It’ll be different with us” is not a viable strategy.

  25. Laura H.*

    Be honest.

    I work for a small, family-owned business that is sadly slow, but I’d much rather them say “traffic patterns at your usual shift times aren’t great/ in general traffic’s not great/ we overhired/ it’ll take some time to figure out the demand pattern as we are in our first year.” (All of which are true) Than to work and find out they can’t pay me.

    First one still sucks and is acknowledged as such, but their transparency and honesty is huge to me. (I do pop in every so often (once a month) to make a buy of their products (sometimes a gal needs homemade ice cream) and and remind em -reasonably- that I’m available.)

  26. blackcatlady*

    Keep careful financial records! You need to be able to show you’ve paid withholding (federal and state) Medicare, unemployment etc. Get legal advice on if you have to issue a W2 or 1099 – that differed with status of employment. Due diligence up front may be tedious but it will save trouble down the road. Since you are small you will probably use a third party service. I don’t know how you avoid something like the recent MyPayRollHR scandal! That burned thousands of small businesses.

    1. Natalie*

      I don’t know that there’s any way to avoid the possibility that you’ll get caught up in a massive fraud scheme! But I think you could reduce the risk by retaining control of your funds if you are using a small scale bookkeeper – that is, they do the calculations but you actually write the checks. Or chose a well established payroll firm.

      Maybe check into crime coverage for your business insurance? Although with just one employee it might be better to self-insure. That is, have enough in reserve to cover a duplicate paycheck.

    2. WellRed*

      I once couldn’t work for a day because the owner/manager “forgot” to pay quarterly taxes or some such and had to drive the check to the state capital (this was eons ago). That was nerve wracking.

    3. The Man, Becky Lynch*

      You can do payroll directly through Quickbooks if you use their software. It’s worth paying for the subscription and having everything calculated correctly. They will remit your taxes too if you pay for the services. I always used their services until we got big enough that ADP was a better choice.

      But always confirm that the government has gotten your money! ADP automatically takes our taxes out and remits it. I log into EFTPS to confirm they sent the funds, even though they’re a huge system, I trust…nobody. They screwed up royally when PFLMA reporting started *snarls*

  27. Mimi Me*

    Setting reasonable expectations for yourself is very important. A lot of small business owners have their whole lives wrapped up in their business and have this expectation that anyone who works there should feel the same way. That’s not reasonable at all.
    I once worked for a family that expected me to put my whole life on hold for the business because they were doing it. I was 100% present and into the position when I was scheduled to be there, but it quickly soured because I wasn’t coming in to help out on my time off or staying late when they decided to extend hours last minute. And the owner wanted me to give him 6 months notice when it was convenient for him – as in “Oh, I can’t accept your notice right now. I’m travelling for the next six weeks. We can talk about this when I get back and we can work out when you can give me this notice then.” It did not go well when I left.

    1. Turtlewings*

      “I can’t accept your notice right now” askldsajk then accept my total and immediate absence, my dude. You don’t actually get a vote in this. Sayonara.

  28. Brazilian Hobbit*

    Understand that your employees are working to make a living. While your company may be a passion project for you, it’s a way to make a living for them. That means you have to pay them fairly, on time and understand that this is their career, and that leaving on time, taking vacation, sick leave, or finding another job is not a personal betrayal.

    Don’t put all your eggs on one basket, or all your hopes/knowledge on one employee. Think that this employee can find another job, win the lottery or have to quit on the spot due to a family emergency and have a plan in place – having just one person know how to do everything is a terrible idea.

    1. Jules the 3rd*

      +1 : Be crystal clear to yourself that even if your business is your baby, it’s ok if it’s just someone else’s paycheck.

      And be honest with yourself about what you can afford – look at the cash flow data over history, not just projections.

  29. ElleKat*

    I’m employee 1 at such a small business, professional services similar to a law firm. It has been the toughest job I’ve ever had and I’m looking to get out ASAP. Boss and I previously worked together at a much larger firm, and we meshed well enough that they asked me to join at the solo venture. I asked about investing/partnering but I am junior to Boss, and they wanted to keep that going.

    At first all was ok as we scraped out some client work, working in coffee shops in the like. We would talk about how we were a team. I put in a huge number of hours, seven days a week, put my personal life on hold and made a lot of family sacrifices to get the business going. Our clients like me, some even prefer dealing with me. I did pretty much everything everything in those early days – firm admin, marketing (self-taught with website, Mailchimp), plus our actual work where I’m trying to grow my career. As we took on an intern and then an admin, I handled all the HR. Boss, to this day, expects me to be available 24/7, and I often respond to them on weekends, middle of the night, you name it. I admit I got a bit codependent and would do things for Boss just to “be a friend” or “be supportive,” and Boss agreed we should be “friends.”

    But, Boss never thought of me – it started small with Boss getting their own cubicle when we finally moved to a shared workspace, but not bothering getting one (or the accompanying bathroom pass) for me. When we started the business I assumed I would be involved in client meetings and pitches, Boss said I was “inserting myself” and overstepping despite the fact that I had often done all the prep work for these. Later on, Boss also told me I would never be allowed in such meetings and they “don’t understand why you want to make your living at something you’re so terrible at” because, despite my good relationships with clients and in our industry, they believe I can’t get along with people. At the same time Boss expected validation and emotional support from me at all times as they fretted about the business’ future, and would lash out when they felt I wasn’t giving it.

    Boss started blaming me for mistakes as me trying to hurt them or the business. They would make bizarre accusations like me trying to hurt the business. Boss also continues to severely reprimanded me for not being cheerful enough in small talk. I had a serious talk with them at that point about how I needed to be treated – they responded by posting a job for another support staffer (which they quickly took down) and saying we would no longer speak in person (of course eventually we had to). This sort of behavior has never really stopped and I’ve learned to just sort of get out of the way when it happens.

    Over a LONG time we reached a bit of a detente, as I realized I couldn’t get as emotionally or professionally invested in this person, and I was putting my heart and soul into a business that didn’t appreciate it. I still searched for ways to get Boss to support my career and growth, only to get vague reasons why they wouldn’t, such as I “lack presence.” Boss continues to acknowledge that I do excellent work and clients love me, but they are not interested in growing my career because, in their words, they believe I “don’t like” them.

    Then, Boss decided to take on a partner who they had never met before but “liked” (implication being – they don’t like me.) New person brought no experience in our industry or clients and is only a few years older than me, but was given the same rank as Boss and is paid significantly more than me — still no word on whether I can ever hope to be promoted to that level. Finally, recently Boss talked to an industry publication about this new partner, saying how happy they were he had joined because they’d realized they “couldn’t do all this by myself.” It was like the last two years, and all my work, never happened. I’ve decided the weekends/mornings I spend crying and feeling worthless were enough, and now I’m looking to get out.

    I’m trying to hold it together as I look for something else. I have a great rep in the industry and with our clients. But, the experience has shattered my confidence and I’m thinking of leaving the industry altogether.

    1. Supervising Librarian*

      Oh my. I totally identify with your experience. Thirty years ago, this was me. I left the industry and went adjacent. I did seek professional help to leave. Took a paycut/went to graduate school. The year I spent in that boundary-less environment stood me well in that I have very firm work/life boundaries and alarm bells go off when they are crossed. Good luck.

    2. WellRed*

      That’s how a lot of abuse works. Start out small, slowly ruin the victim’s self confidence, then punish them.

    3. The Man, Becky Lynch*

      Your boss groomed you to accept their bad behavior, it tends to always start out slow and in that kind of “forgetful” ways.

      I would bet you money that when you leave, your clients will follow you and tell you how much of a shitbag they think your boss to be.

      The problem here is that you spurred off with him, so he had you isolated and that’s how you start to groom a victim.

  30. Hiring Mgr*

    Haven’t read all of the comments but I’ve seen several mention having written policies, dress codes, etc. I might not go overboard on this – one reason people look to work at a small co rather than a large one is to get away from corporate type policies on these things. Sometimes “use good judgment” is perfectly fine.

    1. Rugby*

      When policies are done right, they are just good judgement written down. I don’t think its a good idea to discourage a small business from having written policies.

    2. Commuter*

      In my experience working for a small, family owned company, they used the lack of documentation to screw us over multiple times. Eventually they downloaded some other company’s handbook from the internet, didn’t even change the names, and even then they were constantly contradicting what they’d given us.

      I think the benefits of having things documented outweigh the risk, but it’s a fair point not to go overboard and be rigid. The documentation holds the business owners and the employees to clear standards.

    3. Taura*

      That seems really vague though? If it were me being hired at a small place, especially if I were the first/only other employee than the owner, I’d really appreciate at least something stating “Jeans are okay, as long as they aren’t ripped. Closed toe shoes you can walk in, etc” for a dress code and “Here’s how we want to handle x, y and z situations in general.” I feel like that would leave enough space for people to use their best judgement like you said, and also provide a starting place so people aren’t completely blindsided by anything that comes up.

    4. The Man, Becky Lynch*

      No. Legal wise, you want this in writing.

      You want to be able to have something to point to if someone shows up in something incredibly inappropriate.

      I would be careful about being strict in terms of don’t ask for formal dress when you’re operating a landscaping business! But to say things like “Casual attire is acceptable, no swimsuits or animal onsies though.”

      In reality you can write these to really read as “use your judgement” but at the same time protect yourself when someone decides their judgement says they can show up in their pajamas and shuffling around barefoot.

      You need policies in place so people understand what you expect.

      I say this as someone who is a small business professional and loath the idea of corporate type policies. There’s a huge difference the two.

  31. Nancy Drew*

    The biggest things for me now after working in a small, family business for over a year and a half:
    -Start with a written offer letter and company policies/holidays/etc. There were things agreed upon during the offer phase that have not come to fruition including raises and benefits. Because it’s a small business without formal procedures and this conversation was with the owner, I can’t really address this now because there’s no evidence.
    -Create a more formal feedback/review system. It doesn’t have to be handled the same way large companies do but creating that transparency with employees means a lot. We only had “reviews” last year because 3 new admins were taken on (myself included). The other few employees have been here close to a decade and we were the only ones reviewed (sat down and told we’re great). All of us received a generic letter IN THE MAIL detailing our feedback (vague praise) and salary/benefits changes (not cost of living or in line with the great feedback received).
    -Be transparent. We’ve been waiting on our 401k benefit for months now. The owners are in the process of moving the account and because of this, employees can’t contribute. We’ve been told frequently in this time period “paperwork is done” or “we’re getting portal access any day now.” Again, it’s been months and we would have rather heard “we’re still doing paperwork, we’re sorry this is taking so long”
    -Do not mix personal and professional finances. Your employees will be able to see this and most will feel weird about your country club membership, maids, car insurance being paid out of company funds. (From experience)
    -You are not a family. At the end of the day, employees will need to feel comfortable addressing concerns with you and you’ll need to feel comfortable with the fact that they may leave. Keep up boundaries. The (only) 3 women in the office are constantly being “fathered” by our co-owner brother bosses and it’s an uncomfortable position to be in. Treat your employees as if you had a very serious and large HR team to keep you accountable.

    1. Another HR manager*

      +1000 — that opening letter makes clear the agreed to rate of pay, any paid leave (know the laws for your state), if no paid leave indicate what is expected for taking unpaid leave. Make sure the letter does not over promise. This is a letter to set expectations on each side.

      And know yourself — will you err on the side of being too familiar? too harsh? too micromang-y? And then read up on how to counter this. Do your kids say things like “you always expect me to know this already!”. If so, up your training plan!

    2. Natalie*

      My state just passed a wage theft law that actually mandates a written notice of the various terms of employment. When they were first discussing it I didn’t anticipate that being part of the legislation but I’m glad it made it in there.

  32. AndersonDarling*

    This is a little tangential to the question, but I really feel that hiring right is the key to having a functional small business. And if you have the right people running a professional company, then your new hires won’t get the icky “Family business” vibe. These are the small business hiring mistakes I have witnessed:
    1. Owner hired their friends and relatives because they were, you know, perfect in every way. You’d think incompetent people would crash the company quickly, but they don’t. All they have to do is make the owner feel good and all is great in the world.
    2. Hiring people who weren’t 100% experienced in what they do. You need people who have been working in their industry and managed their part of the business. There isn’t anyone to train you. You can hire a great financial professional, but if they haven’t managed an entire financial arm of a company, then they only know how to do 50% of the job. And they won’t know what they don’t know. You have to be ready to spend the big $$ to hire pros into these key positions.
    3. You have to check references…even ones that are not on the reference list. You have fewer checks and balances in a small company and a fraudster only needs to get in the door and trick one or two people to get away with everything. These people target small businesses because they just need to charm the owner to get the job, and the owner won’t have the time/motivation to dig deep. I worked at a small business that hired MAJOR fraudsters again and again. Executives that have been fired for fraud or misconduct have no other options but to get under the radar jobs, like at small businesses. Be careful!

    1. irene adler*

      RE #1:

      if you do hire friends/family members, be open to listening to employees who might notice that your cool Uncle Joe, who’s been minding the books, hasn’t paid the payroll taxes in over 2 months. Don’t make it difficult for employees to approach you with issues like this. Otherwise, you’ll have employees leaving -without a real explanation. And a serious problem will continue.

    2. The Man, Becky Lynch*

      1. A way to think about this is also that you do NOT want to ever be surrounded by “yes!” people. You’re not a celebrity, you need people around you that are going to say “no” and in reality that’s them looking out for you and the business in most cases. You don’t want to always hear “yes” because if you only hear “Yes”, you think everything is going perfectly…until you start getting checks bouncing and OSHA knocking on your door or calls from other assorted agencies who are checking up on reports or just the random spot-checks they do.

      2. Seriously. It takes a long time to find people with expertise but it’s worth wading through months of resumes and interviews than hiring someone who isn’t experienced in the areas you are hiring for. And yes, they don’t work for free soda and “conditional bonuses” Be aware of what they’re worth, they sure know how much they’re worth.

      1. Gazebo Slayer*

        Even (especially?) if you ARE a celebrity, you don’t want to be surrounded by yes people all the time!

  33. The Man, Becky Lynch*

    Be easy to communicate with, in this kind of setup you want people to feel safe raising concerns or telling you ‘no’ at times. You want to also make sure you don’t pile everything on the back of one assistant, you need to sit down and have your procedure documents at least in a rough draft before you hire anyone. Don’t try to find someone who can sink or swim, we’re very few and far between and you will go through a ton of people before you find that “unicorn”.

    I would speak with a consultant to make sure your structure is fully in place and you’re aware of what it means to employ someone. Get an employee handbook put together before you hire your first employee. Know your benefits structure if you’re going to be able to offer them. Know that if you cannot offer benefits, you will have to pay much higher than whatever salary website you look at at any given time, if you want someone who is going to stick around. Seriously, assume you’ll have to pay someone more in the end because of the small business structure.

    Many small business owners have unrealistic expectations of their employees and that’s hard enough but if you’re paying dirt level wages, you are setting the stage for that toxicity to brew.

    Don’t be secretive. These people have to be trusted. Yes, they have to earn it in some way but in the end, don’t hire someone if you cannot trust someone. Be careful with letting any one person do your books and not keeping an eye on everything that’s going on. This means outside bookkeepers as well. Most small businesses I’ve dealt with have been embezzled from and you want to make sure transparency goes both directions.

    If you are betrayed by an employee at some point [read, stolen from] you have to learn from the situation but cannot let this cause you to not trust people. You have to figure out where you went wrong and correct yourself there [hint, you usually go wrong if you trust someone in the honeypot without any auditing on your side and you aren’t reading your bank/credit card statements every month to glance for things that look questionable.]

    Employees are not family. They are not your son or daughter or mother or father. They shouldn’t know every weird thing that goes on in your life. And you’re never entitled to knowing their personal life either. If theyr’e sick, they’re sick. Trust. Trust. Trust. Trust. Trust. Trust. Trust. Trust.

  34. pretzelgirl*

    Please, please know how to your employee’s job. I worked at a small business where the director had no idea what I did. I had no one to go to if I had a question about how to do something or even how a certain system worked. I was told to “Google it” so many times. I basically had to train myself, rely on the person who left before to come in on his off days to train me (and he was only there for 2 months). I went on maternity leave, and I begged my boss to get someone to cover my work. He refused. I had to work during my maternity leave, which didn’t work out very well because I had a colicky baby. It was hell. I had my baby in June, came back full time in September and I left the company in February and still hadn’t caught up with my work from being out on maternity leave. It was honestly the worse time in my life. I suffered a great deal of PPD/PPA.

    1. The Man, Becky Lynch*

      Well this can be kind of impossible in some ways, since some positions are created because the ownership has no idea how to do certain things.

      I come from this angle because 9 out of 10 of my last bosses didn’t know a darn thing about how accounting works, that’s why they hired someone to do it.

      HOWEVER! You need to have a backup plan! You need resources. I can call our CPA or the boss can call the CPA if a tax question pops up that we’ve never dealt with before or whatever.

      But seriously, don’t expect your assistant to also double as your bookkeeper, your IT person and your personal therapist, etc. You need to have them doing things that you know how to do and they are indeed assisting you with, to take it off your plate. If they do start doing something that you aren’t aware of how to do, have them teach you, have them write their own procedure about it.

      And I agree, don’t depend so heavily on someone that they cannot take time off. Really assume that they may be abducted by aliens as they walk to lunch one of these days. Have that plan in place. Without that plan, there is utter chaos and you risk way too much.

  35. Chili*

    Make sure you are actually paying at or above market-rate for the positions! And don’t try to pass off equity in the business as a replacement for compensation. Most start-ups and small businesses don’t make it to the big time. Give equity as a plus, if you can, but don’t try to make someone’s compensation mostly dependent on the company doing extremely well.

    1. The Man, Becky Lynch*

      Equity stakes also only make sense when you’re planning to expand to a huge setup. That’s the idea in tech and why tech startups love to throw that in there, their big plan is to be the next guy bought out by Microsoft or Google.

      I read a small business as something different. These are usually very slow and grow organically. Therefore never give equity because you want to be full owner, fully in control of your business. If you do sell in the end, you want all those profits for yourself, you put in all the sweat and tears and risks.

      Also never have a partner. If you can’t hack it as a single owner, your business is not ready to grow yet. Don’t sell off pieces of a pie before it’s even fully baked!

  36. Liane*

    Trying to remember how my dad ran his 1950s – early 80s painting and carpentry business (new & remodels, single family homes, apartments, hotels). I think his crew was 10-12 people max. I was in my teens when he retired from it, so didn’t know a lot of details but here’s what’s stuck with me.
    1. Be honest and trustworthy and hold your employees to the same standard. When my parents divorced and Dad got custody when I was about 11, he was able to leave jobsites and be there for me after school until I was older largely because he had a good crew with a foreman he was comfortable leaving in charge. Whatever pay arrangements he had with suppliers, he kept to, and like clockwork, he was at his bookkeepers’ at close of quarter to take care of taxes. (He did the day to day books–literal books!–but was smart enough to let a CPA handle the heavy lifting.)
    2. Take care of your employees, care about them, but you have to remember that might include letting them go if there are problems. I’ve wrote here before about how Dad had a couple of Vietnam vets on his crew that he eventually had to let go because of drug addictions. But he never forgot them and at least one visited us once or twice when he got back on his feet–and I know Dad would have rehired him if he’d had the work.
    3. Involve your family only to the extent they are capable and willing–better reasons than “they’re a relative.” I know my mom did a few things–phone answering, maybe buying materials or doing paychecks–before they divorced. I learned quickly how to take calls and messages at home and to add long columns of figures (with one of the earliest calculators). As a teen I sometimes helped him as a go-fer during school breaks, which I credit for my ability to spot quality work to this day.
    4) Part of caring for employees is good wages. Be generous with raises for good work. Dad once told me that he wouldn’t give a raise for less than $1/hour “because less would be insulting.” (I checked and $1 in 1975 equals just under $5 now and I think he paid $5 or 6/hour starting in the 70s)

    1. The Man, Becky Lynch*

      Yeah, my bosses never gave less than $1 raise either over the years for that similar thought process.

      My boss for many years also setup a profit sharing program as soon as he possibly could! One of my coworkers once asked him why he did that instead of keeping all the profits to himself.

      “Because this means the tax-man gets less, I’d rather YOU have it than the tax-man!” and also “because your work here is what keeps us thriving, this is my thank-you for helping keep us profitable and food on all of our tables.”

      [Bossman was a big ol’ hippie and the best ever, even when he was a grouchypants sometimes because hard work brings out some hard feels sometimes.]

    2. anon4this*

      For inflation, that’s $5 hourly in 1970 (assuming full-time) equal to $10,400 annually, or $33 hourly and $68,822 in 2019.
      So, either your dad was regularly paying blue collar work at more than double the minimum wage of that time (and more than enough for a family of 4 to live comfortably upper middle-class), all during recessions and the economic turmoil through the 1970s? And he made a profit? As a small employer?
      Given the economic upturn of the 1980s (thank Reagan for the deregulation), you’re dad would’ve made a killing as he paid more than reasonably for what’s seen as blue collar (and most employers take advantage and hire minorities at a much lower than average rate for painting and woodwork) and he was hiring Vets with some of the highest rates of PTSD ever (at the time) due to the Vietnam War. Unbelievable!

      1. The Man, Becky Lynch*

        High risk and skilled labor like carpentry, always came with a higher than regular premium for wages, if you wanted people who wouldn’t bounce for the first person that was willing to pay them a few cents more an hour.

        This is why my dad was able to comfortably support a family of 4, my mom was a stay at home mom until I was out of elementary school. If you didn’t get paid by the small guy shop, you’d join a bigger place and it was all unionized work.

        So there’s nothing shocking about the amount of money he was paying if he was a standup guy who was sharing the spoils with his crew.

      2. Gazebo Slayer*

        I don’t know where you live, but I wouldn’t call $68,822 upper middle class for a family of 4 in my (high cost of living) area.

  37. Miss May*

    IF you hire family, PLEASE treat them exactly like employees, and not family. My partner use to work for a small business, and half the staff was family. It was very hard to bring up issues because they would directly criticize the owners son. Your employees should feel free to bring issues to you.

    1. The Man, Becky Lynch*

      Also only hire family if you’re willing to fire them.

      You will be taken advantage of. The business owner in the family is always an easy target by those who are looking for coattails to ride. And then they are banking on that “Oh but Uncle Teddy…he’s Uncle Teddy…mama would be so mad if I fired Uncle Teddy…”

      Don’t set yourself up and risk everything you’ve built for Uncle Teddy.

    2. Mimi Me*

      My mother worked for a family owned business that worked well for this reason. Clients often didn’t have a clue that the staff they were interacting with were all related. My mother was hired when they started to grow the business and later they hired my sister. They wouldn’t let my sister call my mother “Mom” at the office and insisted that they use first names. Their own mother was one of the employees and they employed the same rule with her. They ended up selling their business to a larger organization and walking away wealthy and still liking one another, so they did that whole family thing well.

    3. Alexandra Lynch*

      I worked at a hotel where I got written up several times for adhering to the procedure the housekeeper taught me, and not being psychic to know that the Owner’s Mother had decided that things ought to be done another way, and she had showed up midway through my workday and redone everything.

  38. HarvestKaleSlaw*

    I think a key one is to remember that this is not your employee’s business. They are working for a paycheck. They have plenty of good reasons to want to see your business succeed – but they are not going to ever own a piece of it. They have lots of good reasons to fear your business failing – but they did not mortgage their home to get the seed money. It’s not their dream, or their identity, or their chance to be a millionaire. It’s a job.

    Small business owners can get very stressed about the success of their business, which is all or nothing for them. They are putting in 80 hour weeks, so they get angry when employees leave right at five and take breaks. They are sometimes not paying themselves to stay afloat, so they glare daggers at every penny spent on payroll.

    Sometimes owners get resentful and suspicious of their employees. They start nickle-and-diming them and monitoring them constantly and berating them for any mistakes. Sometimes owners cope by filling the business with people who, through their own issues or straight-up Stockholm Syndrome, care JUST AS MUCH AS FAMILY about the business. Since it is unhealthy and irrational to care that much about the wealth of an effective stranger, you wind up with a horrible sea of dysfunction.

    Anyway – ask me about the small businesses I’ve worked for!

  39. Alternative Person*

    People have already mentioned hiring out HR, but don’t discount hiring out other things as well, even if you take on another employee. Especially for tasks that are limited in scope, or require a certain amount of skill, look around for free-lancers or similar rather than adding to the plates of existing employees (at least until you reach the point where hiring another employee makes sense).

    Also, for the love of whatever you hold dear, talk to your employee(s). I worked for a while at a place where the other five people barely spoke to each other, let alone to me and I felt like I was sliding off a cliff because of the absence of adult conversation. People would shut down any line of conversation at the first opportunity, it was the weirdest thing.

    1. thatoneoverthere*

      Yes, please get to know your employees and hold conversations that aren’t work related! Don’t cross professional boundaries of course. But I am person with a family and a life before an employee. It’s nice to know you care about me as a human being as well as an employee!

  40. Adereterial*

    Don’t make up HR policies without understanding your legal obligations. Preferably your moral ones, too. You’re going to get it wrong, potentially very wrong, if you decide what YOU think is fair and reasonable doesn’t match with what the law requires. Ideally get it checked by a professional.

    Case in point – UK law allows employees to ‘self certify’ for the first 7 days of a sickness period that’s longer than 7 consecutive days (not working days). You don’t need a medical certificate, nor can your employer require one. I worked for a small (6 people) company, which had a policy that said you had to provide one for absences of ‘7 days or more’. They fired someone who refused to provide one for day 7 of a 7 day absence as his GP correctly refused unless a fee was paid (also perfectly legal). He took it to Tribunal for unfair dismissal and although they ended up settling out of court, the settlement wasn’t small. The HR policies were written by the part time admin assistant, and she ignored my attempts to advise her she was mistaken on a fair number of things. I’d say about 70% didn’t properly comply with the law and another 10% were outright illegal.

    1. Natalie*

      A couple of jobs ago I was working for a company of nearly 50 people that had a bunch of illegal policies written down in their employment manual (mostly relating to not paying people in various circumstances where they are required to be paid). It was astonishing. Like, in the 30 years or however long you’ve been operating you never had an attorney look this over?

  41. NotAPirate*

    Have a clear working space. Do not have the employee working out of your dining room. If you can’t afford to rent a room somewhere then clear a space and block your families access to it, like a garage or other room with it’s own door. Likewise for the love of all things, give them a bathroom. Do not tell them to go to McDonalds etc or share a bathroom with your kids. Do not work out of a coffee shop or a library. If you cannot afford work space you can’t afford an employee yet.

  42. Chaotic Neutral*

    Please for the love of God pay people on time. Getting my check late was something I experienced regularly working for small businesses and it was AWFUL.

  43. Reality Check*

    Two things I’ve noticed: being so loyal to someone Who Was There From Day One that once the business expands and more employees are hired, the owner turns a completely blind eye to WWTFDO’s faults. Meanwhile, WWTFDO is a tyrant over the others, rude to the clients stealing from the company, etc. Owner slowly allows this person to gain control….and employees are pissed.
    Along the same vein, and someone mentioned it above – hiring family members and treating them that way, especially if they are incompetent and/or being paid twice as much to do half the work as the rest of your staff. I’ve seen both of these things happen, and it bred HUGE resentment among staff.

    1. irene adler*

      Yep. Be open to listening when folks have screwed up the courage to tell you that a co-worker is not all you think they are.

  44. JKP*

    When I hired my first employee to work for me, I started with a temp agency. In the beginning, I didn’t need someone long term, just someone to get me caught up and then I would run out of work to give them. This gave me the great opportunity to try a lot of different people in the role, and also the option to not have them come back the next day if it wasn’t a fit. It also forced me to prepare great documentation so a new temp could show up and start working with minimal direction.

    When I eventually needed someone full time permanently, I had a much better grasp of what the job responsibilities would be, the skills I needed to look for, and the type of person who would succeed in the role. I had also gone through my own learning curve as a manager with all the temps, so I had already gotten past some of the micromanaging etc that I was prone to. The person I hired was great and worked for me for many years until I closed the business to relocate and open in a different area.

    I think that without the experience of all the different temps, I would have been setting myself to have that same temp experience but in slow-motion, hiring someone and taking time to figure out they weren’t a fit, then hiring someone else, and it would have taken much longer before I got the right person in the role and before I developed my own skills as a manager.

  45. SecondCoffee*

    I worked in a tiny headhunting firm once. My boss was the owner. My most immediate colleague was his daughter. His brother also worked for the company and occasionally his wife, other children, and their spouses made appearances for a few weeks when they were between jobs and needed income. The boss was a conservative, observant Catholic. I am a liberal Hindu. I lived with my then-boyfriend (now husband) at the time I worked there and we were not married. Every day I came in to work and my boss would ask if I was married yet. I would say no and he would tell me I was going to hell. I would reply that I was aware of that and then go about trying to make money for his business. Worst 18 months of my life. Ironically, I stayed in touch with his daughter and have been very important for her career development, as I am the only person she can ask for a reference because all her other colleagues were family.

  46. ArtK*

    Great advice here. I’m going to summarize some of this in a simple fashion:

    None of your employees will ever be as dedicated to the business as you are. Be honest with yourself about that before you hire someone. This business may be your life, but it’s simply a job to them. They will have different priorities and you will need to accept that.

  47. You can't fire me; I don't work in this van*

    Set expectations ahead of time regarding how your vacations will be handled. My friend worked as a server at a higher-end family restaurant. Once a year the family would close for a month to go back to the Old Country. She was never told that when she was hired, and they told her about the trip with only a few weeks notice so she has to scramble to find another restaurant to pick up shifts for that time.

  48. Quill*

    Know what you will need peripherially for your employees to do their jobs. See: a functioning subscription to an antivirus if they must use computers/the internet.

    Source: how I became tech support at a 5 person business despite knowing literally only 2 things about computers.

    Don’t branch out into products or procedures that your current workplace can’t actually physically support. As in: if you can’t safely dispose of biosamples, don’t use them, and if your sinks are run via sump pumps, they’re not proper laboratory plumbing.

    Source: same company, cleaning up the worst sump pump crisis to ever occur in an alleged biosample lab.

    For the love of god, write out your standard procedures as training materials for your new hires.

    Source: Same. Dang. Job.

    1. Amber Rose*

      Good point, and as an addendum to point 1: if you need your person who knows 2 things about computers to become IT, sign them up for some damn classes or buy them some books or something. Google is a shitty teacher in many ways. It’s also a time consuming, frustrating way to learn things because you have to sort through the useless stuff to find anything helpful.

      Source: Taking a job as a document controller and teaching myself to become marketing designer, web master, HR person and safety manager. After the management switch up I got permission to send myself to class and everything has been so much less stressful.

      1. Quill*

        I know exactly enough HTML to blog on LiveJournal and have removed a total of 2 viruses by hand. I can google whether a computer problem is a me problem or a find actual IT person problem.

  49. Quinalla*

    Based on my experience as an employee of a small business on things they did and did not get right:
    1. Have a code of conduct and vacation, sick, etc. policies in writing. It doesn’t have to be 100s of pages like a big corp, but have something people can refer to when inevitably people forget if we actually have the day after Thanksgiving as an official company holiday or not?
    2. Think about how you will handle things that maybe you aren’t required to do as a small company, but people are going to need: maternity leave, medical/family leave, etc.
    3. Do reviews, please! You can keep them low key, but do them. I had one review at my small company in my 13 year tenure and that was ridiculous. Sure, I got some random feedback here and there, but I had no way to effective improve, ask for raises, etc.
    4. To that point, make sure you are giving raises and keeping up with market rates. This is not just an issue with small companies, but I’ve seen it happen more there.
    5. As others have said, don’t treat it like a family, don’t take it personally when people move on, etc. Business is business. That isn’t to say you can’t have close relationships with people you work with, you probably will, but you have to keep a Boss first mentality and you can’t expect undying loyalty from your employees.

  50. Leela*

    I worked at a very small business where a husband/wife team were two extremely high positions that shouldn’t have cross-over, but definitely did (he, who was not in my department and had no oversight in my work, would show up in our one-on-ones. It really made it look like she wasn’t capable of having these meetings on her own and only go to be a manager because of the tiny company with a high-ranking member marrying her). There were also way less of us to push back as a group on something, even if it was all of us, and if one or two people weren’t comfortable pushing back (which is the case everywhere), that took a wrecking ball through our ability to approach management as a group so I’d be very receptive to feedback and VERY open to hearing what people tell you, and try not to think “well i’m not hearing this from everyone else!” and instead really look at things objectively.

    There were a lot of freedoms in such a small company which was great, but sometimes i was just dying for some overseer to come in and be like “wow, that is NOT how you a run a business” because it was far too easy for someone who was high ranking to have their whims just implemented.

    If you feel like your business is falling short, please please please don’t try to make it up with activities/things like that. Sprucing up the place, taking everyone on a dinner/paintball etc, won’t make up for low wages, lacking health care, terrible hours, or offset a really bad manager that you won’t remove. All it will do is make their job search period slightly more bearable!

  51. The Very Worst Wolf*

    Fun Topic! Here’s my two cents:

    Design your business as though you’ll employ hundreds one day – whether or not that’s the goal. By which I mean, build a business where no one (including yourself) isn’t replaceable. Document your processes; have systems in place; make goals and expectations clear; and don’t allow any single employee to become the lynchpin to your entire operation (and if someone is, set a plan to correct that over time). Build around the concept of scalability, where every decision doesn’t have to be made through you (even if currently that is the case).

    The biggest problems I see in small businesses is that a) the business owner is in charge of every single thing, even though they have some employees who could do more with the right systems in place; and b) the business gets held hostage to bad employees who for one reason or another, the business owner feels they can’t afford to hold accountable or potentially lose.

  52. Uhdrea*

    Be extremely clear with your own family about what employees are not there to do and then enforce those boundaries so your employee isn’t caught in the struggle of knowing something is outside their job, but feeling unable to push back.

  53. MaureenSmith*

    I’m running a small family business and I wish I’d found AAM earlier! It would have helped to avoid some very bad situations.

    I second all the comments about being honest about the job, expectations, hours, etc. Once hired, be open and available for discussion. We have weekly staff meetings & regular quality, R&D, etc meetings with the entire staff. No one is excluded from helping the business to succeed.

    Keep boundaries between your personal and professional life. Especially finances, the now-retired former business head mixed them and left me a huge mess. Be friendly with your employees, but not friends outside of work. You still have to impose discipline and be prepared to fire them if needed. You can’t be perceived as having favourites, which results in a lot of grumbling and discontent. The same applies to hiring any relatives in the future, they have to meet expectations or be gone. Boundaries are also not having employees do personal chores, not expecting responses when they are off the clock, etc.

    Supporting employees keeps them happy and engaged. Paying a decent salary is a good start. Having flexible hours helps. Allowing employees to manage their time. Encourage learning and engagement in whatever industry. Let them take ownership of projects that encourage their personal growth.

  54. Snow globe*

    My husband has worked for a number of very small start-ups, including one where he was the only employee. I could write a book on all the things NOT to do, but will summarize a few things that I wish his employers would have done.
    – Make sure to pay, on time, with appropriate deductions for taxes. Have W-2’s ready by the end of January. Hire an outside company to handle if necessary. If employees are non-exempt, understand and follow overtime rules.
    – Even if your clients are late paying you, you still need to pay employees on time. That includes expense reimbursement.
    – If you are not naturally an organized person, strongly consider hiring an office manager. One of my husband’s employers went out of business because the owner never got around to sending out invoices to clients-even though he had a huge backlog of receivables.
    – If you are closing for holidays, pay your staff.

      1. Snow globe*

        Yep, some owners just thought if they weren’t being paid the staff didn’t need to be paid. This has been an issue with multiple companies.

        1. Gazebo Slayer*

          Ooh, the conspiracy theorist I mentioned working for upthread accepted a project, had me do it, and then told me AFTER I had finished that I wouldn’t be paid for it because it was a “favor for a friend.”

          Do not ever volunteer your workers pro bono.

  55. Lauren*

    Br open about finances. Go full disclosure on them if you are under 5 people. All of these below show structure.

    – This business is an LLC, and completely separate financially from own finances.
    – We have a health plan of X and it costs $ per month for employees.
    – Vacation is Y. Maternity leave is Z and paid / unpaid.
    – I’m a methodical person, and give examples.
    – The person who takes this role will be successful if …
    – This is a business, we are family-owned, but its a business first.
    – Pay them market rate.
    – Tell them that title promotions include – JOB, Senior JOB, JOB Manager, Associate Director of JOB, Director of JOB – even if the number of people in the company does not increase – responsibility increases would with each promotion. Sometimes it is about getting growth that is understood when they eventually leave the company. They will leave and that is totally normal.

    1. Anonym*

      This point about ensuring role titles (and hopefully comp) match responsibility in a way that the wider industry will understand is extremely important, and I’m not sure it was raised anywhere else. You don’t want an employee’s time with you, however long it is, to detract from their overall career trajectory.

  56. Brett*

    When I started work consulting with a smallish startup, they gave me a relatively short presentation up front that included:

    Their history (including their many failures)
    Their current business model
    Their ideal future business model
    Their revenue and funding (including “friends and family” funding)
    Their current level of risk
    Why they needed someone new in their company (this was extremely helpful)
    What previous consultants had done for them
    What they felt they were currently missing as a company

    Obviously this took quite a bit of work to put together, and had to be updated regularly, but they were very successful in hiring the people they wanted across many different types of roles. It also allowed them to run more sanely than a lot of similar startups (they still suffered some from the broculture that many tech startups suffer from), as this sort of regular updating gave current employees clear insight into the state of the company.
    The business model did not work out and the company eventually contracted down to a one-person company under a different model (but making six figures), but the transparency not only showed they were not dysfunctional but definitely helped root out disfunction when it showed up.

    1. Letter Writer - Katie*

      This is a really good idea, thanks for sharing that! I’ve actually made a note of all those headings to use in future

  57. Miss V*

    Generous PTO, and make sure it’s actually possible for them to take it.

    I worked at a small business for for years and was given a measly one weeks vacation time. On top of that it was a fight to even get to take the time off and there were two years in a row where I was told I wasn’t allowed to take a vacation because the only other employee who could cover my job was pregnant.

    It’ been almost two years since I left and I still have such ill will toward the company I actively discourage people from doing business with them.

    1. cmcinnyc*

      On this, I interviewed once for a part-time job at a tiny nonprofit. I was pretty much a shoo-in for the job based on references and connections. But when we talked about PTO… there wasn’t any. At all. On paper, I had set hours and days and could take up to X sick days and Y vacation days. But in the discussion, which thanks all the stars was pretty frank, the woman interviewing me made it clear that the place couldn’t run if people took days off. At all. Ever. So… no. Bullet dodged.

  58. Sunflower Sea Star*

    I’m not a small business owner, but I’ve worked for a couple and from the crazy I’ve experienced, I have some ideas from the employee side:
    Always remember:
    1. Your employees don’t care about your business like you do, and THAT IS OKAY. They’re allowed to do their jobs and go home. They don’t have to give as much to the business as you do.
    2. This is a business, not a family. Do not treat it like family. Do not have political discussions at the company meetings. Do not bring your religion to work and have prayer at company gatherings. Do not expect that you have the right to know why an employee went to the doctor, or what the prescription she submitted to the FSA is for. Don’t expect that your religious beliefs can dictate your employees life choices. Your employees are not your children. (and honestly, you shouldn’t even expect those things from you actual adult children…)
    3. Do not expect your employees to feel gratitude or to grovel because you hired them. Don’t make it weird.
    4. Boundaries. Set them for yourself. Follow them. And respect your employees boundaries!
    5. Trust your employees. Don’t micromanage. You hired them for their expertise, trust their input.
    6. Hire an HR consultant/service. You’re going to need outside perspective. You’re also going to need someone who knows the law to make sure you’re on the right side of it.

    1. Free Meerkats*

      Giving this some thought after my post below, I was just coming back to post #2 here.

      Your religion/personal beliefs/creed do not belong in your business, unless that business is religious in nature. The worst run small business I ever regulated had bible verses on all the walls of the workspace, large portraits of Jesus (think ‘Dear Leader’ or ‘Big Brother’ style) in every room – including the bathroom, the only non-business reading material allowed had to be Christian.

      Don’t be them.

      1. SDSmith82*

        As someone who does identify as a Christian- even I find that fundamental approach uncomfortable. There are places that have successfully made that part of their identity, but they are upfront about it, and make it part of their company culture. I am a pretty middle of the road Christian (one might even say “liberal minded” if they were the ultra conservative sect-even if I’m too conservative for the liberal side) BUT- leave religion at home.
        Unless you are a christian retail store, just treat people well without deliberately bringing politics and religion into it.

    2. Kelly L.*


      If a large part of the company is made up of your family, be willing to consider that members of your family might be in the wrong if a dispute comes up.

      And don’t try to parent the employees who aren’t your relatives. You don’t get to tell them who to date or what religion to be or what diet to be on.

  59. SDSmith82*

    As someone who left small businesses and NEVER wants to go back- I have to say that there are a few things that I see as an outsider.
    1) Know your industry, its pay standards, it’s “trends” and it’s future outlook. Don’t be afraid of change, and don’t do things “the way they’ve always been done”.
    2) Don’t be afraid to fire people. Giving one person a PIP for 3 years in a row, then realizing they can’t do the job and pushing their tasks onto other people, but never firing them is not the way to run things. You just create bitterness. Also- don’t make that poor performer your highest paid employee- cause when that comes out (due to a really bad HR consultant) it really makes the rest of us bitter.
    3) Hire GOOD HR. Someone professional enough to be honest about things, and not sugar coat it.
    4) GIVE PEOPLE RAISES. Annually-if possible. And if their job changes, or they take on additional duties, compensate them for it. Don’t just expect a pat on the back to work.
    5) If you say “open door policy” MEAN IT.
    6) If more than 25% of your staff has an issue with something/someone- it’s an issue that needs addressing. Even if its ridiculous. Having a good HR person can help you handle it.
    7) Trust your employees. Try not to micromanage, and encourage them to soar. But again, when they do- PAY THEM ACCORDINGLY.

  60. Sleepytime Tea*

    I was the only employee to an entrepreneur running her own business. I worked out of her home office. Rule #1 (unless the role is personal assistant): do NOT ask an employee to do personal things for you. She asked me to unload her groceries once. I immediately said no. I’m here to work for your business, not your household. Rule #2: Do not dangle my paycheck over me. She would want me to stay late to do *one more thing* when it wasn’t an option. If that happened to be on pay day, she’d write the check in front of me but not sign it, and then practically hold me hostage to doing whatever it was she wanted in order to get my paycheck. Rule #3: Be legitimate. I was paid under the table, amongst other things. No. Your employees need to fill out W4s, You need to have laid out policies about attendance, dress code, overtime pay, etc. Even if those policies are super short and seem unnecessary, have them and follow them. It takes a lot of guesswork out of the equation. You’ll come off as prepared, ready to grow, professional, etc.

  61. OhBehave*

    Having owned a small business for years, a few insights:

    Don’t expect your employees to have the same passion as you have for your baby. Respect the work/life balance most people need.

    You’ve done things your way forever. There just might be a better way, be open to new ideas.

    Please don’t blur the boundaries of boss/employee. You did not hire them to sit at your home to wait for a repairman, etc. Now, if you make that one of the “other tasks as needed”, be upfront about that.

    Do not expose them to your family dynamic. Keep fights out of the office. Close the door if you’re having a heated discussion. They are not your counselor.

    Have a clear task list for your employee. Train them thoroughly and then leave it in their hands. No micromanaging please!

  62. Free Meerkats*

    I’ve never been employed by a small business, but I’ve regulated many.

    If you have a regulatory burden (financial, environmental, etc), hire a person who knows the field and make that their primary responsibility. So far I haven’t put anyone out of business, but it was close in one case – entirely because they didn’t know what they didn’t know, and didn’t have the time or expertise to comply with the federal regulations.

  63. pinfu dora*

    Honesty is of the utmost importance from interview and job posting, to the offer stage, and should continue through employment.

    My current company is <15 employees and the owner has a habit of telling people they'll get their salary they are trying to negotiate through a bonus structure with averages in the 10 – 15% of salary range and make an offer 10% lower than the target. Reality is the higest tier gets 20%+ and the rest of us are lucky to get 5%. We have quarterly meetings with the owners about the finances and get to hear about how profitable we are and what a good job we are doing and the words feel like a slap in the face.

    The company used to just be those people at the top… and I think they don't see a problem with it because they "paid their dues" through the lean times where there weren't a lot of profits to share and no bonuses were paid. The rest of us are insulted by the bait and switch and 50%+ of the non-management staff are looking for new work. The longest employed non-management person has been here only 3 years or so and 2 people have already departed in the past month.

    As you bring on people and grow, you can't use the same entrepreneurial tactics of trying to get the most work and talent for the least money, especially if you veil it behind empty promises. You'll just get turnover which is the worst for small businesses.

  64. FormerFirstTimer*

    Remember, you might have a good big-picture view of how things are running, but your employees that do the same thing every day are going to know what’s really going on in the weeds. If they tell you something is off, listen to them. My former boss ignored people for 6 years about the same thing and it got so bad that he just had to lay half his employees off without any warning.

    1. FormerFirstTimer*

      Also, and this probably goes without saying: If someone has a felony conviction involving some form of theft, maybe don’t give them access to all the financials with power to purchase and take out business loans.

      1. Elenna*

        …I have so many questions about the story behind this. Most of them boil down to “what were they thinking???”

      2. Gazebo Slayer*

        Yikes on bikes. Definitely do a criminal background check for anyone who will have access to large sums of money!

  65. Jamie*

    If you have an unusual workspace make sure to disclose this during the interview, including with temps.

    I temped at a very small business once, run out of the owners home. In a very weird basement in dim lighting with only one outside entrance/exit, through a maze of rooms working in very close quarters without a clear exit path with a total stranger unnerved me. I left early and was one of the few assignments I didn’t complete.

    I don’t know if the guy was legit creepy, or it just felt that way due to the environment but every time he’d lean over me to point out something on my screen and press against me I was screaming on the inside. No idea if my fear was valid or not, but it was real.

    Just saying if you have a wonky work environment tell them upfront as not everyone wants to be completely alone and isolated with a stranger.

    1. Just Another Manic Millie*

      I used to work at a very small business (five employees, including the owner and me) with an unusual workspace, but it was the elevator that made it so unusual.

      The company was on the 23rd floor of the building. I had no problem getting to the office or leaving when I went there for my interview. But on my first day, I got into the elevator, and when it reached the 23d floor, the bell rang, but the door did not open, and the elevator suddenly plunged down to the ground floor. I got out and told the lobby guy what had happened. He said that it happened all the time, and he said that what I had to do was ring for another elevator and keep trying to get to the 23rd floor, because eventually, the elevator door would open, and I would be able to get out.

      I eventually found out that if someone on the elevator with me wanted to get out at the 22nd floor, he/she would be able to get out, but then the elevator, instead of going up to the 23rd floor, would go back down to the ground floor. So I learned that when the elevator stopped at the 22nd floor, I should get out and walk up one flight. I also learned that when it was time to leave, I should walk down to the 22nd floor to get the elevator, because I could not count on it actually getting up to the 23rd floor.

      I’m just sorry that the elevator worked just fine when I went there for my interview, because if I had known at the time what a hassle the elevator was (especially when all three of them went out of service at the same time, and it lasted for weeks), I wouldn’t have taken the job.

  66. computer geek*

    Companies I’ve worked at:

    * 7,000 public employee company with revenues just under $10B/yr
    * several public/private 300 employee companies
    * 100 private employee company
    * 20 private employee startup
    * 5-10 private employee company

    By far my worst experience was at the 20 employee startup: dysfunctional management who lied.

    My current company is the smallest one, and it’s been a great experience so far. I believe my experience at the larger companies have helped me understand what is sane and what is not. I wouldn’t recommend this as a first job. I also know that a huge company is not for me. I enjoy seeing my contributions impact the business.

    Things my current boss/founder does correctly: We have open financial books. At any time, we can open a spreadsheet and see the health of our company. We are trusted to keep this confidential. We have regular meetings where we talk about where we are at financially, where we are going, and any potential issues. He’s open and honest. I know where I stand with him. I don’t have any reason to doubt what he says.

    He’s also insanely brilliant, and that’s sometimes intimidating. I’m used to being the smartest person in the room. I’m not any longer. I suspect that’s a key to my happiness with my ultra-small company. I feel challenged. If I didn’t have the utmost respect for my boss, I’m not sure I’d still be here. We’re small enough that you can’t hide incompetence.

  67. Antti*

    My answer’s more focused on food service, since that was the one small business I worked for, but I think some things are still broadly applicable.

    Empower your employees to do what you need them to do. It sounds obvious, but in my case, I was often staffing our coffee shop alone, and after a bad experience in a past attempt at the business, my boss made it so he was the only one who could open the safe. Sounds ok, but it meant if I was ever running low on change, he needed to be there to make it, or I’d have to put a sign up begging people to only use small bills, etc. My coworker came in on her off day once when this happened, and I had to beg her to clock on to mind the shop while I ran to the bank. (Not good practice, I know!)

    Don’t do too much too soon. Part of the toxicity of working there was from customers being (understandably!) annoyed/angry that they could never get more specialized items on the menu because we never had the supplies in stock.

    Related, make sure your basics are covered. You cannot run a coffee shop and be perpetually out of vanilla or caramel syrup, or out of chocolate. You cannot expect that your customers will be willing to overlook such fundamental shortages.

    If you have more than one business, make sure all your money is in the correct place at the right time. I had more than one paycheck bounce not because he didn’t have the money, but because it was in the wrong account.

    A lot of this sounds like the fundamentals of running a business, yes. But that’s exactly it…make sure you are operating according to best practices at a bare minimum, or else you are guaranteed to create a toxic and/or stressful work environment. There’s more than that to it, of course, but if you seem unstable or like you don’t know the first thing about running your business, you’ll be lucky to have employees at all.

  68. Nesprin*

    Specific to technical startups perhaps- have a designated devils advocate in each meeting, and have that person rotate. You want to make sure that everyone is willing to raise concerns and that they’ve had the practice of being on both ends. Nothing kills creativity like yes-men.

  69. Dysfunctional Deb*

    Because I grew up in a family I now realize was very unhealthy, I did not recognize signs of dysfunction in my first workplace.

    I can only suggest managing with honesty and integrity, by having a basic understanding of Human Resources, interpersonal communications, and operational dynamics as well as financing, employee review and progressive discipline, etc.

    What about assembling a group of experts you can turn to for advice?

  70. The Original Stellaaaaa*

    Honestly, do an online business degree or certificate. Most issues with small businesses stem from the fact that the owners are lacking the relevant education/information. This isn’t about being naturally intelligent. There are specific facts and processes you need to know about, and intuition and guesswork won’t cut it.

    1. Delta Delta*

      This is a very good suggestion. I’m a lawyer, and in my legal career have only worked for other lawyers. I’ve figured out that lawyers are good at lawyering, but tend to be rubbish at running businesses. AND they tend to think they know everything and refuse to learn how to run businesses, or that being a lawyer is enough to know how to run a business. I suspect this may be true with other professions, but I don’t know.

      1. The Original Stellaaaaa*

        I’ve worked for a few businesses where the owner started out by like…selling things out of his garage, and then he decided to just hire people to help him out. They have no idea that you generally have to get employees on the books within 72 hours. The don’t know that you legally have to supply bathroom soap and a source of drinking water. They don’t know that there’s a limit on how long a paycheck can be delayed. Selling a good product is just one piece of the puzzle.

        1. MsSolo*

          Yes, and I think a lot of small business owners don’t want to confront the fact that running a business is a full time job that’s not the same work as what the business actually does. If you like selling things, either hire someone to do all of the business management elements, or resign yourself to not being the one that gets to talk to customers any more.

      2. The Man, Becky Lynch*

        “I suspect this may be true with other professions, but I don’t know.”

        Yes. Doctors and engineers tend to have extreme difficulties running businesses as well. They think they’re brilliant [and they are usually, only in their very specific specialties though…]

    2. The Man, Becky Lynch*

      Bosses with a “business” background have been the worst people to work for on a small business scale.

      They don’t understand how to scale for the size of their organization, they think things are all straight from the book and how they were taught in school…and they are also pretty hard to communicate with if you’re dealing with a business that has a lot of workers who don’t require any kind of higher education.

      So it depends on the kind of business you’re opening when it comes to if a degree and education is needed.

      1. The Original Stellaaaaa*

        It’s better than working for someone who’s never taken a basic business course. I don’t see how that can be argued with.

  71. pally*

    Be upfront regarding the benefits you do and don’t offer. And with any plans to add more benefits as things progress. This may or may not be the deal-breaker you might think. Some folks have other avenues for benefits like health care, dental, etc.

    I went all the way through the hiring process for a place only to discover no health care benefits. Not one person ever thought to tell me this. They acted like “Why, yes! We have benefits!” But they never were specific until after the offer was extended. I asked to read the employee manual. They said they needed to get their attorney’s approval first.

    (yeah, red flags!)

    So I get the employee manual, find the lack of benefits-no health care, 5 paid holidays, 5 days paid vacation, and … that’s it!
    So I thank them for their time and extend my best wishes that they find a good fit for the job.

    1. Just Another Manic Millie*

      “I went all the way through the hiring process for a place only to discover no health care benefits. Not one person ever thought to tell me this.”

      This sounds just like a company that I once applied to. During the interview, I asked if they had health insurance. The interviewer snapped, “IF we decide to hire you, THEN we’ll tell you about our health insurance!” And then he glared at me to let me know that I was out of the running because I had merely asked about health insurance. Maybe that’s why no one “ever thought to tell you this,” because they were waiting to see if you were the person they wanted to hire, at which point they were going to tell you.

  72. Delta Delta*

    I hope not to repeat too much what others have said, but here’s what I think would be helpful:

    1. Don’t mix personal and business finances. Make sure you’re paying people out of the business account and that the account is current. Don’t use business money to pay for something personal. It’s hard to track and it feels shady.

    2. If you have another business – let’s say you own a florist but you also own several apartment buildings, a laundromat, and you flip classic cars (not that this 100% a personal experience or anything), keep your businesses separate and don’t expect the employees to know what’s what. If you have floral business, do that at the florist. And don’t yell at the florist if she doesn’t know anything about the 67 Chevelle in the parking lot. And don’t expect the florist to conceal your whereabouts if you’re hiding from a crappy tenant. I could go on, but you get the point.

    3. Be upfront about your financial situation. It helps employees to have context to know about the business and what’s reasonable that could be done (or not) based on the financial situation. Corollary: if you rely on significant contracts to run your business (let’s say you’re the contract florist for the nearby university), do not tell your employees that if the other side doesn’t negotiate differently that you’re dumping the contract. Things like that strike absolute terror in employee hearts, and makes them wonder if they have jobs.

    4. Have job descriptions, but also be open to feedback from people doing the jobs about what works and what could be changed. If you hire an assistant and she makes suggestions to increase efficiency and/or happiness, listen.

  73. WantonSeedStitch*

    Be clear on constructive feedback and don’t get emotionally involved in it. Emotional neutrality can be harder to maintain when you’re working closely with the same small group day in and day out, but being able to communicate in a calm and professional way is still vital! Likewise, don’t just assume that because you have amiable interactions with someone on a daily basis that they are aware they’re doing a good job. Instead, make a point to provide positive feedback that’s specific and clear.

  74. banzo_bean*

    I have worked in small tiny businesses almost exclusively for the past 10 years, and I’ve always worked in administrative setting. Here are my experiences:

    1. It can be hard when your boss is also the owner of the company. When they’re a jerk, unfair, breaking employment laws, etc there isn’t someone to which you can escalate the situation for conflict management/mediation. Of course when it’s things that are serious, like refusing to pay fairly or give breaks, the employee can contact an outside agency but that can be especially un-appealing when you’re the only other employee.

    2. It will of course always be YOUR business and YOU baby, but you have to let a bit of that attitude die when you hire on employees. That doesn’t mean you give up your decision making authority or your control over the company’s mission, but you have got to recalibrate and realize your business is now a collaborative effort. Even if you’re only hiring on a receptionist, you’ve got to view yourself as part of a team. The leader of a team, yes, but still a team. So if someone approaches you with an idea or problem, you should openly and earnestly listen to them.

    3. Speaking of which, you will 100% always work more and care more about the business than your employees. It’s not because they aren’t committed enough or don’t care enough, it’s because it’s your business. Would you ever yell at your friend who babysits for you because they don’t love your child as much as you do? Don’t do this to staff- its demoralizing.

    4. Don’t fall into the trap of “I know this would never fly if we had more employees /or a one woman employee / if the employee wasn’t my best friend.” Because that makes it harder to grow and change.

    1. Mama Bear*

      #4 – We had to have some HR training that I later found out was because some of our team forgot they weren’t in a frat house. While I wasn’t personally offended, the big boss rightfully recognized that they were on thin ice as the company grew, so harassment training became required. What’s the saying, “start off as you plan to continue”?

  75. Signel*

    A thought: be businesslike. I’ve seen many people run their small business like a hobby, not a business.

  76. My Brain Is Exploding*

    All great advice so far. My experience is in health care, and you may want to consider hiring two overlapping part-timers v. one full-time timer (of course it depends on your business).

  77. WoolAnon*

    I’ve worked in a tiny business before (few years back) and, unfortunately, it’s why I would be very leery about working for a two-man operation again. Everyone’s already said most of what went wrong there (primarily boundaries, but also knowing HR/employment law (ironic part is he was an employment lawyer) and reasonable pay/yearly raises), but I would add to not do anything you would think of as a ‘favor’ for your employee. Remember that it’s solely a business relationship.

  78. nnn*

    Some tips based on mistakes I’ve seen small business owners make:

    – Don’t expect employees to have the same passion for your business as you do, or to be able to make sacrifices for your business. If you want someone who’s as all-in as you are, you need, at a minimum, a joint partner who shares in the profits and has decision-making authority.

    – If you need your employee to be better at stuff than you are, you need to pay well. (Where “well” is defined by the quality of life the employee can buy with the salary, not by what the salary does to your margins.) Don’t complain that the teenager you hired as casual help is unable to create a flawless organizational paradigm for your storage room, and then complain that they left to go work at McDonald’s because it pays more.

    – Make a plan for if you become ill or incapacitated. You want the employee to be able to keep the business running and keep serving customers, rather than standing around helplessly not empowered to do anything.

    1. emmelemm*

      I’m having that problem right now. I work for a sole owner as currently the sole employee. He is about to have surgery. If something happens, my ability to serve our clients will be nil, which is a) bad for them and b) bad for me, since my references to move on to something else will have to be clients I’ve worked with for years now, and if they’re unhappy at being left in the lurch, well… But of course it’s difficult to get him to realize this.

  79. ellis55*

    I worked for a non-profit where it was just me and the ED. Being a 2-person of even 10-person shop can be intense – you spend a lot of time with you and the other person, you go through every up and down together. Just like in any relationship where you spend a lot of time together – a friendship, a marriage, etc. – you will find yourself getting very sick of, and frustrated by, this person sometimes when you need to be understanding. You may also find yourself very protective of them sometimes when you need to be stern or skeptical. You can’t prevent that entirely, but you should be aware of the ways that affects your decisions and try to correct for it.

    The best advice I can give is:
    1. Cultivate more professional distance and structure than you think you need, at least at first and for a good long time. You can be warm, but you shouldn’t be friends with this person, which will be very tempting because you’ll likely have a lot of bonding experiences together. Remind yourself that work relationships can feel very immediate but it’s mostly a function of being around one another so much, and you are absolutely headed for a crash if you get too close and then for whatever reason now you need to discipline them in some way. It will be harder on you and feel entirely too personal for them. The environment will get very toxic.

    2. On that note, be fair and market-appropriate with benefits and perks but always ask yourself, “If I had more employees, would I let them all do ‘x’?” It’s so easy to get attached to one person and feel like they would never abuse ‘x’ privilege – and maybe they won’t! But as you grow, you don’t want to have one person the rules don’t apply to that everyone resents. Also remember that it’s so much harder to take something away (like working from home or bringing a baby to work) because you now realize it doesn’t work for you than it is to never offer it in the first place.

    3. Talk to them about their long-term goals, and really listen. Assume that if what you’re offering doesn’t fit in with that, they will leave someday and don’t make them feel like you will somehow not be okay if that happens. If you want your employees to be honest with you, you can’t make a very common truth (people move on!) seem like an outcome you couldn’t tolerate.

    4. You will likely end up knowing a lot more about this person’s life than most bosses do. Remember that some things are not your business and shouldn’t affect your decisions regarding them. For example, if your employee is bad with money, in your opinion, that has nothing to do with whether or not you should offer them raises for performance or cost-of-living adjustments.

    5. Admit when you share the blame for something, if you genuinely think you do. In relationships where one person has all the authority and the other has none – and neither of them have any peers on their level – nothing erodes good will faster than feeling like the person with the power is your adversary vs. it’s both of you against the problem. Non-defensive communication is a part of that. If you want your employee to own their mistakes and be solution-oriented, you have to model that. It’s hard to do when you always reflexively understand your own reasons for doing something the way that you did, but it’s a good practice to not get to wedded to your own perspective, especially when there’s no one on your level to check you.

    You sound thoughtful and ready to avoid many common pitfalls. Congrats on the growth of your business!

  80. Blueberry Smoothie*

    In all honesty – get some therapy. I see a therapist who is also a business consultant, and they say that in a small company, the company dynamics will replicate the dynamics of the company owner’s family of origin unless they deliberately make different choices.

    Know what you bring to the table; what your unspoken assumptions about relationships in which you have more power are, how you handle anger and stress and how you project those onto other people, what you expect of someone who is in many ways dependent on you and not as free to stand up for themselves in conflict as a friend or family member would be. Know what your usual transference reactions are. Know what your gender, racial, and class assumptions and issues are.

    Mix that self-knowledge with solid standard business knowledge, and I think you have a better chance than most at building a healthy small company.

    1. Hex Code*

      Yes!!! What does a “good” relationship with an employee look like to you? What is your preferred method of communication? And on and on. Having self-awareness about these aspects of yourself will, for instance, allow you to articulate to employees *why* you prefer things a certain way instead of them having to intuit how they should approach you.

  81. Peter Piper Picked a Peck of Pickled Peppers*

    Based on my own and my husband’s experience interviewing/working for smallish companies.

    Don’t offer benefits that you can’t maintain. My husband’s company cut everyone’s leave by 5 days, because they had grown and it became “too expensive”. A year or 2 later they introduced a great new scheme, where everyone… could… you guessed it, buy an extra week of leave.

    Respect people’s privacy and boundaries. These are all horrible examples which no sane person would do, but here goes:
    Do not try to convert them to your religion. Do not have “friendly” theological debates. Do not tell them you’re worried they’re going to hell.
    Do not demand that your employee’s spouse attends the end of year function.
    Do not have a theological debate with your employee’s spouse at the restaurant.
    Do not expect your employees to sleep at your house when they travel to your city on business, and eat breakfast in your kitchen with your wife.
    Do not call your employees at 10pm and on weekends because that’s when *you* happen to be working.

    Above examples all courtesy of my husband’s company.

    Do not demand to meet your potential hire’s spouse during the interview process because “we’re like a family”.

    Don’t make promises during the interview process that you have no intention of keeping, or even that you think you’ll keep but haven’t really thought through.

    Don’t give your employees unclear instructions and then rage at them when they get it wrong.

    Don’t hire your family or members of your religious community, give them preferential treatment, and expect your other, more competent staff to stay motivated and enthusiastic.

    Don’t make your employees work from a room at the back of your house and have to go into your kitchen to make a cup of tea.

    Don’t talk about your holiday home and your overseas trips unless you are paying your employees really well.

    Okay, some examples that are less ridiculous.

    Stay on top of your admin. Don’t forget to send out payslips, until your employees ask for them.

    Don’t pay your employees on a random day in the last week of the month. Be consistent.

    Provide more rather than less information about what your employee is expected to do, what the norms, processes and expectations are.

    Be critical about your strengths and weaknesses and close the gaps by hiring an accountant or getting coaching on how to manage employee performance. Don’t just stumble along and hope for the best.

    Think carefully about how you plan to scale. Rapid growth is something that most company owners hope for and are generally poorly prepared for.

    Good luck with your business venture!

    1. frystavirki*

      I was going to say, “please tell me those horrible examples aren’t all the same person,” but then I realized I’m not sure if it’s worse if those horrible examples were all the same employer, or if they were all different horrible employers. Like, is it worse to have one Small Business Owner From Hell or a bunch of them that had separate “my employer is awesome except for this one horribly egregious thing” advice letters waiting to be written? (I still kind of want to know whether it was just one dude. If so, oh my god I’m so sorry.)

  82. Mama Bear*

    Another one I just thought of:

    Have a plan for raises – don’t make a person beg for a raise and don’t make the process a big secret. If you’re doing reviews like you should, then that’s a time you can discuss performance and money. If you can’t do raises because money is tight, be upfront. See if you can offer another perk like telework or an extra floating holiday.

    I didn’t get a raise at one place in nearly 3 years. I did get a bonus (direct from the big boss/owner) but that was taxed heavily and wasn’t the same as an increase to my salary. I appreciated the gesture, but would rather have had the raise. Not getting a raise again (while being privy to the contract negotiations with the client) was a factor in my departure. Also, and this goes back to being upfront and direct, my bonus was just suddenly in my check. There was nothing in my personnel folder to indicate I’d done a stellar job.

  83. Ra94*

    As someone currently working at a small business that’s a veritable glacier of dysfunction: boundaries! I think when you work so closely with people, it’s easy for things to blur: not just appropriate conversational topics or emotional oversharing, but things like blurring the boundaries of roles. What tasks does the assistant do? If you hire a second person, how are their tasks differentiated? (Don’t do what my boss does, and send out tasks to both people asking that ‘someone do this.’)
    And on a personal level, even if you’re close with your employees, don’t lose sight of your responsibilities as an employer. No matter how friendly you are, there’s an inherent power imbalance, and especially be wary of complaining about financial issues that could come off tone-deaf. (I.e., my employer asking us to deposit our paychecks late because she’s ‘so broke’ from booking a ski trip.)

  84. Richard Hershberger*

    I am a paralegal. I work for a guy. There also is a secretary. I have been here ten years. The secretary was here when I arrived. It is very functional. The legal business might be different from others. Solo practitioners are common. A solo practitioner who has support staff is a sign that he is successful: he has enough work that he needs the help, and his work pays enough that he can pay us.

    Paralegal is an odd job title. It is very underdefined. If I meet another paralegal, I have little idea how he spends his day. I have a better idea if it is a personal injury paralegal, but not much. If it is a personal injury paralegal who works for a solo practitioner who also has a secretary, I can make a stab at what this person does, but it may still be something different from what I do. So what does a paralegal do? If working for an attorney who is also a good boss, the answer is “everything the paralegal is capable of doing,” short of showing up in court wearing a suit (and even that, occasionally, but not alone). The whole point for a lawyer of hiring me is for me to take as much off his plate as I can. I am very good at drafting pleadings that are mostly fact-based: less so with pleadings that are mostly law-based. So the fact-based pleadings, or the factual part of other pleadings, I draft. He is perfectly capable of doing this, of course, but why would he when I can? And so on. And yes, there are days where I end up filing and answering the phone. That happens occasionally in a small office.

    This works because we understand each other. At this point in our relationship our expectations of one another are very realistic.

    Also, he is a mensch. His former employees from decades back pop up occasionally to have lunch. By way of contrast, my previous job was three years working for a guy with only a slightly larger practice. It was a very long three years. He was later disbarred. Were I a better person I would not have read with such pleasure all 100+ pages of the judicial decision.

    So I guess what I am circling around here is that in a tiny business you will be cheek by jowl with one another even more than in a larger organization. It is all about how the individuals get along and get work done together–again, even more than usual. It is, therefore, even more important than usual to figure out how to combine a professional relationship with what will inevitably be a personal relationship.

  85. That Would be a Good Band Name*

    You are going to want to hire someone before you have enough for a full-time person. At least, I’d assume you will unless you are going to wait until you are working 80 hour weeks to hire someone. Have a plan for what you want you employee to do. Be paid full-time even if there isn’t a full day’s work every day? Be part-time until the work ramps up a bit more? There is nothing worse than being hired for a full-time position to learn that it’s really only 2-3 days of work and you won’t actually get paid what you expected.

  86. Hmmm*

    You are already doing a great job by asking this question. As someone who has worked for a number of small companies with various levels of dysfunction I can say three things made all the difference:

    1. Examine any unconscious bias you may have before hiring. Diverse hiring early on sets up the company for more effective growth and ideas moving forward. This goes beyond race and gender and includes any ableist assumptions you may have. There are free videos on YouTube about how to tackle this. One of the ways that’s helped me is to initially print out resumes and fold over the part that has the name so I only see their experience. It’s not perfect but I definitely noticed a change in the types of candidates that got phone interviews and in person interviews.

    2. Document current processes in place and think seriously about how you want to on-board the new employee. The more structured your on-boarding process is the better tone you will set at the beginning. Small businesses have a tendency to throw new employees “into the frying pan” without formal training or expectation settings. This sets the tone that documentation and transparency are not critical, creating silos of information early on.

    3. Have realistic expectations regarding salary, experience, and education. If you can only afford a part-time employee’s salary then only hire a part-time employee. Is having a specific bachelor’s degree or having a bachelor’s degree really that important? Or a certain level of experience? The answers can be yes but really think about what you are asking and weigh it against the salary you are providing. Also, consider your plan for salary increases and bonuses then put them in writing.

    There are more factors to success but I have found these 3 tend to create the foundation of a successful company.

  87. Bookwerm*

    Take some notes from larger companies about setting fair policies regarding working conditions, paid time off, sick leave, vacation time, dress codes, working hours, etc. I worked for a small family-owned company and everything was a negotiation. If I needed a day off for my child’s birthday party, or when he was sick, I had to beg for it from the owner. It was demeaning! And since everyone was doing this, all decisions were inconsistently applied. So one person would get three weeks of paid vacation (because they asked for it), while another got one (because they didn’t), one person got permission to leave early every day to pick up a child, but others didn’t. And so on. So even if you only have one or two employees, borrow a company handbook from somewhere else to use as a guide for the type of information that should be included, and create your own. Then you use can use as part of new-employee orientation, and as you add employees, it will become even more valuable. That way you’ll be sure you’re being equitable with your staff.

  88. Lefty*

    I actually enjoy working for small businesses and have for the majority of my career. Most of the them have been simply quirky vs badly managed, but I just noped out of a small business job I had for about 6 weeks. It was so bad I quit with nothing lined up.
    Here’s my list of suggestions based on my most recent experience. As an owner, your goal should be to hire quality people who want to stay and help grow your business. If you’re having trouble retaining good people, you’re doing something wrong.

    1. Don’t lie about anything at all, ever. Also, don’t bait/switch job descriptions or schedules.
    2. Don’t string people along–don’t say you have big plans to change processes or get more clients when you have nothing, not even a timeline, to back it up.
    3. Don’t mess with an employee’s tax forms and paycheck because you *think* they filled out their own exemption worksheet wrong. Seriously. Don’t change someone’s exemptions.
    4. Every once in a while, say every year or two, review what you are doing. Review your processes. Are you doing things efficiently? Are you doing things that make sense? Is everything you’re doing necessary? Don’t fall into the trap where you’re doing things the same way for 30 years because you’ve always done them that way. Be open to new ways.
    5. Train your people. Do not tell your employee that they won’t ever be fully trained because it would take too long. If you delegate basic training to another employee, make sure that other employee doesn’t feel threatened and trains your new hire wrong on purpose. As a whole, if your staff knows that they are doing, let them go free. Please don’t ask them to print (!!) every email and document for your review before they are allowed to send it.
    6. If you have feedback for your employee, especially your new hire, talk to them about it. Do not print a memo about it and hand it out to the entire staff. Especially if your new hire didn’t really know there was an issue to begin with. Also, be willing to have closed-door meetings with your personnel. Not everyone in the office wants “the family” to know all of their business.
    7. Give your people the equipment/tools they need to actually do their job. Example: If you have two admins with different roles who both need a computer, budget for an extra computer. Please don’t expect two people to share one computer for an entire shift day-in and day-out. Also, don’t go from, “we’ll set you up with a computer this week” to “there’s no money in the budget for a computer,” unless you want someone to panic about whether or not they’ll actually be paid the next payday.

    1. Natalie*

      #3 is actually illegal – unless you receive a lock-in letter from the IRS, you have to use the allowances, filing status etc, the employee provided you.

  89. JJ Bittenbinder*

    My least favorite recent job was working for a small (5.75 FTE and a handful of consultants) business. Now I work for a company that employs over 80,000 people.

    The biggest thing I bristled against in the small company was interpersonal issues and how they played out in the workplace. While some of it was a personality thing (if Debbie is a gossip, she’s going to be a gossip in a large company just as much as in a small company), the impact on a work environment with only a few people is much larger. There’s no buffer. In the year that I was there, I was fortunate enough to be well-liked and therefore not the target of the gossip and backbiting, but I knew it could turn on a dime and I’d be the odd one out.

    So, think about the realities of scale, and the behaviors you will and will not tolerate, how you communicate that, and how you manage it.

  90. Aspiring Chicken Lady*

    One thing I’m not seeing much of here is … if you’re hiring someone to do something — give them the authority and space to do it.

    Hiring another person isn’t the same as creating 8 more hours in the owner’s day. Carve out the responsibilities and duties, and then don’t get micromanage-y if they do it in a new way.

    1. KR*

      Yess to your last point. I knew it was time to leave a job when they hired a sex offender as a manager for a position with underage food service employees. A sixteen year old girl reported sexual harassment to the owners and she got her hours cut in retaliation which is of course completely illegal. 16 yr olds parents got involved and it turns out the owners never even bothered to Google the manager they hired (his sex offender registry page came up on the first page of Google results!).

  91. Red Fraggle*

    Two specific things immediately spring to mind:

    1) If their role is client-facing, then your employees need to know that you have their back. No one likes to be thrown under the bus for doing their job correctly.

    2) You need to be prepared to handle a sexual harassment report. FYI “he’s a married man,” isn’t handling it, nor is “he’s just joking” or “it’s part of our culture.”

  92. drpuma*

    Be prepared to give up (some) control and let your employees do the jobs you hired them to do. I used to work at a small startup where the CEO loved to jump into our CRM and respond to customer emails. He would never close the loop, though, and it only sewed havoc. Also it wasn’t great for my morale that he didn’t seem to realize his time was so much more valuable than that.

  93. Mid*

    Your small business might be your life, but it’s the other person’s job. Even if they’re loyal and committed as can be, it’s still just their job. It’s your passion, and you have a lot more to lose from the failure of the company, but also a lot more to gain from the successes. They shouldn’t be expected to dedicate their heart and soul to the business, unless you’re sharing equity with them. The best way to have a loyal, dedicated employee is to pay them well and treat them fairly. And again, they’re an employee. They’re not your family. They’re not going to be your 24/7 on-call gofer. Boundaries and respect will go a very long way.

  94. Mrs. Smith*

    My parents ran a small gift shop for many years, and over the past three decades since it closed, I’ve been able to observe and work for many small family-owned businesses. I can say with utter certainty that my parents did it absolutely right and there are lots of ways for it to go terribly, terribly wrong. My parents were very good to their employees, and they were rewarded with good performance. They paid a fair wage, gave them some autonomy, trained them well, and absolutely recognized that while they may have enjoyed working there and liked my parents as people . . . their employees worked *for money,* not any other reason. There was a great employee discount, a nice annual party, and they were upfront about the job being a part-time, no-benefits retail position so that anyone who applied was clear on the concept. There was no “we’re all family here, please ruin your life for us!” crap. Paying the employees was paramount – if there were money troubles, it didn’t splash onto the workers. I’ve seen exactly the opposite of all of these things at other businesses, and although it may SEEM logical – it’s so rare as to be almost shocking when I do encounter it. Way to go, Mom & Dad!

  95. Ayko*

    When it comes to employee perks, benefits, and the way you support them as human beings, make sure you are substance over style. I don’t care if you have a waffle maker, a smoothie blender, and a full stock of amazing snacks in the employee kitchen if you’re not offering health or retirement benefits. I don’t care if you throw expensive, spectacular Winter Holiday parties if I’m unappreciated the rest of the year. I even once got a surprise end-of-year bonus which only made me seethe with resentment, simply because it came off like an attempt to buy my loyalty when they had been showing none to me the entire previous year.

    Also, never make promises without thinking them through. If you’re not prepared to put it in writing, if you’re not very sure that you can deliver what you promised, don’t make the promise. Have a realistic discussion, be realistic about what you know and don’t know, and what your resources are. I was once fired for going to chemotherapy, 3 months after he had promised that he “wouldn’t penalize me for being sick” and that he wouldn’t even dock my sick leave. I had strongly encouraged the business owner to make a backup plan in case I was hospitalized, became too sick to come in to work, or, you know, died; instead he blew me off and said everything would be fine. I didn’t have the mental bandwidth to go chasing after him to try to make him plan for this, since I was extremely pre-occupied with confronting my own mortality. It also was not my job to make sure he took a realistic approach to how it would affect the business and that he could keep his promises.

    And if for some reason your circumstances change despite your best intentions, have an actual conversation with the employee rather than just rescinding your promise and leaving them to deal with the fallout. Come up with a solution, don’t just leave them high and dry.

    1. Ayko*

      Oh also: become very familiar with labor law. A particular problem in my experience is wage theft. Know what the definition of wage theft is. You wouldn’t believe how many small employers have no idea that what they are doing is illegal. Workers are rarely educated on this either, unfortunately — I wish this was something taught in high school.

      Wage theft problems I’ve encountered:
      1. Working through a temp agency: working from home, client insists I’m available at a moments notice (that is, 40 hours per week) but only want to pay for hours I’m actively doing something (aka 5 hours per week). Agency goes along with this and refuses to submit me for any other work.
      2. I clock out, then am asked to run some food to a meeting of corporate muckety mucks “as a favor.” I can’t clock back in without the manager’s code, and the manager is nowhere to be found. What I thought would be 5 minutes turns into half an hour off the clock, because the muckety mucks won’t acknowledge me when I ask who ordered what. (I was then fired for “not smiling” while I ran their food, unpaid.)
      3. Teaching job at a community center was very visibly advertised as $25 per hour (they were very proud of “paying a living wage”). When I submit my first timesheet, they call me and tell me they won’t pay me for more than 3 hours per week, the official length of the class — even though I had already spent an additional 10+ hours making their vague and incomplete curriculum materials into something I could actually teach from. No, I never got paid for that time. Also the classes ALWAYS went longer than 3 hours — it just wasn’t enough time to cover everything and leave time for genuine Q&A. When I attempted to discuss with them, and even pointed out that it was LEGAL to pay a $75 stipend per class (as long as they tracked actual hours and didn’t end up below minimum wage, and they didn’t claim to pay hourly), they quietly removed my class from the schedule and never spoke to me again.

  96. 1234*

    I worked in a few small businesses and one of them has some ahem *interesting* reviews on Glassdoor.

    – Actually have passion for what you are doing. I worked in one small business where it was clear that the owners were only doing this to make money or that being in the industry was “trendy.” They didn’t know anything about what was actually happening in the industry.

    – Employee “team bonding” events and free pizza will not make up for low wages.

    – To that end, pay your employees a living wage that is in line with their job.

    – Give your employees job titles. I was never given a title and was just told I was joining/interviewing for the company’s llama grooming department.

    – In your interviews, please ask relevant questions. I was asked what the HTML for XYZ was when my job didn’t include writing HTML. I knew the answer to the question though.

    – If you ask employees for suggestions, do not do the complete OPPOSITE of what they say without explaining your reasons. You may have good reasons for doing so, but to an employee it just looks like “well, why bother asking for my suggestions if you aren’t going to listen?”

  97. Aunt Piddy*

    I have a nonprofit background (which also comes with its own whole set of icebergs) but the most important thing I’ve found is: hire someone with enthusiasm for the job you are hiring for, not the overall mission/focus of the company. If you are a dog rescue, but are hiring a CPA, hire someone who loves being a CPA instead of someone who loves dogs. The person who loves dogs will eventually be bored or sad they don’t get more time to play with dogs. The person who loves being a CPA will keep loving being a CPA if you run the business right. It’s great if they like the mission or product, but their immediate job has to take priority (that’s how the mission/product gets done!)

  98. Jedi Squirrel*

    This applies to more than just small businesses, but I’ve seen this issue arise at small businesses a lot.

    When you hire, it’s important to hire people with a different skillset than yours. Unless you have a well-written job description (and a lot of small companies don’t), most small business owners tend to hire people with the same set of skills that they have. It’s understandable, because you have something in common that you bond over during the course of the interview, and if there are skills that you need someone to do but you’re not familiar with, you may not even know what questions to ask, which can lead to your asking those candidates the wrong questions. You need to do some research about what the job will actually entail as you write the job description.

    1. Delta Delta*

      YESSSSS! Again, lawyer here. Worked for a lawyer who (for reasons that MAKE NO SENSE) wanted all the paralegals to also have law degrees. Why why why why? The paralegals do different things. Man, I have worked for some really weird people.

      1. JKP*

        Wouldn’t that make them fellow lawyers rather than paralegals? Or did he want paralegals who had a law degree, but never passed the bar exam?

  99. revueller*

    Benefits. Benefits. Benefits.

    By that I mean *real benefits*: competitive wages, sick leave, vacation days, health insurance, etc.

    Consider two bosses:

    My partner (call him Taylor) worked a summer job at a kite store for a friend’s father (call him Dave). Taylor got along with Dave very well, and they stayed extremely friendly for years to come. However, it was very much a Summer Job. Dave hired international students on purpose to underpay them. Taylor made just above the minimum wage, which was enough to pay for seasonal housing in a studio he shared with one other person. Dave was fine and nice as a boss, but the long days, lack of overtime, and the shit wages meant that turnover was high—even for seasonal work.

    Contrast: after college, I worked for a wackadoodle boss (let’s call him Greg) in the TV industry. Greg also only hired fresh grads. He smoked weed in his office, refused to let anyone see his bookkeeping processes, and epromised all sorts of bullshit projects to us every year that never panned out. The industry was hell, with long hours, finicky clients, and abusive guests. However, Greg also encouraged us to use vacation days, paid double for overtime, and gave us free lunch and dinner on longer days. When one woman got sexually harassed by a major TV personality, he went full fucking bulldog on her behalf and promised legal protection if it ever happened again (he wasn’t there the first time it happened). There was no advancement possible within the company, but the boss had positioned many, many people to move up in the industry through networking.

    Both bosses are still in business. Dave taught my partner what a summer job looks like, while Greg showed me what a career could be. Taylor will never work for Dave ever again, while I probably would put up with one (1) shift with Greg (even though he laid me off) because of the respect he gave me in his fair wages and benefits.

    Best of luck, OP.

  100. Andie Elizabeth*

    If you hire someone to manage other employees, you need to leave time in their schedule for management tasks! Reviewing performance, coaching, observation, etc. are all things that take time. A big problem for my current small business is that the owners hire managers, or promote individual contributors to a “management” role, but expect them to keep putting out the same amount of work tasks that they’d been handling before, and also managing people in the nonexistent free time around the edges of that. It doesn’t work and everyone’s frustrated.

  101. Penguin*

    Support your employees! Not just with appropriate compensation and clear expectations, but with actions that allow them to do their best jobs supporting you and your business. For example:
    1) Don’t ask an employee to do something illegal. This includes “little” things like “creative” time sheet recording and speeding.
    2) If an employee has to do something that customers won’t like (collect a new processing fee, require additional forms, release product samples only to established customers, etc.) be upfront with customers that these are your policies and hold that boundary. Don’t say “oh, I don’t know why [employee] told you that, it’s not our policy” (if it IS your policy) because you don’t like conflict or are afraid of losing the customer.
    3) Recognize that humans work better when they are treated humanely. This is a hard truth, but it’s in your own best interest to recognize that your employees cannot operate under constant strain AND do their best work. (Machinery can’t either; both your printer and your staff need preventative maintenance and downtime.) Build this into your expectations and plans.
    4) Don’t try to take shortcuts by externalizing your costs. If you require an employee to work overtime, pay them.
    If they must use a personal vehicle for work travel, compensate them. If you need business supplies, buy them directly (don’t make employees spend their own money and then file for reimbursement).
    5) If you have to make changes that affect your employee(s) be upfront and as clear as possible. “Law Such-and-Such goes into effect next January, requiring us to change our provided health coverage to X, which means that unfortunately your copay is going to increase by Y amount” is much better than “Oh, your copay increased last week? Yeah, it’s supposed to.” (Best is “…your copay is going to increase by Y amount, so we are raising your salary by Z to compensate.”)
    6) Don’t expect your employees to compensate for business shortfalls. “We didn’t get Big Contract, so you won’t be getting paid this month” is NOT a good approach.

  102. Signel*

    Understand the real cost of running your business. I worked at a nonprofit that didn’t buy office supplies (“We don’t have the money!”). They would expect me to print and mail 1,000 letters using my own paper and stamps (seriously!). They used to brag that their only overhead was a phone line. This isn’t realistic.

    1. Anonymouse*

      Seconded. Don’t be a cheapo. When you’re skimping on necessary business expenses, your employees AND clients will notice. There’s a difference between being frugal (mandating travel be economy class) and being CHEAP.

      Director at Toxic Former Job made a HUGE stink about how postage for postcard sized mail adds up for a mandatory mailing campaign that he thought of. Made me mail a 20 page legal document in a regular letter envelop w a forever stamp. I showed him that there’s no way in hell a 20 page document could be folded in thirds– he made me reprint all 400 copies of the legal document double sided to try it again.

    2. Steph*

      Yesssss! At a recent job they didn’t want to pay a small annual cost for a database, and instead they ended up paying hundreds more to have me do an outdated workaround that took a week every year. I have had SO many moments at small businesses where I’ve wondered if they’ve even done the math.

  103. KR*

    Don’t scrimp on basic business expenses and tools to do the job. Do basic repairs on your property. I remember working for a small locally owned coffee shop. As many coffee shops do we kept our stock below the prep counter, however the owners never bothered to get shelves to put our supplies on (cups, lids, bags of coffee, creamer). It was against regulations to have these boxes on the floor (you can’t mop under them, the boxes get wet, ect) so before we had our inspection every year we would put them in a store room and then put them back. The owners decided they wanted to serve espresso but instead of buying a proper espresso machine they bought a Nespresso machine (which does not work at all for a coffee shop setting). The heat didn’t work in part of our work area and they basically told us too bad, wear your winter coats. Didn’t get the ice machine professionally serviced like you’re supposed to, told us to just clean it and not worry about it. Basically what I’m getting at is for God’s sake, if you’re going to open a business don’t cheap out. Spring for the $300 one time expense in shelves so your employees don’t have to creatively tape boxes together for makeshift shelves. Buy the correct equipment that’s meant for industrial use, not personal use. When your employee asks you for tape, pens, whatever just get it because even though it’s a small thing to you those are the things that make a difference to your employees. Pay attention to OSHA and regulations – even if what you have to do by law seems expensive or only meant for big businesses or silly for your small business the rules are there for a reason. Don’t half ass it if you’re going to be a small business owner.

  104. Anon Here*

    I’ve worked for a lot of small businesses. Out of the ones I’ve seen, a good chunk were owned by someone who did not rely on it as a primary source of income to pay their basic bills. People supported by someone else were over-represented. There were people who made almost enough to retire and then left to open a more fun business, people who had inherited money, people whose spouse had a higher paying job – scenarios like that.

    A lot of the dysfunction that I witnessed seemed related to a lack of understanding that the employees relied on this to pay their rent and utilities and buy groceries. In addition to the lack of boundaries, there was a lot of asking people to be on call without pay (“Please be available on Saturday and Sunday in case we need you. If you’re not, we’ll have to let you go.”), firing people for no reason and without any feedback beforehand, “forgetting” to pay people (on time or at all), cutting people’s hours at the last minute without pay, etc.

    In other words, some small business dysfunction has to do with the fact that the business is basically a hobby for the owner and they forget what it’s like to be on the employee side of things.

    I say this to point out:

    If this is not you, you have a better chance of avoiding dysfunction. If you follow basic labor laws and treat people the way you want to be treated, don’t stress about it too much. You can always ask employees for feedback and get better at it as time goes on.

  105. Senor Montoya*

    I last worked for tiny/small businesses back in the late 1970s, but I suspect what I experienced is still pertinent:

    1. Don’t be a crook. If you’re a crook, don’t expect your employees to go along with your need to lie, cheat, and commit fraud. (first job out of college. A real education in so many ways.)
    2. Classify your employees correctly and legally, and don’t lie or misrepresent how you’re classifying them to the employee. (First job again. The IRS informed me that I hadn’t paid taxes owed as an independent contractor. That’s when I found out I hadn’t been an employee. They audited me because they’d been auditing my former boss, the crook. They waived the fine and set up a payment plan, so I have warm fuzzies for the IRS still.) This is where an HR consultant/firm can help you — hours, wages, exempt/not exempt/contractor, etc.
    3. If you ask your employees to take on tasks/responsibilities you didn’t originally hire them for, be willing to hear them say “no” or “I gave this a try and I really do not like doing it, please don’t ask me to keep doing it”. (Third job, they were awesome)
    4. Treat everyone who works at your business with respect and dignity, from the bosses down to the janitor (Second job, they were awesome).
    5. When your employees go above and beyond, or pitch in during peak times, or go along with unavoidable inconveniences, recognize them appropriately and do everything you can to avoid needing to make that ask. (Third job, it split off from second job and I got poached to go with them — akin to a start up. We spent six weeks with our desks in the warehouse while the offices were expanded and made usable. I have fond memories of that, actually, even though it was summer and suuuuper hot. The bosses had their desks out there too, even though they could have worked from home — that made a really big difference)

  106. Lalaith*

    I work for a small company (<20 employees) which is actually not dysfunctional, but there are still things that I wish were done differently.

    As your company gets larger, *delegate*. Don't make anyone (including yourself) indispensable, or the one and only decision-maker or Knower of Things. In this company we basically all report to the CEO, and he has to know everything that's going on and often is the one to tell us what to do or how to respond in certain situations. But he's often out of the office, and though he can often be reached other ways, sometimes he can't, and I don't know when I'll get a reply. Also this means that he can never truly disconnect because there's no one to step in for him.

    As much as you can, try to duplicate or cross-train on positions. We have one position that only one person has the skills for, and when the previous person in that position quit, we went months without anyone who could work on that part of our product. I am one of two people in my customer-facing role, and the other one is on vacation for two weeks right now. If anything happened to me, I don't know what they'd do. In fact, my foot is bothering me today, but I still hoofed it in (commuting via public transportation) because there aren't other options.

    Document institutional knowledge, and keep it up to date. This is really related to my first point, but even if there isn't just one Knower of Things, often you end up with one person having specialized knowledge because that was their area or their project, and then if anything happens to that one person that knowledge is lost. So document it all!

  107. Hedgehug*

    Ok, well, I worked for one small business, and the biggest issue (there were A LOT) was small businesses like to think “we’re a family!” which breeds an infestation of inappropriate, casual, privacy-invading behaviour. I’m talking like, the most dysfunctional Thanksgiving dinner you can picture, because “it’s better to let everything out and hash out issues right away” mentality. Because it’s small, you as the owner, are also HR. But your few employees want to be friends with you, too. Set very clear and defined and strong boundaries. Do not let employees come to you to gossip about other employees. Shut down inappropriate behaviour right away.
    Ok, but here is the other thing you need to learn to navigate. Because you are the owner of a small business, and you are HR, what if your employee has a legitimate issue with you? How can they bring it up without fear of being fired? Ideally, they won’t have any issues with you, but try to be very aware and mindful of potential problems. Stay professional. Know the labour laws.
    I have been away from the small business I worked at for 3 years now, and I STILL have recurring anxiety from time to time regarding my duration there.

    1. JJ Bittenbinder*

      Ugh, you just gave me a major flashback to the tiny firm I mentioned elsewhere. One time, we had a very important client meeting and one of my coworkers well and truly messed up on the reports we were to bring with us and on how she handled rectifying that. While clearly she had some responsibility there, what was a billion times worse was that, after the meeting was over, our boss gathered us all to debrief and made us “go around the room and tell Shay how you feel about what she did today.”

      I need to go get an antacid or lie down or something. Horrible place to work.

      1. Hedgehug*

        omg, right? It’s like living on the set of The Office without the camera to stare into over someone’s shoulder.
        The small business I mentioned above that I worked at was owned by 2 siblings who HATED each other, would regularly shriek, curse and scream at each other, literally with me in the middle between them, regular threats of firing people, constantly changing procedures, etc. This atrocious behaviour would lead to staff also acting like raging siblings during times of stress and pressure. Fun fun fun!!!

  108. Gabrielle Schiavo*

    I used to work with a world economist who was a one-man operation out of his home. I really liked working with him, but his wife was incredibly passive-aggressive and snarky towards me. One example – they had a phone system where you could intercom within the house and my boss told me to change the names on all the phones from the old admin to my name. A few days later the wife was absolutely freaking and my boss told me that she felt “personally violated” that I had gone into the bedroom to change the phone. I explained to my boss that firstly, the old admin gave me a tour of EVERY room in the house and secondly that no one had ever said that those areas were off-limits. Another example was that I’m a helper by nature and I’m a good 40 years younger than them so I would jump in and help them carry things. Next thing I know, I’m being accused of trying to “usurp” the wife and trying to make her feel old. Fine b, I’ll let your 80 year old legs lug your 50 lb suitcase up three levels of stairs next time.

    The wife went on a 10-day trip and both my boss and I were visibly more relaxed! I’ll never work in a married couple’s home again!

  109. Anonymouse*

    Boundaries, boundaries, boundaries. Respect that your employees have rights (legal and contractual). Mean what you say. Have realistic expectations about the employer-employee relationship: you pay them for their work, they do not owe you their lives, careers, loyalty. Ask yourself if you were the most entry level employee at a workplace, how would you like to be treated by the management. Management should take responsibility when something goes awry; focus on solution finding not blame assignment.

  110. Coverage Associate*

    Understand that your technology will have to be upgraded periodically. Even if yours is not a technology heavy industry, even phone systems need upgrades. Give your employees the quality tools they need.

    1. Pay No Attention To The Man Behind The Curtain*

      This is a really good one. Pretty much everything (not just technology) will need to be upgraded periodically — have a plan for it and don’t act like employees are greedy or unreasonable if they want a functional, comfortable chair or a stapler that works. Lifespan of an office chair is about 7-8 years.

  111. DaniCalifornia*

    I’m sure this has been posted about but the family mentality of small offices SUCKS. Our office is 10 people. They all talk about how they are family. Bc they are. There’s the owner. Then their spouse who works during busy season. Spouse’s sibling works here. My supervisor has been here over 2 decades, they brought on a professional who was a family friend. Supervisor brought on their child (who sucks at job.) I am one of few hires that didn’t “know someone” Even the latest new hire of over 2 years has become BFF with supervisor. So yeah the nepotism runs strongly, and the family arguments run even stronger. It’s super annoying to be in the middle of. I hope to never work for such a small business ever again! I am giving notice next week without another job lined up bc it has gotten so toxic due to the “we’re like faaaammily” mentality. Yes…a very dysfunctional family. No boundaries along with passive aggressiveness. No HR, everyone talks about things behind others back, no clear directions.

    The owner also won’t ever tell us what they want until they get super annoyed and then has us make a change. Sometimes it’s something we think is dumb but it doesn’t cause an issue and owner just wants a shelf to look a certain way. No problem with me, they are the owner. Other times it’s from a complete lack of understanding or knowledge of what we do and owner will ask for a process change and dig in when we gently push back on why that won’t work. I don’t expect the owner to know how to do every part of my job, but they just want to change things without ever having done my job and not understanding the processes we have in place. Owner has serious control issues over dumb stuff.

    Honestly, the other major bad thing about small business is the lack of benefits. I have been at my job the same time as my spouse and they now have almost 6 weeks of PTO after 8 years. I started at 2 (with technically unlimited sick days but you weren’t allowed to abuse that, can’t be sick 6 months of the year) and owner bumped everyone up to 3 weeks PTO to cover all vacay+sick 2 years ago. Normally I wouldn’t mind 3 weeks. But we work in a field where 6 months out of the year we cannot take vacation and really shouldn’t be sick, and are working 70+ hours/7 days a week. So of course we are run ragged end of busy season and mini busy season. And I end up sick. More of my PTO goes to sick than vacation. Meanwhile owner takes anywhere from 6-9 weeks of vacation for the entire year. And they work from home every chance they get but don’t offer us the same. Besides PTO they do cover medical ins for employee only but it’s such a HD crappy plan (bc it’s expensive!) that I use my spouse’s benefits instead. No 401k, no other kind of insurannce offered, professional growth opportunities, no trainings or CPE provided. I understand that as a small biz owner things are way more expensive. But if you can let your employees have more flexibility and/or PTO in lieu of offering those extra things it would be better.

  112. Teapot project manager*

    I’ve never worked for a small business but my husband owned one he built up for over 25 years until he sold it 2 years ago.

    Some advice:
    Keep your personal finances completely separate from business

    If you don’t have the knowledge to do the books properly hire someone. He had an accountant, then when we got married I did the bookkeeping (finance background) and then gave the reports to our tax professional each year. When we first got married he only had 1 or 2 employees I did payroll using quickbooks until we transferred that function to an accountant the year before he sold. At that time he was at about 15 employees. We were going to transfer the rest of the bookkeeping such as paying bills to the accountant but then got the offer to sell the business. One thing if you outsource the finances is to make sure it’s someone you trust keep an eye on it and audit the bank accounts. My cousin had a small business and he always did his own books, drilled into him by his dad who did the same. One of his nephews is a dentist who had two separate bookkeepers embezzle hundreds of thousands dollars until one of his sisters who runs her own businesses took over his books.

    Have an employee handbook with clear policies. Have it reviewed by an expert or work with an expert to produce it.

    Treat your employees with respect and treat them fairly.

    Make sure you get all licenses, insurance etc needed for your locality.

    Be sure you have financing for your business. There likely will be slow times. His business was seasonal, we had to expect that for 3 months of the year he didn’t take any money out of the business. For first 3 months of the year all money went to rent, insurance, payroll and other expenses so he could keep employees on and then when it got busy he had a trained workforce and they were able to make money overall for the year, but we had to plan to make it work.

  113. Marlene*

    Know your laws. A small coffee shop was slated to open in my town and they posted a job opening and stated a salary well below the state minimum wage.

  114. Kaitlyn*

    I’ve worked for a few small organizations – one-woman film production companies, a restaurant run by a couple, a two-person charity, etc- and here’s my two cents:

    1. Pay them on time, every time. If they’re an employee and not a contractor, do their payroll properly. Deduct the right taxes, provide them with a pay stub, and have that cheque waiting for them on payday.
    2. Let them see you doing the work. One of the more dysfunctional places I worked, I was the sole admin for an ED, and he was either in his office with his feet up, or out “meeting with donors.” I very rarely saw him doing actual worrrrrk, and when he did, it was always late, fretful, and panicky, and required me to step in and help.
    3. Be consummately professional. Do not overshare about your life, do not ask overly personal questions, use a professional tone in communications, say good morning and good night. Do not treat them like a confidant or a family member or a house elf.
    4. Be clear with yourself about why you’re hiring them. Are they bringing skills you don’t have to the table? Respect those skills. Are they taking some of your workload? Be clear about what each of you owns. Even when you have an employee that is clearly junior, they will bring something that you don’t have, even if it’s an extra set of hands or timetable relief. Respect that they’re bringing it.
    5. Give as much autonomy as possible. Let them work the store alone, or work from home, or run their own calendars, when you can. When you schedule meetings, keep them. If you’ve handed them a project, don’t micromanage.
    6. Be scrupulous about respecting their time off and their OOO time. If you’re like most solo shops, you work all day long. Don’t ask or expect them to, and be very clear when you need the extra mile.
    7. Be an attentive boss – celebrate work anniversaries, get them a good office chair, take them out for a business lunch a couple times a year, do annual reviews and/or COLA raises, send them PD opportunities and offer to pay for them.

    Good luck!

  115. Marny*

    Before you start posting job openings, figure out whether you actually need someone, how many hours you need them for, and what that actual role will be. My husband has interviewed in the past with several small businesses that would describe the job as one thing in their ad (full-time, sales) depict it a bit differently in the interview (sales plus customer service) then offer him a job that’s completely different hours and duties they described (part-time and only customer service) and then ultimately decide they don’t need to hire someone after all. If it had just been one company, I’d think it was a fluke, but this has literally happened to him 3 times.

  116. Snuck*

    I haven’t had time to read all the comments yet, but thought I’d toss my own few in… After many many years working in large corporates I left the Dilbert-esque security/nightmare and instead married into what can only be described as a small business (spread across a large area, with single operators at each location, limited ability to oversight, financially strong, about 6 employees who are not family).

    I’d say, in no specific order:
    Know your own dynamics – if you are a people pleaser, or a conflict avoider, or a detail diver, or a marketing avoider etc… whatever and whomever you are is going to be magnified in the business – a larger business has more staff to share the load, and all the different personalities blend, when it’s only one person in charge their personality traits shine through. If you are a conflict avoider, know this, hire accordingly… be very careful your generous nature isn’t taken advantage of etc. Assume whatever you are will become a key part of how your business will run, and plan for the outcomes of that.

    Hiring choices – think carefully about what you want in the positions around you – you don’t want all yes people, but you also don’t want strident arguments daily. In a small business this would be exhausting and unproductive. Be very clear with people their skill sets are going to need to cover a wide range of problems that come up, this isn’t a many person team where everyone just works on the same widget, but a small dynamic flexible group. If they can’t do that… they won’t fit in. Our maintenance person could just as easily be working on installing new steel plate one day, or driving something 1,000km the next day, or sweeping out someone else’s shed and taking on their customers.

    Finances – Make careful, detailed business plans. Plan out your finances before you start hiring, and make sure the numbers are REALLY there. Don’t ask people to risk their homes, their family’s futures, for your whim. If you are running into financial strife make sure you pay THEM before you pay yourself, and do not live a grand lifestyle at their expense. Remember that if you pay peanuts, you get monkeys – employ qualified, capable and strongly recommended people (ring references please!) and pay them accordingly. The cost of employing them will be far less than the cost of employing someone incompetent, and they will bring in more business for you. Be careful about who has the keys to your money – by all means employ a competent book keeper and accounts person, but make sure you oversight what they do. Learn employment law, and make sure your business people are following the rules for superannuation, taxes and wages – ultimately YOU will be held responsible for this, so make sure that it’s transparent and happening. If you have a large cash flow then I would recommend having a separate bank account for cash, and one for operating expenses so that your income isn’t all in one bucket – reclaiming money that’s stolen from a business is slow and can see a collapse of the business.

    People – I’ve already said hire competent and qualified… but also hire decent people. People who are inherently kind and have reasonable ethics. Then you can throw a few juniors in, and they won’t be abused. Hire staff you know you can trust, as you’ll be so busy yourself you can’t micro manage people, especially in start up stages where there’s a lot to do and not a lot of people. Hiring isn’t just about qualifications, there’s people skill qualifications too – soft skills. Look for integrity, honesty, work ethic and a willingness to be flexible and share their knowledge. As you expand you will take on people with different skills and you really need a team mindset while the team is small.

    Your mindset – you need to remain humble, you need to remain transparent. You don’t need to share every book keeping report, or tell everyone how profitable your business is (I’d advise against this!) but you can say “We’ve had a good quarter, and if next quarter is like this there’s a chance we’ll get more staff in” or whatever. Likewise “This quarter has been a little lower than I’d have liked, I’m hoping we can turn it around” is sufficient. If staff are annoying you don’t go home and quibble to your wife but do nothing about it, likewise dont’ talk to the other staff… you will need to quietly pull that person aside and ask for the changed behaviour. Small teams can’t handle disquiet with problems. Likewise problems between your staff – weigh them carefully, hear both sides, don’t pick favourites, and consider the wider reliability and what you know of both parties before making a decision. Your job isn’t to be ‘judge’, it is to get everyone working effectively. They aren’t children, expect them to be adults…. On the humble front… showing up in a Mercedes while everyone is earning minimum wage doesn’t work. Driving a current model Range Rover when you have a farmer’s back and do 100,000km a year isn’t an offence… think through not just what message you are sending your customers, but also your staff.

    Time – put aside a chunk of time each day to actually manage. You might be very busy finding new clients and managing finances etc… but if you don’t actually manage… you wont’ get what you want. Hiring the right people can help with this, but you still need to make a concerted effort to check in with them, not while you handle other phone calls or think about your BAS statements, but actually put work aside and check in with them. Not a lot of time for good quality staff, but enough to ensure that everyone is in the same boat, moving in the same direction together.

    Resources – keep track of them. Cars, computers, phones, water tanks, cranes, generators, MIG welding gear, hardware store accounts, fuel accounts etc has all been considered “flexible ownership” at some stage by our staff. You’d be VERY surprised what people think they are entitled to when they are working long hours or have been with you for a long time or feel they are doing you a favour by their mere presence. This isn’t ‘watch everyone like a hawk’ but more ‘lay out clear expectations of how resources are to be used up front’ and then only manage if that isn’t how it’s used. (And if you ever see one of your cranes tootling down the highway on a Sunday morning in the middle of no where… have your phone charged and ready to ask for an explanation!). Also you can reward good staff very easily with these resources – sure you can have a crane to lift some trees on your property… or cover someone’s phone bills (or supply them a phone) or internet… etc. Those costs can be taken against the company and cost you less, but rewards the staff member considerably too. Just be mindful of who keeps the telephone number when they leave – if it’s a sales position you probably want to issue your own number and retain it when they leave. It’s a nice bonus to give to high performing staff that isnt’ huge.

  117. nnn*

    Another thought:

    Be clear (first in your own mind, and then with your employee) about what your business’s values and priorities actually are, regardless of what you say in marketing copy.

    For example, don’t say that your priority is customer experience when what you actually need your employee to do is upsell.

    This can be hard – maybe you want to think of yourself as a company that prioritizes customer experience, maybe your ego is tied up in that. But if the fact of the matter is you need to make rent at the end of the month, you need to actually tell your employee that.

  118. SS Express*

    I’ve worked in a few different (very) small businesses, and one common issue is doing things that just don’t make a lot of business sense or aren’t very “professional”. Smaller businesses usually won’t have the same processes as larger ones, don’t have multiple levels of management which means there’s nobody to push back on bad ideas, and are run (and sometimes staffed) by people who are highly invested emotionally and therefore sometimes struggle to be objective. On top of that, the longer someone has been running their own business away from the rest of the corporate world, the more likely it is that they’ll fall out of touch with professional norms.

    If I was to take a job at a small business again, I’d be looking for evidence that the owner was business-savvy and in touch with professional norms: not having weird/dated/illegal requirements like asking me to submit a handwritten cover letter so he could check my handwriting was good, having a clear vision for the business that’s based on actual knowledge and data, being familiar with whatever trends/technology/products are relevant to that industry, outsourcing things that require specialised skills instead of DIY-ing stuff like graphic design, and not cutting corners in ways that are clearly going to lose the business more money than they save. And of course, treating the recruitment process like a two-way street and never saying the F-word (family).

    1. 1234*

      I’m echoing your sentiments about weird/dated/illegal requirements. At one of my small business jobs, I found an old company manual that required employees to let the company know if they engage in “strenuous sports!” Like which sports do you consider strenuous? So what if I wanted to train for a marathon? I don’t have any obligation to disclose that?

      YES OMG to the “DIYing graphic design” I suggested to my boss that we will need a graphic designer for XYZ project you wanted me to take on/update. I get back as a response, “well, how much does it cost if we just buy Photoshop ourselves?” *facepalm*

      1. Gazebo Slayer*

        Maybe it was some sort of worker’s compensation or insurance thing? Sometimes people try to claim worker’s comp fraudulently for injuries from sports or home projects or whatever.

  119. VeryAnon*


    * Don’t lie about pay, raises or responsibilities.
    * Don’t bait and switch the role.
    * Don’t overshare your personal problems.
    * Don’t make your employees into your free counsellors.
    * Don’t treat employees like idiots.
    * Don’t treat your employees like friends.
    * Don’t flaunt your wealth, especially when pretending you ‘can’t afford’ raises. Be upfront that you just don’t want to pay that person more.

  120. Pet the Cat*

    I work for a small business (I’m at my desk here as we speak) and it is exhausting. I miss having policies and procedures. I miss HR. This is the first time I’ve worked for a small company, before it was always massive corporations (a state university and a contractor for a power plant). My boss is so emotionally invested in everything and everyone, which is laudable to a point, but he takes it as a personal insult when someone else isn’t as invested as he is (i.e. taking a job elsewhere). I mean he genuinely gets his feelings HURT. We have had multiple discussions (at his insistence) about why women dress inappropriately (I’m a woman, btw), about how trans people don’t exist (I shut that conversation down hard), and how sleeping around is the worst thing you can do as a person (what the actual fuck?). He has screaming matches with other staff members when they don’t ask his permission to do something/don’t do it the way he would, but he complains that everyone keeps calling him with questions and no one can do anything on their own. His wife does the accounting, and one of his sons works here, and they pad his timesheet whenever he’s under 40 hours. I’m only planning on staying here long enough to make my resume worthwhile (I was fired from my last job for some attendance issues, so I feel like I need to give it some time here before moving on), but I have 100% checked out. I feel bad that the level of shit that I give is so non-existent, but…not bad enough to start caring.

  121. Beth*

    Don’t use the smallness of the business as an excuse for it being a lousy job. In particular:

    If you want good employees, pay them well and value them. As your business does better, PAY THEM BETTER.

    If you can’t afford decent benefits, find something that your employees actually value and offer that as a token of appreciation. And DO NOT let that excuse you from adding benefits as soon as you possibly can.

    You want the kind of employees who will help you make your tiny business into a larger and more successful business, right? You can’t have that unless you make it worth their effort. If you don’t value them as you should, you don’t deserve the kind of employees who will help your business succeed, and you won’t get them.

    Instead, you’ll get mediocre employees. In fact, you just might get really good employees who then turn into mediocre employees, because that’s what happens in toxic workplaces.

  122. Steph*

    Honestly, as someone who’s worked (and works) for multiple small businesses, a lot of the dysfunction comes down to the fact that the employer doesn’t believe labor laws apply to them because they’re “so small” or “running a small business is so hard” or “that would be be too much ($$, time, etc.) for us because we’re so small”, and that provides some kind of license for ignoring industry (or cultural or just general) standards for how to treat employees. A lot of small business owners I’ve worked for have hired people they think are desperate for the work and then want their employees to be so grateful for it that they’ll excuse anything. Like someone else said above, if I was going to work for another small business I’d want to see my boss/the owner was in touch with industry standards and didn’t live and work in an isolated silo.

    Also, don’t try to or claim to treat your employees like a family. This is a huge red flag to me now based on previous work experiences and no solid, talented potential employees out there are looking to be treated like a child or cousin – we’re looking for reasonable supervisors and interesting work that uses or develops our skills. We’re not going to be happy being told to do something the long or inefficient way just because that’s what our boss is comfortable with and has always done because they’ve had the ability to only surround themselves with people who will bend to that, for their entire career.

  123. Adhara (UK)*

    I’ve only really worked in small retail businesses, so what’s acceptable to me can be a bit warped.

    Adding to the “don’t make employees wear too many hats”, I’m gonna add that owners shouldn’t as well. My current boss(es) are adamant that they have to handle all of the purchasing, most of the finances and also do the back end paperwork and social media fun stuff. And they keep all of it secret, so when they wear one hat, it’s a pita getting any other hat on for one question answered.

    Eg I found out they get a lovely spreadsheet from the supplier on what items will turn up when. Gee, wouldn’t the sales team love to know this too, so we can tell customers “it’s been ordered, and it will turn up on x date”. Not our current system of “it’s been ordered, and it might turn up on x date? We won’t know til it arrives”. (Also, because of the many hats they are not obsessively butt-retentive about stock levels and we run out of xyz on a frequent basis, with a new shipment coming in in 2 months time. Re-order reports, what are they???)

    Basically if you think that wouldn’t fly in a bigger business, it’s likely that you shouldn’t do it in a small business.

  124. ZucchiniBikini*

    My perspective on this is as a one-person microbusiness (I’m a freelancer who works for several higher ed and government clients) who uses subcontractors periodically to manage workload. My subbies are not employees and don’t have an expectation of regular work from me, and nor do they get any benefits. The rules I set for myself before I first engaged any subcontract labour were these:

    – Pay people not just decently, but well; pay on time; and do not haggle over small stuff. I went against business advice and set rates for my subbies at between 70% and 90% of my own hourly rate, despite that meaning that I really don’t make much on the hours of theirs I bill my clients for (sometimes nothing, once you factor in the quality checking and admin). For me, paying people well and keeping my clients satisfied by being able to consistently meet their challenging deadlines was more important than squeezing every last cent. And I think it’s paid off, not just because I feel ethically comfortable with it – my subbies are high quality, stable, and always keen to take my work.

    – Be clear with the work description / brief, be responsive and supportive, give appropriate and realistic deadlines, and respect people’s non-working time. I saw a few subbie / employee relationships in friends’ businesses fall apart because the business owner was too vague in their description of the task or role, or left the person to get on with it without assistance or advice, or continually set unrealistic deadlines, or thought it was OK to ping their subbie at
    10pm on a Friday or 10am on a Sunday without prior notice.

    Some of the things I’ve seen above as must-dos and must-nots from others are actually the opposite of my experience. I use three subbies, one of whom’s my best friend and one of whom’s my daughter … and it works. Because I bill as sole trading freelancer and am paid into a joint personal account, my business income is entirely commingled with my household income … and it works (according to my accountant, remarkably well – I do keep meticulous records, but I have never had any difficulty with tax etc). I do have one policy that I wrote which all my subbies agree to, which covers client confidentiality, respectful behaviours, and my obligations to them, but I don’t have a big raft of policies … and so far, that works too, but I’d be open to developing more if more are needed.

    There are a lot of things about the way I do things that wouldn’t work in a larger business, or wouldn’t work even if I had employees rather than used subcontractors (the distinction between the two, in Australia where I am, is very sharp at law). But for my microbusiness, these methods do work. And I have no interest in growing my business any larger. It already provides me with a very good income and a highly flexible work life, which is all I wanted.

  125. Retail Woes*

    Listen to your employees! It’s likely your employees will know more about the day to day operations than you might see, so it benefits you as the owner to hear them out when they have concerns.

    I used to work for several small retail businesses and at a few of them the owners had no idea what the daily status of the store was! They had their own ideas about “what customers want” and refused to listen when employees said certain products weren’t selling, or they’d ignore feedback about how well certain practices were working. Probably the most annoying part was when the store would be open on a bad weather or otherwise slow day, staffed with too many employees than needed, and refused to send some people home and/or close the store early. The infuriating part was the next day when they’d get upset at the employees that sales were down and that we didn’t break even for the day!

  126. Letter Writer - Katie*

    Thanks so much to everyone for the thoughtful responses. Some were reassuring and some very illuminating. A few gems in there that I hadn’t thought of! Sorry I couldn’t be in the conversation on Thursday – life stuff was happening. It’s so great to get all your input though, and I will be bookmarking this to re-read and reconsider when I start making more steps towards my first hire. I’ll be sure to send in an update when I have one!

  127. Dust Bunny*

    Agreed with everyone who says that “we’re family” is a red flag. I’m not in close contact with a lot of my family for Reasons. What I hear when you tell me a workplace is “like family” is that you don’t respect boundaries, expect me to spend time and do favors without adequate compensation; you will very definitely play favorites, including keeping on a lot of dead weight because They’re Family; and you’ll expect me to put up with a lot of drama and shenanigans because They’re Family. I don’t want to deal with all that from my actual family so I definitely don’t want to deal with it at work. My last small business job couldn’t give me the raise I’d been promised when I was hired because the owners gave away so much make-work employment to useless friends and relatives.

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