should I work for a tiny organization?

A reader writes:

My husband works in the public school system (not a teacher) and is considering a job offer with a one-person nonprofit. He and the CEO will be the only employees aside from volunteers.

He’d be working virtually and he hasn’t negotiated the offer yet, but I thought I’d ask you and your whipsmart readers what important things we should consider before making this kind of move (things to worry about/ask in advance, generally how to set this up to be successful if he decides to take it).

How well does he know the CEO?

Unless he knows the CEO very well and knows her to be sane, reasonable, and very competent — or unless he knows others who have worked closely with her and will attest to those things (and they should be people whose opinions he respects) — I would proceed with extreme caution.

If the CEO is indeed sane, reasonable, and very competent, this could be fine. Truly — I know people who have had great experiences doing exactly what you’re describing, because the CEO was excellent.

But if she’s not all three of those things, the chances are high that this will be unpleasant and frustrating.

When you’re working with only one other person, and especially when that person is your boss, they have an outsized impact on your day to day quality of life at work. The impact of incompetence or craziness isn’t as contained, and there aren’t any other perspectives in the mix — no HR, no senior-level directors, no one else to provide oversight or a counter-balance against ideas or habits that can range from mildly annoying to outrageously terrible. In a two-person organization, that other person is going to loom a lot larger in your work life than if you had lots of colleagues.

If your husband moves forward with exploring this, I’d encourage him to do three things:

One, he should thoroughly interview his would-be boss. Don’t just ask a few questions about management style — spend serious time digging into how the person works, how she manages, what the goals are for the organization and for your husband’s potential role, the plans for meeting those goals (and be rigorous about evaluating those plans), how she’s addressed obstacles that have come up in her and others’ work in the past, how she describes the work culture she’s striving for, and what has worked well for her with past employees and what hasn’t worked well. He should also ask questions about the stability of the organization and his position there. What would happen to the organization, and his job, if she decided to move on from it? What funding is already in place for his position, and for how long?

It is very reasonable to dig in this deeply when you’re contemplating joining a two-person organization, and she should welcome it as a way to make they’re aligned. If she doesn’t welcome it, that’s a danger sign.

Two, he should talk with a range of people who have worked with the CEO before. He can ask her to put him in touch with people who can talk with him about their experience working with her. That’s not something you’d normally do if you were interviewing at a larger organization, but again, with a two-person organization, she should respect this request and be glad to accommodate it. If she doesn’t, that’s a red flag too. (He can also do his own sleuthing using LinkedIn, but it’s okay for him to be up-front with her that he’s seeking to talk to people who have worked with her before.)

Three, he should approach this with a genuine spirit of investigation. So often people decide they want the job first, then do this kind of due diligence half-heartedly because they’ve already made up their mind. Deciding that you definitely want the job before you do steps one and two above make it really likely that you’ll miss or ignore serious danger signs. There’s plenty of time to decide that you want the job and to get excited about it after doing these steps, and approaching it that way will give you a much better outcome.

{ 108 comments… read them below }

  1. Not Today Satan*

    I agree with what you said, but I’d also add that (and this may be obvious) networking/relationship building will be a lot harder. If he chooses to leave, there’d be no one at his current place of employment who could be a reference (or who could put in a good word, etc.). There’s also essentially no ladder to climb within the organization.

    1. Nea*

      There’s no ladder to climb, but when you’re the only employee it’s surprisingly easy to cross-train on a lot of new skills because there’s no one else to jump in and do them first. That was my experience.

      Unfortunately, my other experience was as Alison said – my boss did not fit all three of the requirements.

    2. Specialk9*

      Agree with the first point, but for the second, getting in on the ground floor like this makes the ladder irrelevent. People who co-found a group often end up VPs or such, when otherwise they might make a manager some day. And once you are a VP/etc it’s much easier to move sideways into a similar position at a bigger org.

      1. Manders*

        Yes, sometimes at a small company, you’re sort of building the ladder underneath you rather than climbing it, and that’s an awesome experience. But other times, at small places with no rules about nepotism or no consequences for favoritism, you might find that as the organization expands you’re dealing with more potential for conflict with people you don’t have the authority to discipline.

        I still love working for small businesses, but I now hold very strictly to the rule that I won’t work in any reporting structure that involves two members of the same immediate family if the business is too small to have an HR department. Husband/wife or parent/child teams can get very toxic very quickly for coworkers outside the family.

        1. GreyjoyGardens*

          I agree with this policy regarding small businesses staffed by a spouse or parent/child team. Been there, done that, got the T-shirt, 0/10 do not recommend. In my experience, husband/wife or parent/child teams are either 1) way too enmeshed, or 2) one person, usually but not always the child, is there because they are so toxic that no-one else will hire them.

          I’ve learned to run far far away from small “family” businesses staffed by multiple family members. It’s not the “small,” it’s the “family.”

          1. GeekyDuck*

            Mr Duck currently works for a company where in one family:
            -Dad is CEO
            -Mom is President and COO
            -Son is CTO
            -Daughter1 is SVP/She Who Controls Access
            -Son-in-Law2 is HR and CFO

            The only family members not employed by this place are DIL1 and Daughter2. It’s a nightmare and he cannot wait to get the hell out. The enmeshment you mention is most definitely a factor — discussions about who will be at parents’ house for dinner do NOT belong in a sales team meeting, or (warning) the nitty gritty of DIL1’s pregnancy/obstetrician appointment. His biggest problem is that there’s a) no way to discuss problems with an “exec” with anyone, because they’re all related and can’t separate the work day from family life, and b) the only way he could ever get promoted is to marry Daughter1 by the looks of things, and I’d be pretty Not Thrilled about that.

          2. Yes*

            I can’t speak to the other types of family-run businesses, but speaking from experience I totally agree about husband/wife-run businesses. No boundaries, way too enmeshed, too little accountability and zero objectivity.

      2. Not Today Satan*

        I didn’t get the impression this organization was expected to expand. My mom has worked for a 2 employee nonprofit for 20 years.

    3. TCO*

      There might not be an existing ladder to climb, but small non-profits can be really great places to advance/expand your skills because there’s not a dedicated person to do every task that needs doing. Whether or not those increased skills result in an increased salary and title depends on the organization, but at the very least it can help you move up in your next role.

      As for networking, I’d be curious to know how closely this employee will interact with board members, colleagues at other organizations, etc. Those relationships can be helpful for references, career support, and social interaction that OP’s boss might not be able to provide.

  2. Murphy*

    Ask about how volunteers are recruited, trained, etc. There can be a ton of issues with a mostly volunteer staff. (Don’t get me wrong, I love volunteers!) I worked at a very small startup nonprofit once (President and two part-time staff, everyone else volunteers), and the President was really desperate for people. Any warm body was allowed to volunteer, sometimes in big impact roles, with no real training or guidance. Some of them were really unreliable, but the President was willing to take whoever she could get. I worked at another nonprofit that had more staff but relied heavily on volunteers. In that case, they performed very specific tasks and were trained and supervised by staff.

    1. Pine cones huddle*

      Yes! And sometimes if there is no volunteer, then it doesn’t get done. And this is a HUIUUUUGEee problem in some areas. I have interviewed at orgs that were so proud of being volunteer driven, yet their website was embarrassingly out of date because the volunteer who helped them with it has left and no one had updated it in 8+ years. And even that volunteer was only kinda ok and not terribly skilled. So now instead of basic updates if needed a major re-haul and there were no skilled volunteers to do it. And no desire to invest in it since they were sure another volunteer would come along. Doesn’t seem like a big deal, but if your job is in an area that relies on people being able to go to your website for information then good luck! The mentality can get poisonously “lean”.

  3. paul*

    It’d be a hard pass for me, and I say that as someone who’se worked with (not for) a lot of small non-profits. It’s more potential to go sideways than I’m comfortable with, even assuming a fairly rational and decent CEO. Super-small non-profits are notorious for folding quickly, if nothing else. That goes double (hell, triple) if they’re single-source on funding.

    If you do go through with it, assuming they have a board, you *also* need to investigate the hell out of the board; I’ve seen bad boards ruin an organization.

    1. a name*

      I work nonprofits and lying to candidates is a really significant problem. Even if he does his due diligence, the person may just be stringing him along to get him to commit.

      I just had this happen today, a core stipulation of my hire was broken. I’ve had the job six days.

      1. Pine cones huddle*

        Also work in nonprofit and I had an org so eager to hire me that the offered me double what they’d paid the last people in the job and over and over flat out lied about the day to day duties and responsibilities of the job. Needless to say it went horribly and I left after 4 months without another job and I will warn anyone I know who considers a job there (surprise, they have a ton of turnover) #noregrets

  4. Dawn*

    I have never seen a situation like this work out for the best- I’m sorry to be so pessimistic OP, but in every scenario I have ever been in where I was the sole employee and in every scenario I have ever seen play out with friends, colleagues, and strangers on the internet…. it always ends in tears and frustration on both sides.

    When you’re 1:1 with someone day in and day out, and that person is responsible for the whole company, unless that person has iron-clad rock-solid boundaries and can fully (and I mean fully) keep a professional CEO – Employee relationship, all kinds of business weirdness will bleed over and you’ll become the unwilling confidant, therapist, friend, drinking buddy, and/or punching bag. That’s one of the reasons AAM is recommending your husband do such thorough due diligence before working for this individual.

    Please, someone, tell stories of how a situation like this worked out amazingly for all involved! I don’t want to be such a downer :)

    1. K.*

      The biggest “absolutely not” situation I’ve had in my working life so far was being the sole employee. Someone referred me to someone who was looking for a person with my qualifications. The name of the company didn’t indicate that there were only two people – I found that out when I Googled. I got to speak to the outgoing employee and I asked her why she was leaving. She mumbled something about stress and needing a break without looking at me. This was in 2009, so during the recession – quitting without another job lined up was not really done. I met the boss and was IMMEDIATELY like ” … Oh wow, no way.” It would have been tricky under the best of circumstances, but I could tell right off the bat that she would be very, very difficult to work for and there was no buffer around her, so I opted out. Shortest interview I’ve ever had. I don’t think she was crazy about me either, so neither of us saw the need to waste time.

      1. Pine cones huddle*

        I know of an org with 2 employees: the CEO and the [insert title of the month]. I know 2 people who have worked with this CEO and its not recommended. Apparently no one lasts a year before they are fired or just up and quit.

    2. Non-profit veteran*

      I have a success story – I work for a three person (counting myself) company and it’s working really well for me, for this stage in my working life. I went in with my eyes wide open as far as the dysfunctions of my team (they are many, this site would probably be horrified) and the limitations to my career (people upthread who have pointed out challenges with networking, career growth at the company and references are right on.) For me, I knew had great boundaries so was confident I could manage the interpersonal dynamic, and I had worked with both of my team members and liked them fine as people and respected them as professionals. I’m sure you all are skeptical reading this but my boundaries are only stronger two years in.

      Things I did going in: I negotiated a salary and benefits package that made up for the limitations in career growth – my small company pays a large portion of my health insurance, contributes to retirement, and pays for life insurance, all on top of a solid base salary with a bonus structure. I was also really honest with myself about why this job appealed to me. I wanted to have children, my husband is early career in a demanding and inflexible job. I didn’t want to pay for the kind of childcare we’d need for both of us work at that intensity but I also 100% wanted to keep working myself. This job gives me incredible flexibility in hours, I work from home, the hours are not demanding and on the rare occasions they are, I get a bonus for overtime. I am basically working part time for a full time salary.

      Seriously – my company hired me, I got pregnant that month, and they wrote a family leave policy for me with no questions asked and no guilt applied. I took 12 weeks off – we are a consulting firm and bill by the hour – this was an actual hardship for us. My co-workers questioned nothing, and are hoping I will have more kids. I do think it will be pretty hard for me to re-enter the regular workforce later on down the line but for me being able to continue working at all while parenting babies is totally worth it.

    3. J*

      This. I’ve twice worked at smaller non-profits, with different problematic experiences. At one of them my boss tried to be too “buddy, buddy” with myself and the other staff member, to the point where he would ask personal and uncomfortable questions about my love life, among other things. We also would occasionally go out drinking, but since he was an extreme extrovert (and I a very extreme introvert), it was an exhausting experience because he wouldn’t let me leave after just one drink. This was several years ago and I’m better at standing up for myself now, but there was a pretty serious boundary issue.

      At the other job, I was one of six and had a colleague that was difficult to work with, which had a profound effect on my well being, as I was often the target of her wrath.

      1. GreyjoyGardens*

        Ah, the lack of boundaries…IME that is the biggest issue at tiny companies, especially when it’s just you and the boss. I still shudder at the memory of working at a company where it was just the owner, me, and then a part-time freelance graphic designer. Boss wanted a confidante as well as an office manager, so I got to know that her husband refused to have sex with her anymore (what do you say to that?) but she couldn’t divorce him because it was against her religion (really, what do you say to that?). Needless to say, the job ended badly because the boundaries just weren’t there.

        I don’t think all super-small companies are like that but when it’s just you and the boss, or even you, boss and one other person, it can get to be a really “hothouse” atmosphere where you have only each other for company at work, and so little things get on your nerves all the time OR the relationship becomes too buddy-buddy and lacking in boundaries.

    4. Sunshine on a Cloudy Day*

      Actually… and I’ll preface this by saying I’m about as “anti-small-company” as you can get (got severely burned by a working at a tiny, dysfunctional, family owned company – might be an over reaction, but it was so traumatic I’ve said NEVER AGAIN).

      Now that all said – I have a friend (former roommate, so we talked a lot about our day-to-day/work lives) who is the sole employee of a biz owner (not a non-profit, so might be slightly different) and has what I’s consider a success story. He’s been there for about 6 or 7 years, and while it’s not perfect, from what I’ve heard it’s not horrifically toxic/dysfunctional. To me it sounds like an overall decent place to work (maybe not amazing, but definitely nowhere near as bad as some of the horror stories we’ve seen on AAM).

      There are drawbacks – as he considers moving on, it will be a bit harder than usual because his boss is basically his sole reference since school (he had a few service/hospitality jobs, but this is his only “office” type job). In terms of growth – well, he’s absolutely grown his responsibilities. His boss took six weeks off internationally, (basically in the opposite time zone) which left my friend really running the entire company on his own for a fairly impressive length of time. However, it is tough to translate some of that, mainly level of responsibility (vs expansion of types of responsibilities) to very rigid corporate/hierarchy types of people.

      There have been a few minor issues with boundaries/professionalism from the boss. These sorts of issues seem fairly problematic when I hear about them from the friend (I think the biggest issue is that if the behavior does not stop or gets worse, there’s no external recourse, so that makes the original issue seem more troubling), but then when I compare them with what I’ve seen/dealt with in the rest of my career within mid-large size orgs – well friend’s boss is pretty solid. I guess what I’m trying to say is that small issues can seem magnified.

      I’m pretty sure that my friend happened to luck out here – I remember we were job searching at the same time and had compared prospects/methods. We were both pretty young and dumb so I highly doubt he did the kind of diligence Alison is suggesting. He just happened to stumble upon a sole-employee role for a reasonable person, and more importantly that is a very good fit for him in terms of style/expectations.

      I’d say something that seem to contribute to the success in this situation is that this was an established business before my friend was hired. His boss had been operating the business herself for about ten years (or so, I believe), and did have people work for her either temporarily (project based) or part-time, though she never had more than 1 part-timer + 1 project person at a time, but still she had worked with a variety of people in a boss/employee relationship before my friend was hired. He was hired as her first full-time employee.

      1. Breda*

        Your friend & I seem to have very similar stories! It’s worked out pretty well for me, with the caveats that a) I’ve pretty much reached the maximum possible salary here (though there’s room to expand on commission), and b) it can be frustrating to only have one person’s experience and methods to build off – I have to invent things for myself more often than I’d really like to.

        A few things that make it easier: we share an office with another (6-person) business in the same industry, which means it’s not just the two of us day in & day out, and my boss works from home two days a week so we get a break as well. Also, while my boss is extremely loose on boundaries, she’s amenable to my rather more hard-line ones. We also have very compatible senses of humor, which is important!

        Positives: I get a lot of freedom to develop my role the way I want to, and because I do EVERYTHING, I have a great sense of how companies like ours run. But yeah, I lucked out: a friend who was job-searching at the same time landed in a similar role at a three-person company, and her boss was a nightmare to work for. I was a year of part-time work out of college, so I was pretty desperate and had no idea how to do this kind of due diligence. I feel pretty fortunate that it’s been a positive experience!

      2. KellyK*

        I’d say something that seem to contribute to the success in this situation is that this was an established business before my friend was hired. His boss had been operating the business herself for about ten years (or so, I believe), and did have people work for her either temporarily (project based) or part-time, though she never had more than 1 part-timer + 1 project person at a time, but still she had worked with a variety of people in a boss/employee relationship before my friend was hired. He was hired as her first full-time employee.

        I’d expect this to be a *huge* factor. You don’t want to be the guinea pig on whom someone else learns to manage, especially when they don’t have a manager above them to give them any guidance.

    5. Ali G*

      I have a success story! Right out of grad school I took a job with relatively new non-profit where I was the only staff person besides the CEO. I ended up being with that organization for 8.5 years before moving on for new opportunities. I think things worked out for me because:
      My boss/CEO was close to retirement and saw this as a way to go out “on top” by starting the org off right so that it would be successful – and he did that
      We had guaranteed funding through a trade association, so we weren’t high stress about development (this is rare, I get that)
      I was highly motivated and my boss gave me a lot of leeway and responsibility. He traveled a lot and so I had a lot of autonomy on how I structured my time
      We had 2 offices in the office space of a larger non-profit, so I had people my own age around. This helped both for when boss was out of the office and just to have someone else to eat with or talk with other than boss.
      We really just got along and he was a good boss. I learned a lot from him and other skills that have carried through my career.

      1. Chaordic One*

        You were, indeed, very lucky, Ali G. I would really worry about having the funding to support the mission. I would hate for the cost of salaries to eat up all (or most) of the money that the nonprofit raised.

        OTOH, as an employee (even of a nonprofit) you do deserve to be paid fairly for your efforts.

  5. Bea*

    I’ve never worked for a company with more than 20 people total and always work directly with ownership.

    The important part is making sure she’s set up to do business as a business. This means that she’s doing payroll through a service and not classifying him as a 1099 if he’s not truly a contract worker. Or that you are clear what being issued a 1099 will result in.

    I would want proof of financial stability. This would be hard to demand but given the risks I wouldn’t blink twice at it.

    A clear cut description of the plan and how she views growth in the future because if she brings on one employee she hopefully is gauging for another as business picks up.

    I would need to know so much more about her personally because it’s beyond boss and employee when you’re the only one in the boat with the captain.

    I am working at assisting startups so I’m thrilled and less worried about risks in many ways but at the same time, that’s what would be on my agenda in this situation. I’m usually a person someone calls in a few people deep given my expertise.

    How can he grow with the business? Is it something he can eventually get a chunk of because of being #2.

    1. Manders*

      My work history is similar, except for some college/summer jobs. I’ve had some great bosses, some lousy bosses, and a few who were ok but not anything exceptional. The skill set I’m building is very useful for startups, so I’ll probably be working at smallish companies for my entire career.

      In addition to your excellent list of things to check, I’d add:

      – Do you trust this person’s judgment about the tasks they’re hiring you to do? In a small company, there’s no higher authority to appeal to if your boss is telling you to do things you know are wrong. I’ve had times where I had to do ridiculous, unproductive tasks because the boss was wrong about something but very insistent that it had to be done in a certain way.

      – Do you have a “screw you” fund to fall back on if the working relationship doesn’t pan out or the company shuts down suddenly? In such small companies, if the job turns toxic, it’s hard to put your head down and get your work done quietly. It’s also easy to go from “everything looks fine to me” to “we’re closing” very quickly.

      – Does the boss seem clear on how all the little administrative details of having an employee will get handled? If not, do you trust that they’ll be able to make good judgement calls in the moment? I’ve worked at places that didn’t have any formal policies in place for events like bereavement leave.

      – Does the boss seem realistic about how the business will grow, and reasonably capable of dealing with setbacks if it doesn’t? Sometimes you end up with pie-in-the-sky plans that don’t work out, and a good boss should be able to acknowledge that they might not hit those goals.

      1. Bea*

        I gasped because I’ve been so lucky that I’ve never dealt with anyone set in the “this is the only way to do it” mindset before. I have bulldozed into positions my entire career and everyone was like “well damn…that is a more efficient way isn’t it.”

        So yes, that’s absolutely critical. You have to go into this with your own set of ambitions and make sure they jive with the CEO’s. Which is why it’s critical the personalities and talents complement each other. I’m fast to say “I’m not here to cook your books, I’ve spent years scrubbing financials after others have messed them up.” So I’m not going to get along with shady unorganized dysfunction coming out if the gate.

        1. Manders*

          Oof, yes, I think we’re in different fields because I don’t handle anything financial. In that area, you have to be extra capable of standing your ground because your boss’s quirky way of doing things might not just be a poor choice, it might be illegal.

          I did once witness a disaster at a small company where the accountant who had been there for years developed memory issues, then she died unexpectedly, and then the company got audited. It was a mess.

          1. Bea*

            My beloved former boss developed early onset dementia and I had to pry a lot of his long gone memories out of file boxes on my own. I can’t imagine if he was doing anything more than signing checks and looking at financials that I had copious notes on so he understood!

            I’ve been elbow to elbow with grumpy old men my entire life, my grandpa and my uncles (my dad too but I’ve quickly exposed his softness). And then my bosses and long haul truckers. I’m not scared easily and often tread lines when it comes to “that’s the boss tho”. I know. Their best interest is my biggest concern so I’ll tell them to shape up when necessary! That’s part of being dealing with financials and regulatory agencies “no we don’t ef with OSHA, boss.” “ef them!” “yeeeah but still we are following their rules.” kind of stuff.

      2. CG*

        I don’t have much to add to the already useful insights that everyone else has ITT, but I do want to echo Manders’ mention of a “screw you” (or “F off” if you want to go all Billfold about it) fund. Don’t just think about what it’s going to be like for your husband to work for/with one other person, but also think about what it will be like after. Jesmet mentions references below – does your husband have a work history that may make it hard for him to find his next job if he is not comfortable down the road with the CEO finding out that he’s job hunting? Are there networking/client interaction opportunities or will your husband primarily just be working with the CEO? Will he have opportunities to develop a reputation not just pegged to CEO’s, either if CEO harms their own reputation or if their relationship with your husband sours? Per Manders above, are you financially stable enough as a couple that you could handle the ramifications if things go south in this job and hubby needs to leave immediately or is forced out? What would you do if the non-profit’s finances become tight or can’t be smoothed over the year?

        I think especially in an org where you are the only person other than the CEO, it’s helpful to think of the most pessimistic scenario of yourself as the most costly, most disposable person: you cost a regular salary and benefits, as well as closer attention paid to labor rules and management principles, that a solo CEO may otherwise not always consistently worry about for herself alone, and in tight times, a non-profit CEO may decide that some gaps need to be filled with volunteers.

  6. Snark*

    Even rational, reasonable, good-hearted, and decent people are not rational, reasonable, good-hearted, and decent at all times and in all situations. An organization this small and this flat is going to be extraordinarily susceptible to the CEO’s whims, bad decisions, missteps, personal foibles, and whatever.

    1. Snark*

      And, therefore, I do not trust any organization that lacks sufficient critical mass and power diffusion to call bullshit on the chief.

  7. Penny*

    Well hello, I’m in this exact situation right now. It’s just me and my boss at a non profit. I am fortunate that it’s turned out very well.

    It’s an extremely tiny operation with a small budget, so I don’t feel overwhelmed with work as the sole person (plus we have really involved volunteers and board members who help a lot). The job attracted me because I liked the field of work, the opportunity to gain a lot of experience in lots of areas, and it’s a welcome change from my last job at a big dysfunctional organization.

    I did know someone who knew my current boss, and I spoke to the woman I replaced before she left as well. Everyone had good things to say. Plus I read up on the board and read financial reports as well to make sure that everything was kosher.

    The hardest thing is feeling like I always have to be there if my boss isn’t (like if my boss is out at a meeting and we’re expecting someone to visit the office, I can’t take a Starbucks break – but I manage that by making sure I know exactly what time someone is expected so it’s really not a big deal). I thought it would be weird to have zero coworkers to chat with/be friends with, and it is sometimes, but it’s also REALLY nice not having any coworkers sometimes! Think of all the people in your office who annoy the bejesus out of you – I don’t experience any of that. I’m an introvert my nature, so I’m happy to put on music or a podcast and spend most days with just my boss for company.

    Feel free to ask me any questions!

  8. L*

    I agree with Alison, and also with Paul on doing your due diligence about both the CEO and the board.

    Another thing to think about if you’re new to working for small organizations: many worker protections/benefits only apply to mid-size and large companies. The most familiar example is FMLA, which applies to companies with over 50 employees. The ADA, which would require the company to make reasonable accommodations if your husband has (or develops) a serious medical condition or other disability, only applies if there are 10 or more employees. Others will depend on the state you live in. For instance, my husband and I learned the hard way that the New Jersey mandate for employer sponsored health insurance to cover infertility does not apply to companies with less than 50 employees–we lost tens of thousands of dollars when I switched jobs. If your husband is the sole or primary income earner for your family, these can be serious considerations–at the least, you may want to increase the size of your emergency fund if he takes the job.

    1. Manders*

      Yes, this is a very important thing to be aware of. A lot of workplace protections that teachers in particular may be used to (because they work at larger organizations, and often have unions on their side too) won’t apply. Your company may also have trouble negotiating good rates for health insurance and other benefits if it’s small (or at least, that’s the excuse my former bosses gave–it’s possible that they just didn’t have the time or knowledge to find better options).

      1. Natalie*

        With 2 employees, I think its way more likely that the company simply won’t offer things like insurance. Which is something else for LW’s spouse to be extra sure they’re including when evaluating the offer – both the cost of self-funding benefits plus any tax implications as you can’t spend pre-tax dollars.

        Also, how will time off work in this mini-company? Will your spouse be able to take a real vacation occasionally, or will they need to work?

  9. Legal Beagle*

    First, I’d echo all of Alison’s fantastic advice! Second, having worked at tiny (although not quite this tiny!) non-profits before, I would be VERY concerned with effectiveness and sustainability. A lot of people want to do meaningful work, which is great, but running a non-profit is hard work. Sometimes good intentions don’t match up with ability to do the work, or the need for the specific work someone wants to do. A person starting their own non-profit is a potential red flag to me – it can be a sign that they are more focused on their desire to do feel-good work than on if they are effectively addressing a need. How is this non-profit regarded by other organizations doing similar work? That’s a huge tell.

    I’d be digging deeply into the actual services provided and the impact of this org, as well as its funding sources. If it doesn’t seem to have diverse, sustainable funding, or if it doesn’t seem to be effectively fulfilling its mission, I would walk away. The funding issue is obvious (the sole funder stops funding, now you’re out of a job), and the impact is important for job satisfaction (if you love the mission but the org isn’t actually doing what it’s supposed to do, that can ruin what looks like a dream job on paper). Good luck to your husband, LW! Non-profit work is awesome if you’re in a good organization.

    1. LouiseM*

      +1. What can people outside this organization tell you about it? That’s what I would want to know.

  10. Anastasia Beaverhausen*

    Unrelated to the LW- but I love how when the gender is not obvious you (Alison) automatically writes “her” . I have seen it in several posts, especially in regards to leadership and it is so nice. Even as a woman, I will go back to assuming a man, and it is nice to see it turned around :)

    1. Ask a Manager* Post author

      Thanks! I started doing it when my co-author and I were writing Managing to Change the World, and it got ingrained in me and now it’s automatic. I really like it as a counterbalance to how managers are often presented as male by default.

      1. Chaordic One*

        In the same vein, I appreciate it when you refer to an administrative assistant, secretary or other support position as being male.

  11. Hey-eh*

    My aunt worked at a small organization that was just her boss, the CEO and her. And the boss’s dog. It was very niche.. think.. Welsh teapot marketing in Australia. She worked there for many years very happily and learned so many skills she wouldn’t have been able to get if she worked somewhere bigger. She has no education past high school so while she started out doing kind of executive assistant type work she had to wear so many hats she was forced to learn new skills and eventually was doing most of the marketing. The reason it worked so well though was because her and the CEO had a fantastic report with each other, and there was a good level of trust and boundaries set. HOWEVER, when her boss decided to retire she was left without a job because he just closed up shop instead of selling. She had a very, very difficult time finding work after that.

    1. Bea*

      He retired but couldn’t help her with a reference? They didn’t have a client base to vouch for her talents?

      This breaks my heart. My biggest fear changing jobs after my long term placement doing everything for my boss was what happens when he dies. Then it went more sideways because he got hit with early dementia. His wife stepped up as my reference and could tell anyone anything they needed to know. However in the end only one person checked my references.

      I also used a client who I worked frequently with. I served as a reference for a sales rep for one of our customers years before that. Same idea, her boss was a sole ownership and great but she was moving on for greener pastures with good standing. I’m shocked so many years and a healthy happy retirement was so sad for her, I hope after she did find something things were good for her ever after at least.

      1. Hey-eh*

        He was a reference but from what I understand (and keep in mind I was getting it third hand) because the organization was so small and she did wear so many hats, after that it was tough for her because she was kiiiind of a marketer but didn’t have the schooling to back it up. She wasn’t quite an office manager because she did more than that, so those jobs weren’t at her pay scale. She did web design but not well enough for those jobs. Her role was really fractured so therefore her experience was really fractured.

        1. Bea*

          Ah that’s interesting and still frustratingly sad. Nobody besides large scale places give AF about my lack of schooling when they see my resume but I focused on accounting as my go to when I left and peppered in my other skills of being able to tweak websites and hustle vendor into price breaks. I can see how it’s hard to encapsulate a wide variety of duties that don’t necessarily jive in other business structures.

        2. LQ*

          I totally struggled with this when my org collapsed. I was really good at a lot of stuff but I was basically never already as good as the people who only did that one thing. I did a lot of informational interviews and started out somewhere at a fairly entry level role (and rose up internally) after because it was a bit of a challenge to say I was great at something when I was great at that size. It’s just different when you’re that small. Which is also an important thing to think about.

          1. Hey-eh*

            Oh totally. She had the added issue that she was 53 when she was job hunting, and hadn’t had to look for a job in 20 years. I’m happy that she is now in a role that she loves in the same field but she’s doing something much different than before.

  12. TootsNYC*

    I think you also want to know a lot about the financing of this organization–where does the money come from (the money that will fund your paycheck)? How stable is that flow of cash?

    How honorable is the organization?
    How well-organized?
    And how likely are they to actually succeed at their nonprofit goal?

    If it were a business, you’d want to be really thorough in investigating their financial health, the likelihood that their product or service will be in demand long-term. And how well-organized they are in delivering product/service to market/customers.

  13. Jesmlet*

    Take the dysfunction of a non-profit and add to it the size of the company and you’re looking at a high chance of a disaster. Questions that’d be on my mind:
    1. How does the CEO react to suggestions, criticism, general disagreements, etc.? What other checks and balances exist, whether it be a board or other highly involved volunteers?
    2. What overlap is there in the work between himself and the CEO?
    3. How would he be managed considering the remoteness of the work? How much autonomy is there in the role?
    4. How would he extricate himself if he chooses to leave? Will the CEO react reasonably if he tells her he wants to leave and asks for a reference?
    5. How long has the non-profit existed? How stable is the cash flow? AKA what are the chances he’s going to be not paid on time on occasion?

    This would be a hard-no for me. I’ve worked for a non-profit and I’m currently working for a small company and the idea of combining the dynamics of the two seems nightmarish.

      1. Jesmlet*

        Yes, I should qualify that I’m definitely tainted by Old Toxic Job which was in the public’s eye very well-run but from an employee’s perspective, an absolute shit show. I also don’t do well with bureaucracy and red tape which is a staple of many non-profits.

  14. Hapless Bureaucrat*

    Funding and training. Not only how stable is the organization’s financial picture but how prepared is the organization to do whatever performance or fiscal requirements its funders have for it? What are the resources for your husband to get whatever training he needs to do his work? How easy or hard are the funders and board to work with?
    I come at this from the perspective of someone who funds wee tiny organizations, obviously, and I’ve seen a lot of them struggle with internal controls and training.
    You can love your boss and your mission and yet drown under the weight of resources you’re expected to have but have no way to get, if the organization has extended itself too far too fast. On the other hand, with a good boss, good board, and good strategic plan, your husband could pick up a breadth of experience it would be hard to get elsewhere.

  15. Pam*

    Something else to worry about- with a public school system, he probably has health insurance, other benefits, possibly a pension. How will that be replaced? Will he lose vesting in the pension scheme?

    1. copier queen*

      I wondered about this too. The public school system I work in offers excellent health insurance at a relatively affordable price, plus free life insurance, lots of paid holidays, generous amounts of vacation and sick leave, etc. The pension system is good but if you leave before being vested at 10 years of service, you only get your pension contributions – not what the system contributed. So basically, if you stay 10 years and 1 day, you get twice as much money. Also, job security with the public school system is very solid, unless you are a terrible worker or an unsafe person.

    2. VioletEMT*

      This was my exact same thought. My other half just left state civil service to go work for a small nonprofit. Before they did we had a long conversation and did a ton of research into the benefits switch, and re-jiggered our saving scheme and investment strategy as a result. The benefits hangup alone was almost a dealbreaker, but we made it work (they really, really wanted the job change). But don’t minimize the impact of getting out of public service benefits, especially if you’re in one of the few states where they haven’t been gutted.

  16. Jaguar*

    Does it strike anyone else as ridiculous that the owner refers to themselves as the CEO? Like, this is to differentiate themselves from the other officers, executive officers, and non-officers of the one-person company, presumably?

    1. Bea*

      No. You have to have a former title for a business structure. You aren’t the “owner” in this case because it’s a non-profit and that sounds super awkward.

      Other owners refer to themselves as President. It’s just a thing that happens. It goes along with our other post today about job titles though.

      1. Manders*

        Seconding this. They might also call themselves the “founder” or some similar title. It’s only really a red flag if the CEO starts showing other signs that they don’t understand the level of power and influence they really have (like declaring that since they’re the CEO of a company, they should start writing business books and teaching seminars about how to succeed in business).

  17. Yeah*

    I spent 18 months working for an organization where I was the only employee other than my boss, who was the owner/principal. I found that the most difficult thing for me was since I was the only employee, every single task that the boss didn’t want to do or deemed was below an owner/CEO’s pay grade, fell to me. That might be different for the OP’s husband since there will also be volunteers, but we also had interns, and there were many things that the interns just weren’t able to do, for various reasons. I would guess it would be the same with volunteers. It was fine part of the time, but when we were really busy or when there were big tasks (like packing up and moving the office), there was no one else to shoulder the responsibility or to ask for help. It also meant that it was difficult for me to take time off or be out of the office for any reason, including basic things like taking a lunch break away from my desk every once in awhile. My advice to the OP’s husband would be to clarify ahead of time the CEO’s expectations of his workload and output/productivity, and approach to time off/personal time. I didn’t think about those small, every day things being an issue when I agreed to be the only employee.

    I’ll add that I shouldered a disproportionate amount of the financial ups and downs of the business. When business was slow, and cut backs needed to be made, I was the only employee that my boss could address that with. I was asked to take a pay cut and eventually to have the structure of my compensation changed altogether (which ultimately led to my resignation), and it may have been less of an issue if there were more employees to spread it around. I’ll admit that I’m not totally sure if that would’ve made a difference, but perhaps. Something to consider when the income of the business/organization can be volatile.

    Finally, to your point, Dawn – my boss had issues with professional boundaries, too. She ended up wanting me to do a lot of personal assistant-type work (which was not part of the job when I was hired), such as running personal errands for her, helping her clean out her family’s storage unit, or working at her house a lot instead of our office so she could “work from home” with her kids.

  18. Thomas*

    I think it would be entirely appropriate to ask for formal references from the potential boss. Just like the boss would want to hear from former managers, I think OP’s husband wants to hear from former employees.

    I also think that OP’s husband would want to investigate the competency of the board and make sure that he has a relationship with some board members before starting.

  19. Ann Furthermore*

    I work for a very small company now, after spending most of my career working for large corporations. It’s different — not necessarily bad, but different, and there are things you should be aware of, and decide if you’re OK with before making a decision.

    You are your own IT department. There’s no Help Desk to call when you’re experiencing technical issues. It’s you and Google. On my first day at my current job, my boss handed my laptop, still in its box, and told me all I had to do that day was get it set up and configured. When I asked about a couple other programs I’d need, she told me to go ahead and download them and expense them. A few months ago I kept getting the blue screen of death, and spent half a day screwing around with it. I finally tracked down this free application called (I think) WhoCrashed, which will tell you what caused your blue screen error. Then after that I found that my laptop had some out of date drivers, and after I updated them, things stabilized.

    If this is a role where you’ll have to travel or incur expenses, then you’ll be using your own personal credit card for that. That’s what I do, and I don’t mind, because I can get the miles on my card, but it’s something you need to be aware of.

    Most of us work from home 2-3 days a week, and/or odd hours, so there’s no company phone network. We all use our cell phones. It feels weird and invasive to me still, after almost 18 months, and I wish I would have known that I’d have to be giving out my personal cell number to colleagues and clients. It would not have stopped me from accepting the job, but it would have been nice information to have.

    1. Penny*

      +1 to being your own IT department. And office manager. I work for a two-person nonprofit and it’s the first time I’ve ever had to deal with printer issues myself!

      1. Bea*

        Cackling because I know so many people with this problem but I’ve always been first line of defense. You’re in good company, the printer will not explode and please resist hitting the thing!

        First job ever. 19 yrs old. My boss feared technology(long story) but he did use the fax machine. He explained it to me and added “sometimes you gotta smack it. Like this! *whack whack*” (Spoiler, it worked for me without the abuse!)

        1. paul*

          But I want to hit it…I know our last office printer is still in deep storage, I’m wondering if I can get it in severance when I move in. I really want to Old Yeller that thing.

    2. Manager-at-Large*

      advice for Ann ^^ — get a Google Voice number to use for office and refer it to your cell. There’s no reason these days to have your actual cell# out there in this context.

  20. ABK*

    OMG. Sounds like at best it will be a huge transition. Has he always worked for the public sector? The public sector provides an amazing amount of security: management, unions (possibly), pension, benefits, HR, IT, hiring processes, general buracracy etc etc etc. This probably sounds like a really exciting opportunity, be he has to be ready to leave all of that behind, and be subject to this bosses whims. When I was in this situation, it fell apart because of a too vague job description and general tension between my boss and I since there was no one to dilute it. Along with everything stated above, he should hash out a very firm and specific contract & job description and arrange for it to be updated throughout the year. 6 months is too long to wait to readjust the expectations and contracts if his job turns out to be different than they both anticipated.

  21. Competent Commenter*

    Alison’s got great advice as always. My additional take on this, as someone with a long history of working for nonprofits, is to really look hard at the benefits. Your husband may have a retirement plan at his current job, since it’s a government job, but I bet there isn’t one at the nonprofit. As someone over fifty, I really have a lot of regrets that I spent so many years working in a field with no retirement benefits (and originally no health insurance, either!). I’ve moved to working for a public university in great part so that I can get some money into a retirement plan, but it’s going to be paltry at this point.

    Also, I second how difficult it is to work in such a tiny office. I have worked in similar and they were dysfunctional and crazy. I know YMMV, but for all the reasons Alison mentions, you’re more likely to have a bad work environment if the organization is that small. And oh man, dealing with the board and volunteers…shudder. They have an outsized impact on you when they’re heavily involved.

    1. MommyMD*

      I couldn’t work where a single person had control over my destiny. It takes little in situations like these for it to fall apart.

    2. a different Vicki*

      That may be more about organization size than about its being a nonprofit: I had better benefits at the nonprofit I worked at early in my career than at the for-profit companies I worked for after that.

      It was pretty clear that the nonprofit figured they were offering a tradeoff: a lower annual salary, but significantly more paid time off, good health insurance, and excellent 401(k) matching. [Technically a 403(b) plan, but it works the same way.]

  22. MommyMD*

    Benefits. Right now he probably has a very good package. Take into consideration paid time off, sick leave, paid holidays, 401k or equivalent, disability coverage, copay and deductibles for dental and medical. These can be worth tens of thousands per year. If you work and can cover him what happens if you lose your job? My employer know keeps me insured for 18 months if I get a devastating illness and can’t work. Make sure to take all this into consideration. Especially if it a start up. You’ll have to have enough saved to live if his job ends on a dime.

  23. Hey Karma, Over here.*

    Don’t do it.
    So many reasons why.
    Here’s one that jumps out at me, though:
    Coming from a school district (read: large corporation) the culture shock will be devastating.
    How do you balance life and work when you are the office? Vacation days, sick days, holidays…it’s you. And if he’s working remotely, what guarantees are there about when he is off the clock? Scope creep is not just for projects, it’s for jobs as well. How many hats will he wear and how much time will he spend in them?

  24. Legal Seagull*

    There is some really wonderful advice on this thread. To it, I would add: after 15 years in the nonprofit world, I urge your husband to ask the same questions he’d ask of any going concern that’s recruiting him. The main difference between a for-profit business and a nonprofit is that the former exists to make money after paying its bills and the latter exists to achieve a societal good while paying its bills. However, no matter the good intentions that undergird nonprofits, they still have to pay their bills – and that includes your husband’s salary, benefits and expenses.

    Thus, your husband should ask: what’s the business plan for the organization? There should be one and, ideally, a mission statement and goals. If there isn’t a business plan, that’s a red flag that your husband shouldn’t give up his day job just yet.

    Second, how is the organization funded and for how long? Here, your husband is entitled to know if there is grant or other support, and for what period of months or, best of all, years does it extend. Also, does the support cover all of the nonprofit’s expenses or will the CEO and/or your husband be expected to go out and raise money? It’s a red flag if the CEO cannot or will not discuss funding for what will be a two-person operation. It’s similarly a red flag if the CEO expects your husband to go without a salary or front expenses that supposedly will be paid back at some undefined time in the future when, the CEO predicts, grant money and donations will roll in.

    Third, what will be your husband’s job? Fundraising, coordinating volunteers, drafting grant reports, anything and everything the CEO doesn’t want to do? Even though this will be a two-man shop, your husband needs to know up front what he’s expected to do and how that fits in with what the CEO is doing and the overall mission and goals of the organization. If your husband is not willing to serve as Watson to the CEO’s Holmes, this probably isn’t the job for him.

    Fourth, if your husband is expected to raise funds, how does he feel about that? Does he have any special skills at that? I know plenty of people in the nonprofit world who are committed to doing the work on the ground, but would run a broken mile to avoid others for money to fund the charity’s work. And, yet, few nonprofits can survive without donations and a fundraising strategy. If your husband is one of those people who hates asking others for money, he’s probably better off staying where he is now.

    I hope this helps as you consider this transition. And remember: if your husband wants to work in the nonprofit world, this is not the only way to do so. He can decide that this isn’t the right place for him, but find another place that will be right for him down the road.

  25. ellis55*

    I did this for about one year and the reality was somewhere between horror stories and bliss, I guess like any job. To add to the above, I think the biggest consideration is really how this fits his larger career goals for himself. Smaller organizations are a little less stable, and you can’t get quite as comfortable as if you’d just signed on entry-level for a large corporation that will be able to afford your salary indefinitely. If this doesn’t work out, what’s the next step? Does this get him closer or further away.

    Also – you have to be a little more diligent about networking when your team is small because you might not find the same opportunity to create connections. You also have to understand that it can be much harder to job search when your job is so all-encompassing. When you do a little of everything because it needs doing, it can be much harder to articulate where you specialize – what you really *do.* These jobs can become a lot like Executive Assistant jobs, ultimately – and that’s how outsiders often see them, even if what you’re really doing is something more like recruiting, event planning, design, etc. Is he the type to pursue professional development opportunities in whatever he most wants to be doing in 5-10 years, and to do it often? It’s so, so important to keep his skills sharp and name top of mind in that field.

    Finally, what’s his personality? You have to be a lot more assertive to succeed in these roles because you’re always advocating for yourself all on your own and to the highest decision maker. With no HR as a buffer, you need to be really comfortable stating your needs early and often and setting boundaries when you need to. If that doesn’t sound like him, his boss may even be lovely and this may not be the right environment for him to feel happy and fulfilled.

    I ultimately left my opportunity for a larger organization for all the reasons folks are articulating above, but what I did gain was the opportunity to try my hand at a lot of things I might not have otherwise been allowed to do at such a junior level. It was worth it to me to swallow some of the negatives so I could say I’d planned an event for [x] people, had worked on grant-writing and the annual fund, etc. Those are specialized roles that larger organizations probably won’t let someone who isn’t seasoned anywhere near. If that’s what he wants, and he’s cool with all of the above, I say full speed ahead.

    1. Bea*

      “signed on entry-level for a large corporation that will be able to afford your salary indefinitely.”

      We see huge layoffs and downsizing in giant corporations, this is dangerous thinking! You’re never ever in a position where you can’t be eliminated.

      However it makes me remember to add that be sure that you’re aware that this is another reason having payroll set up properly is critical. They need to be reporting you as an employee and paying into unemployment insurance.

  26. Glomarization, Esq.*

    My background: 20+ years’ experience with non-profits. My advice: I’d hesitate big-time before hiring on at such a tiny organization, particularly since LW’s husband hasn’t worked with a non-profit before. It’s a very different environment than a for-profit business or state-funded dealio like a public school. So LW’s husband will have a serious learning curve on top of the expected challenges that come with moving to a different workplace and having only one co-worker.

    Maybe the organization is flush with cash and has a seemingly never-ending source of money (huge endowment or foundation trust funds or something). And maybe the CEO is brilliant. But on a practical level, I suspect that LW’s husband is being brought on to do compliance work: paper-pushing and reporting and scut work that will be very unfamiliar. It’s not rocket science, but there are issues that trip people up, smart people who are working in good faith, in ways that can be very expensive.

  27. Just Allison*

    My brother in law works at a company where its only him and the CEO. He really enjoys it and he loves the work and the experience its giving him. That said he does have complaints, he gets frustrated seeing that his boss(owner) has a lot of down time while he is working. He says that even while there is work to do it is very easy to get bored, just from the lack of co workers. He does enjoy the flexibility that being a two person company gives, they both have families so having to run out for a family emergency or even getting a week and a half paid time of paternity leave was amazing from him ( he got two weeks but my sister sent him to work sooner)

  28. EditorInChief*

    There isn’t the level of checks and balances when you’re working in a small company. After getting laid off with excellent severance from a big corporate job I decided to work at a small company of 5 people as a change. Never again. I did extensive due diligence with the help of industry friends before signing on, but soon after the first year our CEO/Owner fired my boss and inexplicably bought an unprofitable competing company and spent all his time working at that business, at which point I started interviewing for a new job. He siphoned off money from my company which was highly profitable to prop up the failing business. The final six months were a nightmare with staff salaries cut in half, health insurance eliminated, freelancers not being paid, and finally the delayed pay checks to staff. Between the shady financials that seemed to be run like a shell game, a CEO with no checks and balances, who had no experience in our industry and didn’t understand how it worked but didn’t hesitate to micromanage us, to having no HR, no IT, no cleaning service, no office supplies, I will never work for a small company ever again. I don’t care how well run it seems, I was thrilled to go back to a big corporation.

  29. Mrs. Wednesday*

    I’ve been in small (but not this tiny) non-profits for almost 30 years and two things come to mind: the board of directors and 990s. Please look carefully into its financials. They should be available through sites like Guidestar and, if you can’t find them, that’s a red flag. Ask to see the most recent strategic plan, too.

    I, too, looked askance at the “CEO” title for such a small shop because I’d expect a Director or Executive Director. I also wondered if this organization is still in its seed-money stage. As far as growth goes, this could have great potential — if planned, sustainable growth is an organizational priority.

    I think the best-case scenario is a kick-ass leader who is happily — yes, happily matters — paired with a strong, working board. If you can’t find info about the board easily, or it doesn’t seem to actually do anything, run, run, run. So many reasons but two are “fiscal integrity” and “CEO accountability.”

  30. Geneva*

    I’ve worked at an organization as the CEO’s only employee (not by choice, but that’s another story) and I strongly encourage your husband to decline this offer. This scenario is all stress and zero security. It also makes it difficult to move on. Let’s say your husband wants to quit. How long is it going to take for him to transition his duties to someone else, and will the CEO have a negative reaction? Then there’s moving on to a new job. I’ve had potential employers question if I knew how to work on a team after working independently for so long.

    Honestly, he might as well be a freelancer.

  31. Interested Bystander*

    My mother in law works for a tiny Non Profit Organization (only 2 FT employees and like a dozen PT/Temp.) She saw this issue from the reverse side – Board hired someone that they didn’t do real due diligence on, and things went sideways very quickly.

  32. NW Mossy*

    This sounds like the non-profit equivalent of joining someone’s garage start-up, and it’s worth thinking about it that way in terms of the personal and professional risks. We all want to believe that we’d be smart enough to get in on the ground floor of The Next Globally Transformational Thing, but the reality is that these are far outnumbered by the half-baked ideas that went nowhere and left significant wreckage behind for those directly involved.

    Alison’s point about interviewing the boss is a good one, because you need to look at this as if you were hiring them to be a CEO. What evidence do you have that they’re an effective leader and likely to take the organization to a place that you’d want to go? There’s a huge difference between someone who’s used to the reins of authority and is branching out into a different venture and someone who’s never done it before but feels like they’d do better than those with experience.

    I’d also try to suss out what this person’s decision-making process is like. Every single bit of launching a new organization involves decisions, and ideally your style will work well with the CEO’s. You should be on the same page about how much autonomy you’d have to make your own decisions, the pace at which decisions are made, what factors matter in making decisions, how decisions that turned out poorly are handled, and much more. If any of those are out of sync, it’s going to make every day an uphill climb.

    And finally, I’d inquire as to whether or not the CEO has family or close associates involved in the organization in any capacity. If that’s the case, be prepared that whatever dynamics the CEO has with those people will bleed over into the organization, often in ways that are very difficult for non-combatant employees to deal with.

  33. SuspectedDragon*

    Employee of small non-profit here – we have 4 full-time people, including the president, with the good portion of the organization’s work being done by volunteers. I asked a TON of questions during my interviews (funding for the organization, structure of the board of directors, volunteer recruitment/training), and I honestly think that factored heavily into me getting the job. President was impressed that I was even thinking of these things, and I was able to feel comfortable moving into the role.

    That being said, the organization is a trade association that’s been around for 50+ years and has a strong reputation in the industry and region. Had this been a start-up, I don’t think I would have taken the job. So YMMV. Really just wanted to chime in with a happy story that small/non-profit doesn’t have to equal dysfunctional!

  34. LQ*

    I had this job. It was my best job ever. It was my worst job ever.

    When my boss was amazing it was incredible. I got to do things that were remarkable, I learned so much, so fast. I got to basically develop my own job, help drive the direction of the organization, learn 10,000 things that I would have never had the chance to do. I cared passionately and I knew every single day what a huge impact I was making.

    And then my most amazing boss ever left. And things were sort of well fine, until they weren’t, and then they were all on fire. Entirely. Completely the worst. Finding grants between used condoms kind of bad because we needed that grant document and we didn’t know what was in that stack.

    When it’s good, it’s very very good; and when it’s bad, it’s very very bad.

    If I knew it was Awesome Boss, I’d do it again in a heartbeat. But for anyone who I wasn’t already entirely sure was Awesome Boss I’d never do it again. (Partly because the experience has made me more risk adverse.)

  35. Jana*

    I agree with Alison’s advice to be cautious and really consider all possible issues here. I worked at a very small nonprofit where the president/CEO was the only person on staff there longer than 6 months. A lot of how well this kind of situation goes depends on the person you’re working with, so the experiences different people have with this type of workplace. That said, there’s one overarching matter that should definitely give you pause: if there’s a problem with the CEO, your husband may have no recourse (except to quit). That’s a difficult position to be in. Operations, practices, and behaviors at organizations like this are built around the preferences/expectations of one person, so it’s important to really know that person’s professional nature.

  36. Cowgirlinhiding*

    Are there going to be any benefits with this job? An academic job usually comes with paid time off, holidays, 401k, insurance and possibly sick leave. Would this job offer any of those things and is it a salary position, where the work will never be completed or he will have a hard time taking time off because he is carrying all of the work load. This would be big question if I was looking into a two person team. Who is managing the volunteers? Would it be split between the two people, what is the management style they can agree upon if they are both managing? Just some things to think about before jumping in with both feet.

  37. cheluzal*

    I’m a teacher and I advise not to quit the district, but take a year personal leave. That way if it doesn’t work he has a job to return to.

  38. You Know It*

    I worked with someone for years in a small office that was part of a large company that had HR, payroll, etc. I thought I knew him, but working *for* him was a nightmare. It didn’t really matter that it was just us plus an occasional other employee or business partner (who never stayed long). This was his “baby” and I was just a commodity he could use to make more money, look successful and blame for anything.

  39. OP*

    Thank you all for your (as always) excellent advice! What really jumped out (among other tips of course): when/if the time comes to move on, the founder is the only reference! What a great (logical) point.

    A little more background based on some comments:
    – The founder didn’t call himself the CEO, I did that for ease of reference. I’m not in the non-profit world, I’m sorry for any confusion that might have caused!
    – Also, there are other team members, but they’re self-funded (they fundraise their salaries). So there will be more people “on the team,” but as of now husband would be the only W2 employee.
    – Husband knows the founder pretty darn well. The nonprofit hosts regular outdoorsy retreats and he’s gone on retreat with the founder a few times for long weekends — there’s lots of personal disclosure, healing, team building, etc. (That said, the advice to ask for references who’ve worked with the founder is priceless! Of course!)
    – Husband is eager to leave the teaching field. We’re both former teachers. Saying sayonara to the public school system would be a huge benefit here.
    -Benefits are a big part of the deal. If he got an offer, it would be to be funded for 3 yrs at matched salary and benefits to his current job, with room for growth if he improved revenue (which, since they aren’t doing much for revenue, is a strong possibility!). Since I freelance, he’s the “anchor” job that gives us benefits and a regular paycheck, and he’s been very clear about that.

    Thank you, thank you, thank you!

      1. You Know It*

        Yes. This. I have spoken to people who have been offered those kinds of positions, and they’ve all walked away and been glad they did.

        The place isn’t viable if people have to fundraise their own salaries.

      2. GRA*

        I believe this is actually against the AFP code of ethics for fundraisers. This is a HUGE red flag!

  40. SallyForth*

    I would add some suggestions:
    -is the CEO also the founder? Founder CEOs of small not-for-profits (especially ones that have no other employees) are infamous for being extremely difficult to work with
    -check out the board. Do they have a good mix of people who are in the field, with an accountant and a lawyer thrown in for good governance? Do they have a good board turnover?
    -check out the financials. If it feels awkward to ask the CEO, you can look online. If you don’t understand financials statements, ask someone who does.

    1. J*

      I have worked almost 20 years in nonprofits, and I have to agree about founders. I would have fewer reservations if the CEO was not the founder. Founder’s syndrome is a real thing, and the only reason I’m still at my current job is because the founder announced her retirement after my first year. I spent almost all of that first year job hunting, because she would not allow me to do the job I was hired for. While their passion is admirable, it is common for founders to expect the same level of 24/7 availability and commitment that they have. It is also common for them not to trust their employees expertise because they feel they know the mission/cause best.

      While I have loved my career in nonprofits, I will never again work for another organization that is still run by the founder.

    2. Gazebo Slayer*

      Not just founders of small non-profits – I know from experience that many founders of small for-profit businesses are awful, power-tripping people. (Sometimes they went into business on their own precisely because they were such jerks that no one else would hire them any more. This plus the financial resources to start their own business and the reverence our society accords to small business founders makes for a deeply, deeply toxic recipe for egomania.)

  41. Anono-me*

    In your update OP, you say that you freelance and Mr OP has the anchor/safety net job. I don’t know if I would consider a second position in what is now a one person npo that secure.

    I worked part time in a one person org. and loved it. FT would not have worked at all.

    Both would mean that I personally couldn’t make the leap.

    This wacky idea is a very very very long shot. Since this is a newly created position and there is less than two months left until summer; Would it be possible for some volunteering and a trial run over summer break?

  42. Cody's Dad*

    I’d suggest reading over your husband’s school contract. Depending on the contract and the language written, he may be able to take a one year leave of absence starting in September. If things aren’t working out at the new job, it could be his “safety net”. Also,think about retirement money as a school employee this is done for you and with his new position it may or may not affect what he brings home. Good luck!

  43. nnn*

    Another question to possibly ask the CEO (could be approached from the point of view of trying to see if they’re mutually compatible) is to ask her what traits she has disliked in employees and volunteers in the past. I’ve found you can learn ab lot about whether you want to work with someone based on how they talk about employees they’ve disliked.

    1. Sunshine on a Cloudy Day*

      YES!!! I find it very telling! It’s not so much the specifics of what they say EG: “I don’t like people need constant hand holding” – I’ve found it’s like 50/50 on whether that is actually accurate. It’s more about the tone they use what types of things they focus on.

      I interviewed with one woman who just went on and on and on about how the person I’d be replacing is constantly on their phone. Which, fair enough – that is frustrating and unprofessional if they are on their phone when other work needs to be done. I tried to explore that a bit more – re: expectations, pace of the job, is there ever downtime and how is that expected to be handled, but all this person could do is go back to how the current person is always on their phone. This was a huge red flag to me. She could only speak to the employee being on the phone, not any of the specific results/work tasks that were not being done. That told me she was more focused on the method than the results, and I don’t do well with that type of person. There were other issues as well, this is just the one that just jumped out at me as the most obvious/easy to grasp on to.

  44. FormerSmallBizWorker*

    I’ve been in this situation (except it was of four instead of two) and I would be really cautious.

    There are few word of cautions I would like to share:
    1) Your benefits package may be limited or next to none — make sure you know what you are getting and don’t take it as granted.
    2) Job description and salary negotiation should take into account that you will certainly have to wear multiple hats. This is important that with an extremely small company, you may be asked to do things because “there aren’t anyone else available to do it” — be sure you are setting appropriate expectations of what you are willing to do, as well as compensation for such extra work.
    3) Make sure to agree on review cadence. There’s no HR, and there’s no real review cycle. (Although competent manager would have one.) It’s very easy for these things to slip as there’s no oversight.
    4) Be aware of possible misclassification!! (hired as independent contractor while you are doing fulltime gig.)

  45. Godzilla the Kitty*

    I once did an internship at a tiny non-profit just like this (so the stakes were much lower since it was a temporary thing) – my boss and I literally worked out of one room at opposite ends of a big desk. Luckily, my boss was amazing, and if I could’ve stayed on in a full-time position, I would’ve done it in a heartbeat. So this kind of job can work out! It just really depends on the boss and the setup.

  46. Scandinavian Vacationer*

    Also consider the virtual nature of this potential work environment. If there is not enough facetime with the boss, it could jeopardize the working relationship.

  47. LissyLou*

    Definitely be careful with a tiny company! I left an extremely rigid Fortune 500 for a tiny company with (supposedly) more autonomy and the potential to actually feel like I was making an impact. Big mistake! Boss, who was lovely in the interview, was an absolute tyrant- worse than anyone I have ever experienced professionally or personally. Two months was all I could take.

  48. Juniperfj*

    I was in a very similar experience in a tiny non-profit. I didn’t have all the information that Alison recommends getting beforehand, and I wish I had! I am writing my very first comment on AAM so that your husband can learn from my mistakes :)

    When I started, I was in a director-level position in an organization with an executive director, two project managers, and an intern. I was told in my interview that, as it was a small team, I would be helping with a little bit of everything in addition to my main responsibilities, which was fine. But I made a mistake in not probing more deeply on the amount of time that would be spent on other tasks and on the financial situation of the organization. I ended up spending most of my time on development, which is NOT a strength; I found out after moving cross-country to take the position that the organization was on thin ice financially; our organization applied for grants willy-nilly and then started projects to fill the requirements of the grant; project managers resigned and were not replaced; my boss didn’t fill out the paperwork for the internship program on time and we lost our intern for the coming year; my boss and I didn’t really jive personality-wise; there was no HR department and my boss occasionally got behind on bills and my health insurance was cancelled for non-payment; the local non-profit world was insular and I found it hard to make inroads with other larger organizations we collaborated with. I did not want to continue in the job if it were just me and my boss, so I ramped up my job search.

    This non-profit job could be an amazing opportunity for your husband IF the right boxes are ticked. After finding the answers to the questions about financial stability and CEO’s style, your husband can do some serious soul-searching about what he’s willing to deal with to take advantage of this opportunity. Does he thrive on variety in his job? Do you have a job that provides stable benefits and a salary that would allow him to take this risk? Is he very introverted or extroverted, and how will that impact his comfort with the work? Does the organization plan to grow and hire new people? What opportunities for collaboration and support are there in the local non-profit community, and is he willing to pound the pavement and reach out constantly to find them? Where does this fit on his trajectory? Etc.

  49. Ides of Pi*

    I once worked in a small three person office. It turned out to be the worst job experience. The founder and CEO, had quite the temper. She asked me once to clean out the office closet during the weekend. I had a family emergency (my father was rushed to the hospital) and was unable to do it. That Monday, she curses at me and said, “if I was lying she was going to kill me.” I quit right then and there. I lasted 9 months before I quit. i was told that up to then, I had stayed the longest.

    So what I am saying is, it depends the person you will be working with. 40 hours or more a week is a lot of time if you are not going to get along. If you think it is a risk you are willing to take, then go for it.

Comments are closed.