I asked an interviewer for his own reference — and he thought it was weird

A reader writes:

The other day I had an interview with an entrepreneur who looking for a part-time assistant and who essentially runs a one-man operation. He has several contractors, but there isn’t an office where many people meet regularly, that sort of thing.

The interview went more or less okay, though he was a bit clueless — like, it took 75 minutes because he took a lot of time explaining to me background details on projects that could have waited, and he didn’t ask me many questions about my work experience. Still, I expressed interest in moving forward because it seemed like work I was well suited for, and I need the employment!

As we were wrapping up he asked me if I had any questions, and one I asked was if he was able to put me in touch with any former employees who had held this role. He totally blanched at this and was obviously extremely disconcerted. He said he had never once been asked this in 18 years of being a business owner and it felt it was extremely odd. (It seems worth nothing that it was only five years ago that he became one-man entrepreneur, and in the past he had run a bakery, which is not a context where I would have asked for this kind of reference, seeing as I could just ask to visit the bakery while it was operating and observe directly.)

He said he would think about it, and then later said he might put me in touch with his “best bud,” who has been a contractor with him for most of his 18 years running businesses. This isn’t the kind of reference I was hoping for, but I didn’t want to push back too hard.

I’ll also note that he said that this role had once been held by someone for several years, and in the interim he had gone through a few people who didn’t work out and was trying to find someone who could join long term. This seems reasonable to me, and I had initially expected he would put me in touch with the first, longer-term employee, who I thought he had ended on good terms with. Or at least explain why he couldn’t put me in touch with her! I was thrown off by how thrown off he was by the question.

Was I totally out of line for asking this? In similar close quarters, non-office settings, I have had employers offer this kind of reference up-front, and I talked to a friend who manages a business and they thought it was a normal question and a red flag that this guy was so upset. I don’t know what to make of it and wanted your opinion.

Yes, it’s a red flag.

It’s fine if he’d never been asked this before and was momentarily thrown off and not sure how to respond. But once he thought about it for a minute, he should have realized that it’s a legitimate and smart thing for you to ask … and that offering up his “best bud” isn’t what you had in mind.

And it’s smart of you to want to talk to people who can tell you about what you might be getting into. That’s a crucial part of doing your due diligence on a prospective new job. Any decent employer should be willing to let you talk to other people who can give you their own perspectives on the job and the work culture.

In many cases, you can do this kind of reference-checking on your own, by using LinkedIn to see who in your network might be connected to someone who has worked for the company or manager in the past and then getting in touch with them yourself. You can go a few connections out to do this — even third- or fourth-level connections can work. You just ask your closer connections to make the introduction. (I actually just coached someone through doing this, and she ended up turning down a job offer based on what she heard about the work environment.) But that can be a lot harder to do with tiny businesses like this, so just asking directly in this context is smart and savvy.

But honestly, even regardless of references, I would be very wary of ever taking this kind of job unless you see a lot of evidence that the operation is sanely and professionally run. Tiny organizations — especially one-person-plus-an-assistant operations — tend to have a lot of weirdness to them and no checks and balances, teach you weird norms, and often aren’t great resume builders (although there are some exceptions to that).

Plus, with large organizations, if you see one thing in the interview process that seems kind of off, it might really just be that one thing. With one-person organizations, if you see one thing that seems kind of off, it’s almost always just the tip of the Iceberg Of Dysfunction.

All of this put together — the tiny size, the extreme reaction to your question, the eventual suggestion that you talk to his good friend rather than a more objective source, and the fact that he’s gone through multiple people in the role who didn’t work out — add up to a no for me.

{ 101 comments… read them below }

  1. GreenDoor*

    I agree this is fishy. In 18 years of running a business, and five as a solo-owner, there’s not a single person that he’s still on good terms with he can put you in touch with other than his “best bud.” No, your request was not unreasonable and yes, this is a red flag!

    1. Summertime*

      It’s even more of a red flag because the reference doesn’t need to be a former employee. Instead of his best bud, he could have put OP in touch with another contractor that he worked with often. Something to the tune of “I’ve lost touch with most of the people that have been in this role previously, but you could speak to Mr. Martian who I’ve worked closely with on a few projects.”

      And even if there were a few people who didn’t work out in his role, he could still put OP in touch with a former employee who could speak to how it was to work with him even if former employee’s skills weren’t a good match with the role. I’d hope that he was able to build some good faith with employees even when things didn’t work out.

      1. AndersonDarling*

        Yeah, if this guy thinks his “best bud” is the same as a reference, it goes to show how messed up his business thinking is. If someone asks me for a professional reference, I don’t give them my mom’s phone number. To most people it would be obvious that isn’t what is being requested, but for some people who live on the edge of reality, it is the same.

        1. Doc in a Box*

          I keep hearing “best bud” in the voice of Jason from The Good Place, which is enough of a sign to get the fork out of there!

      2. Frank Doyle*

        Or he could have still used his “best bud,” but instead of using their personal relationship as a descriptor, he could have only said that this was the contractor he’d worked with the longest.

  2. FormerExpat*

    Hi OP, I am a solo-preneur and one thing I do intentionally is to make sure that I have a few people I’m in regular contact with to serve as references. I have both people who can verify that I do indeed possess the skills that I am selling and also I have people who can verify that I am a decent human being who can work with other humans. One of the drawbacks of working by yourself is that you don’t have the social proof of a team of people with you. I realized that early on, and that’s why I have a list of people who can be my references, but who are not my friends.

    I hope this perspective serves as another tile in the mosaic of a red flag.

      1. Pineapple Incident*

        Seconded – you are adding value to your business by giving references readily who aren’t personal contacts. It’s great to avoid causing people the ‘is this worth my time/am I making a stupid mistake taking this chance?’ worry that often comes with debating hiring a solo practice of some kind.

        It’s the same in this way as asking any employer to hire you as their actual employee since you’re not a known quantity to them, and having references from prior jobs to speak to your skills. There’s no reason why people who are solo operators shouldn’t have these at the ready. People who are hiring managers shouldn’t automatically think they’ve earned that kind of trust from someone they’re interviewing, especially without the ‘social proof of a team’ you refer to, since that can help people infer that the hiring manager isn’t a total nutcase!

  3. BRR*

    This answer surprised me. While I think getting references from an employer makes a ton of sense, I didn’t know it was an acceptable thing to ask. Is this just because it’s a one-person business versus getting to be able to speak to multiple employees?

    1. sacados*

      That has a lot to do with it. Like Alison said, in an interview at a larger/typical company it’s usually considered fairly normal to ask if you can be given the opportunity to talk with some of the people you would be working with if you joined — and it’s often something that you would have the chance to do without even asking, just as part of the normal interview process.
      Whereas in a one-man circus, that’s not possible by definition so the only option is to specifically ask to be put in touch with someone.
      I think maybe that’s why it seems so odd at first glance — it’s something you often get a chance to do as a matter of course, so you’re not used to thinking about specifically asking.

      1. TootsNYC*

        also, in a bigger organization, it’s easier to go on your own to find people (via LinkedIn, or through any contacts you might have) who have worked either at the company or with the person. Or you can ask HR for such a connection.

        But with a one-person situation, there just aren’t people like that, and also that one person IS the organization.

    2. Midwest writer*

      I don’t know if it’s just newspapers, but I’ve never had any pushback from an employer when I’ve asked to speak with a current employee for a reference type thing. I mean, sure, take it with a grain of salt if you’re being put into contact with current employees, because they’re unlikely to tell you anything super negative, but I’ve always gotten pretty straightforward answers that turned out to be true once I started working there. (As a reporter, I’ve also contacted former employees at a couple of the places I had weird feelings about and their responses, while not negative, totally affirmed the weird vibes I was getting.)

    3. Antilles*

      I was also surprised because it wouldn’t have crossed my mind to ask and on the other side of the desk, I’ve never once been asked by a candidate to put us in touch with other former employees.
      But yeah, I think it’s different here because it’s such an incredibly small business. You can’t backcheck them with the other employees you speak with. You very well might not be able to check them on Glassdoor or asking around in the industry.
      I can maybe understand him not having someone ready off-hand, but not being able to come up with someone is certainly odd. I mean, even if he legitimately isn’t in contact with any ex-employees, there’s no clients or vendors or contractors who could go “well, I was never technically his employee, but he’s always been fair to me as a vendor”?

      1. TootsNYC*

        I’ve also never been asked, but I’m also part of a pretty big network, and a lot of the people who apply to me actually are acquainted with people I’ve worked with, or who know people I’ve worked with.

        So I don’t usually need to volunteer that–but I do absolutely make a point of explaining what it’s like to work with me (or, what I *think* it’s like to work with me), and I would not be put off at all if someone said, “Could you put me in touch with someone who reported to you before?”
        It would be a little weird, and of course I’m not going to give you Judy, who thinks I was rude and territorial; I’m going to give you Steve, who sings my praises. Or maybe, since I’m big on honesty and accuracy, and I want you to be happy working for me, I’ll give you Stacy, who I think had a good opinion of me but also saw my flaws.

    4. CatLady*

      Same! I have never heard of this before and I would never have thought to ask. It makes a lot of sense though, especially for very small businesses.

    5. Arctic*

      I was taken aback by the title as that seemed aggressive to me. But, in context, what she is asking for makes complete sense.

      1. Stormfeather*

        Yeah, the title struck me as someone being precious TBH – even though asking to talk to current/former employees totally make sense, and it IS in order to treat them as references as a sort… just putting it like that seems really off to me for some reason!

        1. Lance*

          I can kind of see that… but at the same time, how else would you put it? Especially in the context of a functionally one-man business, I can’t really think of any other terms or ways of putting it that might fit the bill.

          1. Arctic*

            No question it is a reference. But asking to specifically speak with former or other employees who have had the same role seems different to me than asking for references, in general.
            Like I thought she might be asking to speak with clients or former managers.

            1. TootsNYC*

              I think I might say, “Is there anyone besides you, perhaps a former employee or someone you’ve worked with via an outside company, who can speak with me about what it w0uld be like to work here day to day? Since we’ll be working together so closely, I’d like to have a good picture of what it could be like.”

          2. Stormfeather*

            I think just “former/current employees I can talk to” or whatever. Which yeah, reference works better as shorthand for the title, but it threw me off.

      2. Anonomoose*

        God, I’d love it if we could start asking for references from everyone who asks us for them. Would have saved me dragging my last landlord through arbitration to get my deposit back.

    6. Librarian of SHIELD*

      I don’t think it’s a question I’d ask often, because in most organizations you can ask your interviewer other questions that will give you the information you need about what it’s like to work there day to day. Things like “How do the employees here tend to structure their work week?” and things like that. But when the entire company is one guy and the interview so far hasn’t really given you that kind of information, I think asking to speak to a former employee is totally reasonable.

      Also, OP, the interview itself is a red flag before you even get to his reaction to your reasonable question. He rambled on at you for over an hour about unrelated projects and didn’t really ask you all that much about yourself? That’s not a good sign. This job feels like a no in neon capital letters.

    7. kittymommy*

      Same. I never would think of asking a question like this and just reading the letter I was a little surprised. Huh.

    8. Ophelia*

      Agreed with the answers below, and also wanted to add that I work for a large company, and while I’ve never had a candidate ask this, we work with a lot of smaller subcontractors, and I’ve definitely put some of them in touch with other firms that have worked with us in the past who are generally willing to be a reference for us (in this case, it’s more of a “yes, we pay invoices promptly, no we are not monsters” kind of thing), and while it doesn’t happen all the time, it does happen.

    9. CynicallySweet*

      I think the type of position here really matters. When I was applying for assistant jobs I’d ask this all the time. But at my current job (think database management) it didn’t even cross my mind to ask

    10. Yorick*

      When I took a postdoc position at a university, the director gave me the contact info of the previous postdocs, so I could find out what working there was like. If she hadn’t offered that, I could have just looked them up myself and reached out. But in LW’s situation, you’d have to ask who they are.

  4. Ben Marcus Consulting*

    I keep an up-to-date list of references available at all times. I have it categorized by former employers, former employees, former financiers, and former business partners. I make sure I have their permission to share, and I always give them a heads up if I’ve used them as a reference.

    A solo-owner with a solid background and even half an ounce of acumen wouldn’t balk at a request like this.

    The one-time I refused to supply was for a small PNW practice that was looking to replace its Administrator. I was aiming to supply Admin-On-Demand, and the exiting Admin wanted a sizable number of “references” in the form of former clients. It was clear she wanted to jump start her own endeavors by using my client list. However, I also gracefully backed out of their offer after the partner-not-partner physician wanted to know how I could protect him from patients that are constantly accusing him of sexual harassment.

    1. Tangerina Warbleworth*

      Ear doctor, eh? (EH?)

      Also, that’s a question anyone (but him) could answer:

      “How do I stop getting accused of sexual harassment?”

      “Stop being a skeeze.”

  5. SomebodyElse*

    I think I’d also be a little surprised by this question, and would have probably reacted the same… but upon reflection I’d be totally willing to give some references.

    In fact whenever I have a posting and someone internal approaches me about the position, one of the first things I tell them is to talk to the people on my team (or who have been on my team) to get their opinion on what it’s like to work for me.

    I figure that I’m pretty confident that I’m a good manager, but understand not everyone likes my style and that I have my faults just like anyone would. I’d rather have somebody having a good idea of what they are getting when they come to work for me.

    1. Cobol*

      Right, when I read the headline I immediately thought this is very weird, but under the specific circumstances OP outlined, it seems exceedingly reasonable.
      The reaction is excusable, but not having references isn’t.

    2. Rexish*

      I would have been taken aback a bit aswell. I mean it makes sense but I have never heared of such thing so I get it. I would also then understand the reasoning and ask if it is ok from a previous employee. I wonder if there are a lot of applicants for a job, ifthis would put you in the no pile just because they couldn’t be bothered with the extra work. OP, uodated so in this case it was a red flag but it’s an interesting concept.

    1. ampersand*

      I think even if OP is desperate for money, they should give this one a pass. If it turns out to be a nightmare job, they’ll be looking for a new job soon enough and trying to find a way to interview while already working, which could be especially tricky if they’re the only other person working for the boss and there’s no one to cover them while they’re out. There are enough red flags here to not even consider this job as a possibility.

    2. The Man, Becky Lynch*

      I’m glad that the OP confirms this guy pays his bills.

      But it’s a huge risk to trust someone to actually pay you when they are being so cagey like this guy! So you could actually end up working for free or worse, since people have been known to lie about “job opportunities” to harm others. Sigh, thanks for the perma-paranoia of everyone, 20/20!

      1. Tinuviel*

        Plus even if he does pay, the letter says he had one person for a long time then a string of short-term people. OP might get the job and be shortly fired/have to quit.

        Honestly if you’re so desperate for money that you’ll take literally anything, then you don’t need an advice column to tell you it’s not an ideal job. I think we can safely rule those situations out–people in them aren’t looking for advice, they’re doing what they gotta do.

  6. Campfire Raccoon*

    As someone who (professionally) helps tiny good-ol-boy businesses turn into legitimate small business- this is a HUGE red flag. Even if his last employee went out in a blaze of righteous (or villainous) glory, he should have been able to orate this to you – and at least provide some sort of backstory.

    Also, if his name begins with a D, I walked away from that crapshow without ever billing for the 50+ hours I worked on his circus, because I realized there were no monkeys to be had. Run, LW. Run.

  7. BeechcraftDriver*

    I second the recommendation against working for tiny organizations. I’ve only worked for one two-man partnership, but it was an utter dumpster fire; far worse than any other company I ever worked for. The owners of the company were inept, had shockingly unrealistic expectations (despite having 50+ years of experience between them), came up with borderline-illegal sketchy ways of paying, and were just generally terrible. I would never again consider working for a tiny startup again. Small is fine; the *best* organization I was ever a part of only had 50 people, but they had somebody who knew sales, and somebody who knew marketing, and a HR person…the one thing working for the Nitwit Twins taught me was that these often-unheralded roles are truly critical to the success of any business.

    1. Guacamole Bob*

      You don’t even have to get as large as 50. I worked for a nonprofit with 5 employees that was fine – it had a solid board of directors and governance structure, and when you added in the part time bookkeeper, the payroll service, the outsourced IT support, and a couple of contractors running certain parts of the programming there were plenty of people making it function like a normal business. Ditto when I worked for a 3-person nonprofit that had a 30-person nonprofit as its fiscal sponsor. The larger nonprofit had an office manager who managed facilities and benefits and such instead of robust standalone departments, but it all felt pretty functional and stable.

      My mother worked for a one-physician medical practice, and that seems borderline. There were several other employees and things were basically functional, but the solo boss who doesn’t answer to anyone in a tiny practice was sometimes frustrating, because things had to be done the way he wanted even if it didn’t make any business sense.

      But yeah, I’d be pretty cautious about working for a one-person-plus-assistant operation.

      1. Richard Hershberger*

        Solo boss: The thing is, it all depends on the boss whether this is a great job or hellish. Of course that is true generally, but it is especially true in a tiny organization. If my boss does something that doesn’t make sense, I can tell him this. We have been together for ten years and understand one another, and he will give my advice respectful consideration. My previous boss? Not a chance.

      2. pleaset*

        I think a lot of it has to do with what are the one or two people’s previous work experience. If someone has always been solo, then it’s more risky. I was a consultant helping an organization that started with two employees and it wasn’t bad, because both had experience in larger institutions and knew what was needed to be professional and effective.

    2. LunaLena*

      This. This right here was my experience the one time I ignored the red flags and took the job out of desperation, and it was a month of absolute dysfunctional miserable dumpster fire for me. I ended up walking away without getting paid what was owed me because I just didn’t want to deal with them in any way whatsoever, even though I had enough documentation that I would have had a pretty good case for small claims court.

      I see from OP’s update below that it’s sort of working out after all, so that’s good at least. But I really, really wish I had known this: “Tiny organizations — especially one-person-plus-an-assistant operations — tend to have a lot of weirdness to them and no checks and balances, teach you weird norms, and often aren’t great resume builders” before I took that job. The only thing I learned from it was to listen to my instincts and only take jobs where the proceedings are at least somewhat professional and normal.

    3. Daisy*

      I’ve worked for/with several one-man shops, and it went fine. I think the difference perhaps was that I found them through mutual contacts, or had worked with them in other contexts before. I found this question really interesting, because I’m not sure in OP’s position how I’d verify a business that I knew nothing about like this.

  8. AFRS*

    This sounds like my former boss (in fact, eerily similar – I’m in Pennsylvania if that helps). I would say run (based on my personal experience), but totally get it if you need the money. This is an incredibly smart question to ask, OP! Best of luck no matter what happens.

  9. Toast*

    In my experience when the employer complains about employees and not finding a good fit… that in itself is a red flag. I was in a position where I was warned by other employees right off the bat that everyone in the position only lasts about 6 months… and that’s about how long I lasted before I was let go for reasons that literally made no sense. I just looked on LinkedIn, and it doesn’t give months, and the person who replaced ME didn’t even last a year.

    1. Ama*

      Yeah, in my experience people who had an employee who worked for them for a several years followed by a string of people in short stints in the same role usually lucked into a great employee that they didn’t fully appreciate, and are unable to articulate the role and what it takes to succeed in it well enough to hire an adequate replacement.

      1. Pineapple Incident*

        Totally true – probably along with your ‘unable to articulate the role well’ thing, the role may actually have been job enough for 2-3 people, and their former stellar employee did this until they realized how underpaid they were for all of that work.. As the story goes, the org couldn’t find someone else do keep doing it for long on the same crappy pay..

      2. AcademiaNut*

        The other thing that happens, particularly in small but growing businesses is that they hired someone at the beginning who grew with the role as it became more complex. They left, and the boss expects to hire someone who can do everything right off the bat, with no training, no documentation and little guidance, exactly the way the old person did. If the boss doesn’t clue in to what’s happening and instead gets frustrated and blames the new employee, they can get caught in a cycle of hiring/firing or quitting.

    2. T3k*

      Yep. One of my first jobs out of college I took a job at a small (like only 5 people) family business (yep, red flag there already) as I panicked after having been laid off recently. I was lucky enough to know the last person who stayed there for more than 3 months to have some idea of what I was getting into, but oh boy. In the 3 months since that person left, the business had probably gone through 5 other people, then I stayed far longer than I should have (about a year) and left. Last time I checked a year after I’d left, they’d already re-posted the job again at least two times (and I can tell you they weren’t growing enough to hire another, unless they changed ownership).

    3. Arts Akimbo*

      OMG, that sounds like my spouse’s former job! They burn through employees like flash paper. It’s really disturbing. I think they just don’t know how to hire! He replaced a person who lasted about six or seven months, he lasted about seven months, and the guy who came after him lasted about eight months. And those are just the ones we know about! All fired for not performing duties that were never part of their job description to begin with. The company contests the unemployment claims every time with these spurious “causes,” but apparently the unemployment folks have a file on this company and make ’em pay up.

      Spouse has been happy and successful at his current job for ten years. This in itself says something about that previous place.

    4. TardyTardis*

      I had a supervisor once who ran through six accountants till she found one able to read her mind (but then, she finally retired before that accountant had been there a year, so she might have decided the last one sucked, too, for whatever reason). She also used to supervise more people till it became apparent even to those above her that she was bad at it.

  10. Richard Hershberger*

    For a different experience with tiny organizations, I am a paralegal. I have been working for the same guy for ten years. He was until recently a solo practitioner, though he recently took on an associate to take on some of the work load. There also is a secretary. So for most of my time here, it has been a three-person office, and is now up to four.

    This has worked because (1) my boss is a total mensch; (2) he has the skill set to keep a small business running; and (3) he is a good lawyer. So it works just fine. It doesn’t always, of course. Before this gig, I worked for three years in an office only slightly larger. My boss there had qualities (2) and (3), but he was a flaming jerk. Another common scenario is the lawyer lacking the business skills, though some work around this by having an office manager, who may also be the legal assistant, run things.

    I think the legal business may be different. A solo practitioner lawyer is not quite an entrepreneur in the normal sense. He may have no desire to expand the business. He just, for whatever reason, prefers to practice on his own. So there is nothing weird about a solo practice being well established, and around for decades.

    On a related note, I have also worked in biglaw. Never again. Give me a solo practice, with the right practitioner, any day!

  11. The Man, Becky Lynch*

    I’m clinching because a one man operation is even too small for my small business tilted mind. You say you’re still interested because you need a job and the money but this is a setup ripe for payroll issues.

    I would think he’d still be in some contact with that person who held the position for the longest time. I would also think he could give you contact information for contractors who can vouch for him. Just hooking you up with a buddy…GTFO.

    This guy reminds me of the dillweeds who are offended and shocked that in order to get credit terms they need to fill an application and pass the screening process. They love to respond with “I always pay my bills on time!”. Cool story, bro. I’ll do my own risk analysis with those references you’ll cough up or you can move on.

    I wouldn’t bother with him given the red flag on this one.

  12. Original Poster*

    Original poster here –

    I have so many updates for y’all! So – Alison, and all the commenters – you basically corroborated my own gut instinct, and that of the several friends I asked, and some of you have added some finer points to it that helped clarify my own initial reactions, so I really thank you all for that.

    I *did* end up going forward meeting with him, but on a very part-time (5-10 hours a week) basis, because I could use some money and it is not enough hours to strongly interfere with my larger job search. I went in with eyes open though, and really strong boundaries around my time, and record keeping my hours, etc since I very much didn’t trust the guy. I am currently trying to build out a fledgling free-lance career and working multiple small gigs (think, 2-3 10 hour a week jobs, etc) to get me going, and even in my best-case scenario my plan was to eventually price him out when I got some better paying gigs (I don’t see it as likely he’ll raise the hourly) and to not plan to use it as a resume or reference since I’ll have other employers from the same time period.

    Then!!! I happened to mention this gig to a new friend, who I’ve been keeping up to date as I embark on my various job hunts. And that is where I finally did, in fact, get my sought after reference. My friend, who is an extraordinarily hard worker, was let go by this jerk after 2 weeks, with an incredibly rude email. The details are sort of hilariously specific and bizarre (he thought she was late when she wasn’t, he was upset at her for eating when he invited her to work at a cafe and asked if she wanted to get anything, etc). We were at a party the other night and it started coming out that actually this guy is known to many people in our circle, and we all think he is basically a shmuck. It also seems possible that he has a pattern of only hiring Jewish woman (he is Jewish, as are all the friends in this circle – maybe it’s confirmation bias? but…..)

    My friend who worked for him assured me she did get at least paid for hours worked, and actually encouraged me to keep at it as long as it is useful for me financially. I already wasn’t expecting for it to last long, but this confirmed it for me. I have been working out a (probably just fantasy) of peacing out once I line up my next gig and can afford to leave, and basically letting him know that everyone in the community knows he sucks.

    BTW – Even without every single other red flag that I and all of you have outlined, I didn’t even mention some of the worst parts! I was discussing him with a friend after my first few shifts, and mentioned that he seemed like the business equivalent of a guy that is trying to dishonestly shmooze you into bed. He copiously complimented my cover letter despite it being Not Great (despite Alison’s loving advice, I’ll admit I was phoning it in that day. I had several *glaring* typos, and it was for a communications position….that should have been a red flag about me to him!!!), called me “mature” at one point (gag) (also, I’m 30…..) and at one point literally said “I don’t usually let people do this, but you’re so good, so….” with regard to my …..drafting an email for him. Which is pretty basic stuff since he hired me for ….communications.

    The only silver lining here, aside from a good laugh, and making some $$, is that I am gaining some insight into what kind of tasks I find satisfying and what direction to take my freelancing goals. I am doing pretty well with what I am working on, so it’s a shame it can’t be a long term gig. Luckily these skills overlap with the skills I use in a large scale volunteer organization I help run (yearly multi-day events for hundreds of people) that I use in my resume already, so I can still market them in future contexts without resume gaps or lack of reference, so it doesn’t feel like a total loss.

    Thanks for all of your validating commentary! I’ll try to hop into other threads and leave more replies where relevant and as time admits (on my way to one of my other gigs right now, in fact!)

    1. Lance*

      Regarding all your points… yeah, this guy sounds like some piece of work. But personally, I wouldn’t bother telling him he sucks in any way; people like this tend to just not hear it, and you’ve already had it validated by several people, so even if you’re not going to use him as a reference, I don’t see a point to it; other people already know he sucks, after all.

      At any rate, good luck with the continued job hunting; hopefully you can at least gain some skills from the stint there!

    2. MissDisplaced*

      If you need the money, keep this as a freelance gig. Sometimes people can be ok when you’re not the “employee.” Just make sure you get paid.

    3. Curmudgeon in California*

      “…the skills I use in a large scale volunteer organization I help run (yearly multi-day events for hundreds of people)…”

      Sounds like science fiction conventions, which is one of my side skills. Seriously, managing volunteers is much harder than managing paid staff, IMO.

    4. SciFiSeamstress*

      So he is skipping the yenta/shadchan and trying to find a wife + staff in one position….? Not surprised he hasn’t gotten a long-term candidate for that job.

  13. Clementine*

    Thanks OP for the intriguing update.

    As a general rule, I probably wouldn’t ask for a “reference” in such a case. I would say, “Do you have any former employees or contractors I could speak with about working for you?” However, it’s clear that this semantic difference would not have affected the outcome.

    1. starzzy*

      I think that’s where I would have had confusion, too. I tend to think of “references” as being people above me in chain of command who can vouch for my work from the POV of a boss. Therefore, it through me when the OP asked the boss, the only worker there, for a “reference.” Had it been phrased as you said, I wouldn’t have had a question at all.

    2. Frank Doyle*

      The letter doesn’t indicate that she specifically used the term “reference.” It’s just in the title.

      As we were wrapping up he asked me if I had any questions, and one I asked was if he was able to put me in touch with any former employees who had held this role.

      “I asked an interviewer if I could speak with any former employees who had held this role and he thought it was weird” is a little too wordy for the title of a blog post.

  14. Hilbert*

    an analogous situation that occurs to me is tenants that ask their landlords for references. The first time I signed a lease with a private landlord that didn’t use a property management company, I asked them for references just like I provided them with references for me as a tenant, but I am not sure if that is typical.

  15. Small business Sally*

    I am going to preface my comment that I understand that not all small organizations are not run badly. Below is only my experience.

    I have worked at several small organizations. Ranging from small retail shops in HS and College, to small organizations and even a small non-profit. They were all disasters. My last job was a small non-profit that was managed so badly they couldn’t pay us for a portion of time. Now that I am in my mid-30’s I am never going to work for a small organization again. There is no one for the boss to answer to (a majority of the time), no (or a very lacking) HR department. Often there is no support for issues that may arise. Know that if you take this job, there is likely to be no one to turn to if you have an issue ranging from how to do the actual job to support if something happens with management.

    Again I realize, I may have had bad luck. I realize that there are amazing small one or two man shows out there that are fabulous. I will support small businesses by shopping at them in my community but I will not work for one again.

    1. Junior Assistant Peon*

      It’s kind of like choosing between Applebee’s/TGI Friday’s/Ruby Tuesday’s versus a local mom&pop joint in a strange town. You’re not going to get a memorably awful meal at the big chain place, but you’re not going to get a memorably wonderful one either.

    2. CommanderBanana*

      Same. In small organizations the chance of one toxic person ruining the whole damn thing is too high.

    3. MissDisplaced*

      Sometimes though small places can be ok on a temporary basis for a few months. When you’re freelance its not so much your circus or monkeys.

  16. Nom the Plumage*

    I’ve worked with people to file their S Corps, LLCs, DBAs, etc. And I’ve worked to dissolve those businesses.

    ANYONE can start a business. In some states, all it takes is as little as $25 for a DBA and a clever name. Lots of people start businesses and find out they have no idea how to run one (which is why I’m no longer impressed by those who brag about owning their own company –it definitely doesn’t mean they have money or skill).

    I think talking to a contractor can give you a good idea about the business, but you should talk to more than one, especially if the one he referred is a friend. It would be better to talk to someone who actually held the role, but if that’s not possible, talk to contractors and clients if you can.

    1. The Man, Becky Lynch*

      Yes to all of this!

      I’ve had some real dimwits open businesses over the years and watched them slow burn themselves to the ground. Only to have to go find themselves employment elsewhere after awhile and carrying a “I failed” chip on their shoulders for longer than they even had a “business”.

    2. Countess Boochie Flagrante*

      So much this. My days in merchant services gave me both a lot of respect for (good) small business owners, and a pretty jaundiced view of people who brag endlessly about it.

    3. Beth*

      “I’m no longer impressed by those who brag about owning their own company”

      YES. It has about as much weight as “I’ve published a novel” — anyone can pay to publish their own unreadable e-book. It does not mean the person can actually write.

      (I just had a name go by my desk of “Not a writer, an AUTHOR!” — who had self-published one book 10 years ago. Nope, not quite.)

  17. Ra94*

    This interview sounds identical to one I had for a one-woman business…spoiler alert, the boss who ranted for an hour about my future assignments during the interview ended up being the tip of the iceberg. The previous person in my position had left after not being paid on time, and the whole thing was a basket of dysfunction. Leaving soon for a large company and never working for one person again!

  18. learnedthehardway*

    How I wish I’d had Allison’s advice at the outset of my career! I got my first “real” job out of school with a one-man business. It sounded pretty good to me, right up until I started working for him. I learned – after I was let go 2.5 years later – that I was the only employee who had stuck it out more than 6 months. The man was psychologically abusive, and I was in a bad space and unable to recognize it for a long time. Of course, when I finally did, and began to not react as he expected – that’s when he let me go. I got my references from one of the suppliers to the business, who filled me in on what the business owner was all about.

    1. The Man, Becky Lynch*

      In reality though, a lot of the people who are willing to hire non-experienced, new to the workforce folks are this kind of cruddy individual. Even the bigger scale operations will abuse the heck out of you because they know you simply don’t know any better =(

      You were still savvy enough to get a reference from a supplier, lots of people in that position are at a loss for where they’ll turn next and therefore stay captive to these awful “business” owners.

      1. That Girl from Quinn's House*

        +1 to this!

        I noticed this when I worked in aquatics. The directors who had a staff of lifeguards/swim instructors who were mostly in high school or early college? Huge red flag.

        Because there are plenty of adults who need a second job to pay off their student loans, or bolster their retirement savings, or pay their family’s bills, or want the free gym membership, or a part-time job that won’t change their hours every week, or don’t care about the money but just like coaching swim team. If you have a roster of 20 employees and you don’t have a single person old enough to drink on staff? That is a HUGE red flag.

        1. Junior Assistant Peon*

          This is exactly why grad school is such a toxic environment. People with work experience would never put up with that stuff, but kids right out of undergrad have no calibration of what a normal professional workplace is like.

    2. The_artist_formerly_known_as_Anon-2*

      I was in an IS/IT position like that some years ago, and I lasted 14 months, and, as it turned out , I had the longest tenure of any employee who came in from the outside to that group.

      Two things it taught me –

      – ask the right questions. Training ops? Advancement ops?
      – can I meet the rest of the staff that I’ll be working with?

      My late great father advised me – way back then.

      “You’ve seen bullfights. You were just in one, and escaped. Ever wonder why they never put a winning bull in the ring for a second fight?”

      He knows too much. He’s too smart now. I learned a lot from that sour experience and never walked into a bad job again, over the next 30+ years. And, NETWORKING, NETWORKING, and more NETWORKING will help.

      If you’re in what can be called a “small world” – you probably should have references from there before you get in too deep.

  19. MissDisplaced*

    Oh I worked at this type of place with that type of guy. I also didn’t get paid for a month and got into yelling matches with the owner on occasion.

    If you take the job, maybe consider a trial contract of say 69-90 days to see if you mesh. I mean, I suppose it can work out, but I’d be wary.

  20. chickaletta*

    All this. Working with your friends when you’re a small business is terribly common. It’s not a bad thing in itself, but even smart, successful, sane small business owners can have rose-colored lenses on when it comes to their business-owning pals. I’ve been burned before by a network connection who was intelligent, level-headed, and successful, but he recommended me to his best friend who turned out to be the ringmaster of his three-ring circus that he called a business. Friend references aren’t worth much, unfortunately.

  21. Sssssssssssssssssssssssssssssssss*

    This part is a red flag too:
    “The interview went more or less okay, though he was a bit clueless — like, it took 75 minutes because he took a lot of time explaining to me background details on projects that could have waited, and he didn’t ask me many questions about my work experience.”

    The employer doesn’t know how to to interview.

    I had an interview like that at an employer that was a 10-minute walk (walk!!) from my front door, in a field I thought I would like. The salary was right, location was right. The interview? An hour later, I knew about the married couple who managed it (and sometimes fought), the Office Dog, an introduction to their computer system (but I’m not hired yet…) and a long winded explanation about how I wouldn’t be expected to work late but how she was also working from home in front of the TV often. And she forgot to ask me about, well, me! And the job was nothing what I had expected. I was so disappointed.

    1. boop the first*

      the 10 minute walk sounds great in theory and it kind of is because:
      – it’s cheap
      – you don’t waste so much of your free time
      – sometimes you get dirty and smelly and this way you just run home instead of squeezing onto a packed bus

      But the lousy thing about the ten minute walk is when you decide to leave your home for any other reason on your day off. You walk near your workplace, tension and stress rises, your body thinks you’re going to work! Then you find yourself kind of sneaking around your own neighbourhood because if your coworkers or bosses “catch” you, they might think you’re free to come in and do work!

      Or maybe that’s just me

  22. Original Poster*

    Sad to say I am not in Pennsylvania, Cleveland, and his name doesn’t begin with the letter D! It’s a bummer that there are so many similar dudes out there… :/

    1. Original Poster*

      That makes it look like I think Pennsylvania , Cleveland is a place lol, but of course I mean Pennsylvania *or* Cleveland

  23. Beth*

    WOW. It is REALLY nice to hear that about “tiny organizations”, because now I understand that my first job in my current career was one of those, and that the weirdness was that kind of weirdness.

    It was a 3-person shop when I started, and quickly became a 2-person shop when the other #2 left. Then we merged with another 2-person shop. This was when the weirdness started getting bad: we weren’t a 4-person firm, we were a 2-person shop squared, and never became anything else.

    Before the merge, I’d been doing fine with my boss — he had major problems as a manager, but I required very little management. The two bosses went down a spiral of reinforcing each other’s worst inclinations. I never realized just how many “bad norms” I had been accepting as legit until I finally got out of there.

  24. Chaordic One*

    This is not something I would have thought of or have ever run into, even when I was in H.R. Perhaps back in the bad old days of the Great Recession and trees were full of people looking for work a potential employer might have been put off by such a question, but they really shouldn’t be.

    I suppose that there is also a context to the question and that it might be more appropriate coming from someone who is experienced and who has a good track record of past work experience, as compared to someone who doesn’t have much work experience who is applying for a more entry-level job, but even then it shouldn’t be too surprising.

    1. Original Poster*

      Also, FWIW I am 30, and have a full resume from a prior profession I am looking to transition out of, as well as reasonable amount of non-paid experience in the area he was hiring for! So just like you said it shouldn’t be that surprising, but also, I am not like, a college kid just out of the workforce! He is just…gross.

  25. boop the first*

    On one hand, I love this idea. I would never be comfortable enough to cold call a random stranger, but I would love to have the chance to prepare applicants for whatever hellhole I managed to escape. There were so many times where a sweet person would walk in for training and I just want to grab their shoulders, turn them around, and tell them to RUN!

    On the other hand, this sounds a bit trickier logistically. Managers/owners come with an expectation of getting calls out of the blue. I don’t like the idea of former bosses giving my contact information to strangers. In fact, most places aren’t allowed to do this at all. I ignore all calls from my previous employer, so it might take a while to get my permission in the first place. this whole process sounds like it would be awfully drawn out.

    1. Original Poster*

      Totally – if he had explained that, but offered to reach out to a few people and put me in touch when one said yes, I would have thought that was super reasonable!

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