my awful former boss is my new coworker’s sister

A reader writes:

I’m a freelancer in a creative industry, and recently I’ve started a new project with a new company. The other night I was invited to their monthly team drinks as a way to welcome me aboard. One of the managers I was introduced to, Bob, said he had read my resume and had noticed I used to work for Company X. He asked me a few questions about working there — what it was like, who I worked for, and whether or not I enjoyed it. Company X is relatively well-known in our industry, so it made sense to me that he’d ask about my time there.

I said it was fine, and I really enjoyed the project I was on, but the company wasn’t the right fit for me and that’s why I had decided to end my contract. He kept pressing for details about it, so eventually I told him the truth: my manager there would regularly ignore calls and emails from the freelancers for weeks on end, which made us wonder at times if we’d been ghosted; we all had a lot of trouble getting paid on time; and there were even some instances of full-time workers being given credit for work I had prepared myself. I tried to handle the situation as best I could when I was there, but ultimately it began to impact how happy I was outside of work hours, so I gave notice. (I didn’t sound angry, just explained things factually.)

Bob seemed surprised but accepted that answer, and we moved on to another topic of conversation.

And then later on I heard from another member of staff that Bob’s sister actually works at Company X. I put two and two together and did some quick social media research and found out Bob’s sister is actually my old manager.

I feel like I’ve really put my foot in it now. I’m wishing I had handled Bob’s questions more professionally — maybe I should’ve just changed the topic of conversation? Even though I know I didn’t do anything wrong at Company X, I’m worried I’ve done something wrong in this situation. Do you think I should talk to Bob about what I said? Or just forget it all happened and hope for the best?

Bob is the one who should be feeling like he put his foot in it. Pushing for details about your experience there without mentioning that his sister is a manager there was a jerk move.

Frankly, even if his sister didn’t work there, continually pressing you for details that you were obviously not offering up initially was pretty rude. It’s generally understood that people often try not to badmouth former employers, and I don’t like that he kept pushing you to say more.

But more importantly, not mentioning that his sister was a manager there at the same time he was pressing you for details … that was a seriously crappy thing for him to do. If he’d said, “Oh, my sister manages the finance team over there, what was your experience like?” you’d presumably have given him a very different answer. And on some level he surely knows that, because there was a point in that conversation where it became weird that he hadn’t shared it … and that point was pretty early on.

Now, all that said, yeah, you probably said too much. Your initial (vaguer) answer was presumably the amount you were comfortable sharing, and you didn’t need to let Bob pressure you into sharing more.

But there’s also real value in people sharing information like “Company X doesn’t pay their freelancers without constant hassle.” And exchanging info about employers in your field is a key way people learn who they do and don’t want to work for or what landmines they need to watch out for. You didn’t say anything that wasn’t factually correct, and it doesn’t sound like you badmouthed anyone by name. You didn’t go on a hostile tirade; you were just matter-of-fact about the business problems you encountered.

That stuff is legitimate to share with trusted colleagues. It gets a little trickier with someone you just met, though. You didn’t yet know how Bob operates, if he had an agenda, or who he might be aligned with. With a new person, you’ve got to figure that anything you share could get repeated to anyone and decide if you’re okay with that possibility.

So: Is your discomfort about the possibility of what you told Bob getting back to his sister? Or is it more about the awkwardness of having criticized Bob’s family member to him?

If you’re worried about it getting back to his sister … it’s not ideal, but the stuff you said was factual and doesn’t sound like anything she should be surprised to hear. Maybe a little stung, but maybe it’s not a bad thing for her to hear people’s experiences working on her team. (If she’s both vindictive and influential, I’d be more concerned but since you didn’t note that she is, I’m going to assume she’s not.)

If your worry is more just that you criticized Bob’s sister to his face without realizing it … well, Bob created that situation and got the awkward moment he deserves. If you’d get more peace of mind by addressing it, you could go back to him now and say, “I just realized your sister works at OldCompany — you didn’t mention it when we were talking the other day.” See what he says. Or you could skip mentioning his sister entirely and just say, “I normally wouldn’t share that kind of thing about an old employer, and I hope you’ll forget I said anything. I really did enjoy the work I did there.”

But I also think it’s fine if you just leave things where they are.

Either way, I’d try to find some ways to be (a) scrupulously professional and (b) impressive around Bob in the coming weeks if you have the opportunity.

And either way don’t trust Bob going forward.

Read an update to this letter here.

{ 131 comments… read them below }

  1. Ann O'Nemity*

    I’d be so tempted to talk to Bob again! “Why didn’t you tell me your sister worked at Company X when you were asking me so many questions about my experience there?” Because seriously, why indeed.

    1. BenAdminGeek*

      Why indeed, indeed! It really has the feel that he was looking for the criticism of his sister.

      1. Not A Girl Boss*

        Right. I bet he knew exactly who LW was and that she had worked for his sister, and was data mining for said sister. In which case… he got what he wanted.

        1. EPLawyer*

          This. Sister has complained about the “terrible freelancer” she had. All Bob knew was his sister’s side of it so he was willing to find out how terrible OP was. Sister was expecting him to come back with “you are so right, entitled, attitude, everything you said she was.”

          1. Rose*

            You’re jumping to a lot of conclusions. Maybe the sister is upset she keeps loosing awesome freelancers and mentioned to Bob how upset she was OP left, and Bob decided to do some digging to help his little sis. We have no idea.

          2. JustaTech*

            Or Bob had heard his sister’s stories of “terrible freelancers” but doesn’t believe her because of [anything at all, back to when they were kids] and took an opportunity to independently verify his sister’s claims.

            Not everyone has a positive relationship with their siblings.

        2. RagingADHD*

          I seriously doubt that tracking individual freelancers from one gig to another, or discussing them by name, is on either Bob or his sister’s radar at all.

            1. The Man, Becky Lynch*

              It’s almost like we’re on a blog that often includes obscure work stories that tend to shock everyone because they’re so…wild and not the norm or something. Hm. Fancy that.

              So yeah, let’s just think everyone is out to get us because one boss ever demanded someone give their brother a liver transplant.

              1. HoHumDrum*

                I mean Sandangel didn’t say “from being on here we’ve learned all bosses are monsters”, they merely said “Yeah, we hope that’s not the case but having heard stories on here we know there are in fact some people out there who would act like that so it is possible” which IMO is a very reasonable point and doesn’t deserve the snark you’re giving.

          1. Rose*

            This is a weird reaction. It’s not like he had to stalk her. I managed two freelancers work streams, and I know exactly where they went when they left, like I know where any other coworker I worked closely with has gone. It hardly takes an interrogation. Asking where someone is going next is usually the first thing when someone says they have a new role, and obviously I know the name of my brothers company.

      2. Lola Banks*

        Not to speculate, but it seems like it could have been a weird, covert exit interview requested by the former manager.

      3. Mel_05*

        I don’t know if he was looking for criticism, but he clearly knew who she was taking advantage of that fact to find out more than he would normally get to know.

      4. JustMe*

        I’m betting his sister wants something from him professionally, so he wanted to hear about how working for/with her was without letting on about the relationship.

    2. DonnaMartinGraduates!*

      Noooooo… Too confrontational! Bob is sneaky. OP — take extra care whenever you engage with Bob, per Alison’s excellent final words of advice “And either way don’t trust Bob going forward.”

      1. MW*

        That’s exactly why she should flat out ask him why he did that the next time she sees him. To make it 100% clear to him that she’s on to his sneaky ass. Then Bob will know that the OP knows exactly what he did.

    3. Blue Eagle*

      I like the tone of the interaction with Bob from this comment (rather than Alison’s comment of “I really did enjoy the work I did there”). You don’t need to be defensive about what you said – he is the one who should be defensive about continuing to prod you without admitting his sister works there. In any event, I would not trust him with any other personal information going forward.
      One idea for future interactions of this type with other people, if they keep prodding you to tell them more and you are not really comfortable with it the best response is “why do you want to know that?” Then you can determine how to proceed based on what they say. If their response if “oh, just casual interest”, then your reply should be “there’s nothing more to tell”. And leave it at that. Someone a couple of years ago on this blog suggested that response and it has worked well for me so far.

  2. Pikachu*

    I wouldn’t bring it up again. Just because they are siblings doesn’t necessarily mean they have a relationship where they’d discuss it or bring you up at the next family dinner.

    It’s possible that he’s been hearing stories from her that make her look better while throwing her workers under the bus… making him surprised to hear from a neutral third party (you) that not all was what it seemed.

    Honestly I would not be surprised in the least to hear this type of feedback about one of my siblings! I still love them of course but I know they are not exactly professional and was actually terminated once for it.

    1. Michael Valentine*

      Yes, if someone told me my brother is a know-it-all intolerant doofus boss, I would not be surprised! He’s told me stories about work that don’t mesh with my own impression of him.

      1. Not A Girl Boss*

        I had that moment of clarity when my in-laws started complaining about the ‘entitled’ employees who were complaining about their business’ handling of COVID. Like, I’m pretty sure Alison would not side with you on that one, fam.

    2. Forrest*

      Yes, same here!

      And I actually have had an analogous situation years ago, when my then-boyfriend’s flat mate was complaining about how he’d had to miss class at university and now he had to go and explain why he’d missed X sessions to Dr MyDad, who was a total stickler and the least sympathetic lecturer he had, and I was like, oh, Dr MyDad is … my dad. To be honest, this didn’t particularly surprise me about my dad!

      My dad can be quite black and white about who is a someone he thinks highly of and who is a twit, and I think he’d be a nightmare to work with if he decided you were in the twit class. I’d never fish for details like Bob did, if someone unknowingly complained about him to me, I would not be the *least* bit offended or upset.

      1. A Library Person*

        I’ve looked up my father-in-law on Rate My Professor before, but what shows up actually fits pretty well with my impression of him! Learned a bit about his brothers (also professors), though…

      2. No I Can't Get You Out Of Detention*

        Feeling this. I moved to the school where my mom taught, and hoooooo boy.

    3. Dust Bunny*

      Seriously, if somebody told me that my uncle was an absolute ass as a boss and they got out of there as soon as they could, I wouldn’t bat an eye, because he was and anyone with any sense should have run, run, run.

    4. Willis*

      This is what I thought as I was reading OP’s letter. That Bob kind of knows his sister might be bad to work for and was trying to get info on it. I have a friend who I love dearly, but she is a very confusing communicator and I always wonder how it plays out at work. I wouldn’t be surprised to hear someone say they had difficulty working with her and wouldn’t tell relay the conversation to her. But…I also wouldn’t goad someone into talking about her. So, I agree to be wary of Bob, but I’d probably just let this lie.

      (And also, even if it did ‘get out’ that you said this, it just looks terrible on her!! Treating contractors poorly and not paying them is not really something I’d want to amplify if I was Bob’s sister.)

    5. Observer*

      The thing is that Bob kept pressing for information. So SOMETHING is up.

      But I still probably would not bring it up with him.

      1. Rachel in NYC*

        I kinda wondered if Bob’s sister/former awful boss had been looking to move to new company so Bob’s been wondering if it’s a good idea. Based on his knowledge of his sister, he may think she may not be the best employee but he’d never worked with her.

      2. Aggretsuko*

        Bob clearly suspects his sister is not all that and a bag of chips.

        That said, I would avoid talking to Bob if I were OP after this.

    6. alwayssunny*

      I was thinking something like this!

      I have a tenuous relationship with my mother. When I meet someone who may know her professionally, I don’t bring her up. I don’t want 1) someone to associate me with some of her problematic opinions, and 2) her to get wind that I’ve been in touch with a colleague (mainly because she’ll dig for information I don’t want her to know). I keep that information private to protect myself, I guess.

      Bob may have intended to be malicious, definitely. Or Bob may have been curious about his sister’s world and how she’s perceived by others? He definitely shouldn’t have pressed so strongly for info that the OP didn’t want to share forthright.

  3. I'm that guy*

    You should should probably take away from this is that Bob is just as terrible as his sister and you shouldn’t trust him as far as you can throw him.

    1. yup yup*

      Yes. The last line of the response is the most important piece of advice: don’t trust Bob going forward.

    2. RC Rascal*

      This. The sister is a jerk and Bob is a sneaky jerk. Both apples lay close to the tree. Bob is not for trusting.

    3. Where’s the Orchestra?*

      This was my primary take away as well. You gave the political answer, and he just kept pushing and pushing until you gave him details that you probably never would have.

      Trust him (Bob) about as far as you could throw him. And if you are into Scottish Highland Games, well, yeah, trust him less than the heaviest Caber you can pick up.

      1. HarvestKaleSlaw*

        To quote the late, great Douglas Adams: Trust him as far as you can comfortably spit out a rat.

    4. MCMonkeybean*

      Yeah, if Bob specifically asked who they worked for and then pushed for more details on why they left after they tried to be politely vague about it–it’s honestly hard for me to imagine anything other than Bob was hoping to get OP to say bad things about his sister! Seems like a family I’d want to avoid all around.

    5. allathian*

      Yeah, that’s my take on this as well. I’d be very careful around Bob in the future. That said, I might be tempted to ask him “why didn’t you tell me that your sister used to work at X company?” just to see his reaction.

  4. Ginger*

    So Bob and his sister work at competing companies?

    OPs situation is, I’m sure, not the first or last digging Bob has done.

    1. crookedfinger*

      Yeah, that was my thought as well. Now he’s armed with intel that his sister is a bad boss and might be having money trouble..

  5. Pyjamas*

    Bob prob knows his sis treats ppl like sh— I mean, acts like a jerk and that’s why he didn’t bring it up. It’s possible—no, probable—that sis badmouths the freelancers (in general if not OP specifically) and Bob wanted to hear OP’s side. He’s def sneaky but the jury is out whether he’s an ass

    1. highbury house*

      Yeah, the possibility that Bob and sis don’t get along is non-zero. Maybe he wants to poach her staff!

    2. Kiki*

      I’ve definitely listened to family complain about work situations a lot and then wondered what other folks they work with think. For example, my uncle complains endlessly about how difficult it is to work with his younger colleagues because “they don’t know the meaning of a hard day’s work.” I often wonder what his coworkers think of him because I suspect from their perspective he is the grouchy man who gets mad that male coworkers take time off to care for their children and thinks it’s reasonable for employees to fix office plumbing themselves (he had this whole rant about how his coworkers wanted to hire and expensive plumber but he just came in over the weekend and fixed everything himself. No, he does not work at a small business, he works at a large multi-national corporation who could definitely afford a plumber.)
      I wouldn’t do what Bob did because subterfuge isn’t a great way to start a good relationship with a new coworker, but I can see how maybe curiosity could get the better of him and he wasn’t trying to make OP look bad, just get more info.

    3. RebelwithMouseyHair*

      He is an ass. If he were fishing for ammunition against his sister, he could at least have owned up to it afterwards, on the lines of “I wanted to hear your honest opinion, so thank you for that. Full disclosure, that’s my sister you were working for and I now realise just why she’s having trouble keeping freelancer working for her! And I know not to put in a word for her with HR here.”

      1. The Supreme Troll*

        This is an important point that shouldn’t be overlooked. I would have trusted Bob (at least just slightly) if he showed honesty and been forthright about why he was asking these questions.

  6. BRR*

    I’d personally just leave it and basically pretend it didn’t happen. Mentally I would frame it as “what an odd thing for Bob to do.” And if Bob brings it up again I would still treat it as “what an odd thing for you to do.” I think this might be one of those situations where people take their cues from you and I would make sure Bob was getting that cue from me.

    I want to stress that you did nothing wrong here, but I would also suggest not going into such detail with new colleagues. Not just because they might be related to your former manager (WTH Bob), but I think while you’re building your reputation at this company it’s better to avoid going into detail about why you left your last employer, regardless of how professional you frame it.

  7. A. O. Nymous*

    There’s also the possibility that Bob doesn’t like his sister and wants to know whether her employees really like her as much as she says they do.

    At least, I have a relative who’s rather awful, who’s very kiss up/kick down (and we, as the family, are in the ‘kicked down’ group), and constantly brings tales of how good they are and how much their relatives like them to the dinner table. As well as tales of how they handled a situation with a subordinate which is when the other family members share looks of “That’s illegal” and “That’s inappropriate” and “That’s awful” and “How dare you”.

    While I wouldn’t be as disingenuous as to ask someone about their experience in that department of that organization without bringing up that my relative is its manager, I would definitely be interested in what Relative’s susbordinate’s have to say about them – and I’d probably be more disturbed by their subordinates singing their praises than by a factual or even highly emoted account of how terrible it was.

    1. A. O. Nymous*

      “How much their relatives like them” should be “How much their upper managers and same-industry-different-company peers like them”

    2. juliebulie*

      It’s funny, but that was the first thing that crossed my mind. That Bob was skeptical of his sister’s stories and was trying to get another opinion.

      1. Archie Goodwin*

        Honestly, that was my own impression, too, for one reason or another.

        I mean, he went about it in a colossally bad way, but still.

        1. Oof*

          Me too! Or not even that there were stories from his sister. I have never heard my brother speak on his past colleagues, but I would be super curious if I came across someone that worked with them. Because he is one horrible person, but he can also be quite charming. I’m positive that I would do so in a better way than Bob, but I’m human. The best of intentions can be lost to the curious cat!

          1. MCMonkeybean*

            Yeah, I mean who doesn’t love hearing dirt about their siblings? But that was a tremendously crappy situation for Bob to put the OP in. Really, really not okay.

      2. Where’s the Orchestra?*

        If this was Bob’s goal, well, the goal isn’t horrible but his method of getting the information he wanted seems underhanded and can lead to employee trust issues.

    3. Dust Bunny*

      Yeah, I wonder if Bob has endured endless hours of kvetching from his sister about how useless her freelancers are and was already beginning to suspect she wasn’t telling the whole story. I have friends and family I love but whom I would never want as bosses/coworkers/spouses/other high-stakes relationship.

    4. Pikachu*

      “Kiss up/kick down” is a fabulous way to describe that dynamic. Can’t believe I’m hearing it for the first time.

      1. A. O. Nymous*

        It’s also been called suck up/kick down, but that lacks alliteration as well as the picture I’m imagining, of a pyramid or ladder where a person in the middle is kicking the person below them while kissing the rear end of the person above them: that doesn’t really work for sucking up.

        1. Cedrus Libani*

          Germans call such people “bicycle riders” – when viewed from above, their heads are bowed, but when viewed from below, they are furiously kicking. Always liked that one.

  8. A. O. Nymous*

    “How much their relatives like them” should be “How much their upper managers and same-industry-different-company peers like them”.

  9. Colleague’s Dog’s Viking Funeral*

    I had a similar experience one time.
    sitting with a friend minding my business, when we are asked if we know Uniquefirst Unique Lastname.
    friend says no, I say I know who she is.
    “Do you like her?”
    I don’t know her.
    “Do you hate her?”
    I don’t know her.
    Come on, you can tell me, do you hate her?
    No. Why are you asking me this?
    “She’s my sister.”
    Oh, that explains why you, a clearly preteen girl asked my friend and me, clearly teenagers, while we were walking through the park, if we knew another girl who was around our age and who we probably went to school with.
    Because it would be funny if we’d said yes.
    Because you are 10 years old.

    1. Reba*


      Regardless of Bob’s motives or foreknowledge that we are speculating on in the comments, he just doesn’t come out looking great here.

      1. Where’s the Orchestra?*

        Agreed – his methods of getting the information he wanted were far from excellent.

        I would think just asking for any process improvement ideas may have dissed out some of the same issues he got his way – but wouldn’t damage trust the way he did.

      2. Colleague’s Dog’s Viking Funeral*

        yeah, Undercover Boss at least would have given OP a car or something. This was just a jerk move.
        OP, put the discomfort where it belongs, on him.

  10. DonnaMartinGraduates!*

    I really love how thorough and practical Alison’s advice is here. This is such an interesting (and perhaps common) situation for someone to find oneself in, and I can imagine feeling nervous and concerned I might have said too much. (It does appear that OP stuck to the facts.)

    Alison has parsed out the minute nuances of the whole scenario and it’s obvious he pressed for more details than you normally would have shared. Sterling advice, too. Definitely would watch out for this guy — you don’t know what kind of relationship he has with his sister, nor if he has an agenda.

  11. caradom*

    I’m sorry to say that Bob’s sister will have put this up to him. That is why he pressed you whilst intentionally never telling you who his sister was. Right now, record all the details: the party, his management position, the time it happened, exactly how the convo went (how many times did he push you, twice? Five times?). You are perfectly right when you say it is completely normal for a manager at your new workplace to ask that )so it’s not like you did anything to encourage the conversation). This might be nothing but you can’t rely on retrospective memory if something happens and if it ever became a case you will be weaker without recorded instances).

    You said he is one of the managers – I’m hoping not your manager / direct manager. Do NOT say anything, because Bob and sister will discuss it and she will convince him to escalate. However, find a discreet device where you know how to press record (this isn’t a legal thing, it’s something that can be useful in other ways if something happened. Think social media).If something happens press record, then find a discrete device with video recording as well. Again, don’t mention it to anyone and don’t think you can use it as evidence (you can find out about those rules if you are interested for where you live).

    1. Susana*

      It’s indeed legal if you are in a single-consent jurisdiction. Meaning you can record your own conversations without your fellow conversant’s OK. (you can’t record the conversations of others if you are not part of it)

      1. caradom*

        I know it differs by states so that’s why I said the bit about the legal stuff. But that is very interesting to know, thank you!

    2. Carefully*

      Be very careful before deciding to record clandestinely. In some states like California, it is a CRIME to record without consent of all parties present.

      1. caradom*

        I never suggested using it legally. Posting it on all outlets of social media using a dummy account is a completely different matter. No one can prove it ….

        1. The Gollux, Not a Mere Device*

          One of the lessons of the recent news has been that there’s a non-trivial chance that someone can connect people to “anonymous” posts. And they don’t have to prove it in order to fire you for it — “person suspected of making an illegal recording” isn’t a protected class/status.

        2. Where’s the Orchestra?*

          Putrid idea.

          I always get amazed when I hear about secretly recording, it’s just so underhanded. Most people don’t realize that “The Prince” by Machavelli was Satire (like the great majority of his works). It was meant as a warning, a guide of what not to do if you are in power. They take it literally, and so many situations are the worse for it. Point of this is, well, the ends never justify the means. Do things the right way.

        3. Metadata minion*

          Even if it weren’t relatively easy to trace this kind of thing digitally, if you’re talking about recording someone in a workplace, there are only so many people who it could possibly have been! Gee, who could it be posting this recording of a conversation between me and someone else when I know it wasn’t me?

  12. Mavis*

    My mother was a teacher at my rival schools growing up. I learned early and often not to say, “Do you know Mrs. Mavis?” because that invited unpleasant opinions on her – “Yes, I hate her” – and when they asked why I was asking, I got to awkwardly say, “She’s my mother.”

    Instead, I started saying, “My mother teaches there – Mrs. Mavis, 8th grade English,” and the person I was talking to could bite back any mean thoughts about her and just say, “Yes, I had her last year,” or whatever.

    1. Colleague’s Dog’s Viking Funeral*

      Well done and very astute young you.
      I’m sure many times the kid said, “I hate her” was really looking for a way to connect, and had a fifty fifty chance. “oh, this kid must know her. I’ll say I hate her, cuz that will be cooler and I’m funnier when I’m being mean.”
      So yeah, take the chance out of the equation.

  13. Observer*

    And either way don’t trust Bob going forward.

    This X 1,000

    Bob pulled a nasty move on you.

    Is his sister still there?

  14. Rich*

    There’s no point in talking with Bob. He’s already proven to be shady in how he handles this question. If you can’t trust him on this (and you can’t) he can’t say anything to improve your current understandable concern. Any “no, it’s fine” will be covered in doubt, when he’s already shown a sneaky manipulative side.

  15. Where’s the Orchestra?*

    Collecting all my thoughts in one place.

    There is some merit to the idea that Bob wanted a completely unvarnished opinion of his sister as a manager, but his method of getting that unvarnished truth is just putrid. OP probably rightly doesn’t trust him at all, and honestly he looks no better than his sister as a manager now.

    Doing the right thing the wrong way is still wrong most of the time in the end.

    1. Colleague’s Dog’s Viking Funeral*

      I agree, particularly with your last sentence.
      Bottom line, Bob can’t really get what he wants here, doing it the way he did.
      If he wants an honest opinion, he should be honest.
      No, it will not be unvarnished, but he can use his knowledge and experience to figure out nuance.
      Or, if he or his sister want unvarnished, then do an actual anonymous survey, don’t ambush random people at cocktail parties.
      And really, why is Bob so invested in his sister’s career?
      They work at different companies.
      If you want to bring an outsider into your weird work synergy sibling thing, disclose that.

  16. Phil*

    Bob sandbagged you, which doesn’t endear you to your poker buddies and even less in the workplace. But on the other hand, you learned something vary valuable about Bob. So over all, I’d call it a win.

  17. Susana*

    Honestly – I get why OP feels awkward. You never want to feel like you’re bad-mouthing someone’s sibling. But *he* pressed you for details and you gave just the facts, ma’am. As a former freelancer, I’m thinking maybe it’s good for her to realize that freelancers talk to each other about who treats freelancers badly, doesn’t pay on time or at all, etc. Reputation matters. That’s why you left them, and now sister can’t lie to herself about why.

  18. voyager1*

    I am not sure why LW feels like she did something wrong here. If what she told is true, so be it. If it hurt Bob’s feelings, well… too bad so sad.

    Lesson for Bob, don’t ask questions you aren’t going to like the answers to.

    LW you didn’t do anything wrong and shouldn’t feel embarrassed in anyway.

    1. GemmaBeth*

      I understand feeling awkward, I would too, but I agree it’s not on OP. For that reason I would either use the first phrasing AAM suggested, about “why didn’t you mention your sister…” and return awkward to sender, let him explain himself a little, or I wouldn’t mention it at all. I wouldn’t use the “please forget I said anything” phrasing because it sounds like you’re apologizing or admitting you did something wrong and you didn’t.

    2. Elspeth McGillicuddy*

      It doesn’t sound like his feelings were noticeably hurt. Maybe he has a good poker face, or maybe he’s hated his sister since grade school and is privately delighted that she has a bad rep.

    3. Generic Name*

      I agree. What you said was entirely factual and if it reflected badly on Bob’s sister, that’s on her. I feel like it’s pretty normal for contractors to note who doesn’t pay when talking shop with others in the industry for example.

  19. Regina Phalange*

    I once had a friend who had just started working at a real estate settlement firm that my mom, a realtor, did work with. I went to pick friend up for lunch at her office, and when she introduced me to one of her new co-workers, Nina, I said “Oh, do you know ‘Samantha Jones” to which she replied, “You mean Samantha the Bitch? Yes, she’s always calling here asking us to hurry up and write checks” (you know, the money they owe the realtors). I was too stunned to say “that’s my mom” because who would have expected that answer? I obviously know her if I’ve asked you that question! Anyhow, I ended up telling my mom the story. Mom calls her the next day and says “Hi Nina, this is Samantha Jones, you know – Samantha the Bitch” and proceeded to tell her I was her daughter and also, it was her job to pay people on a timely basis. I would have paid money to see Nina’s face! (and maybe I should not have shared the story with mom, but I was all of 19 years old and it seemed like a good idea!)

    1. Mel_05*

      Wow, it’s so strange that, that would be her immediate response! I’ve certainly complained about coworkers, but I’m pretty careful to be sure I’m complain to friends who have no connection to them!

    2. There's probably a cat meme to describe it*

      Just… *chef’s kiss*

      It helps that I could totally picture Kim Cattrall as your Mom delivering that line. Nina sure learned something very valuable that day!

    3. allathian*

      Thanks for the laugh. I do hope Nina learned not to badmouth her boss when someone asks if she knows her…

    4. Regina Phalange*

      I can’t recall if my mom went above Nina’s head to complain about here, but I don’t think so …. I’m pretty sure she got her checks quickly after that! I do know Nina tried to make my friend feel bad, like it was her fault that she immediately answered my ‘do you know’ question w/o considering why I might be asking. And now that I think about it, I’d still tell my mom if that happening today–if it were a comment based on a legit grievance, I might keep it to myself, but since it was really a reflection on Nina’s behavior, lack of filter, and lack of work ethic, she pretty much deserved it!

  20. Aggretsuko*

    This reminds me of the time in college when I was an English major and the guy I was on a date with asked if I’d heard of Professor X. I said I had and hadn’t heard good things.
    “That’s my aunt.”

    I did eventually meet the aunt at some party or other, she seemed nice there, but I avoided taking any classes with her since I was with her nephew for awhile before breaking up.

  21. RagingADHD*

    You didn’t say anything untoward or unprofessional. It’s an awkward moment better left in the past.

    I once had a trainer in a professional certification program name-drop one of the professors in the same department where I got my undergrad degree – did I know the guy, etc.

    I said I’d never studied with him, but had friends who did, and he left quite a reputation in his wake – dismissed for sexually harrassing and verbally abusing his students.

    The trainer bristled a bit and said, “He’s a good friend of mine!”

    There was really nothing to say but “Thanks for letting me know.”

    Maybe Bob is a jerk and likes to play mind games. Or maybe Bob knows his sister is a crappy manager and doesn’t want the guilt-by-association.

      1. There's probably a cat meme to describe it*

        I wanna guess probably knew about it? But ‘it’s all lies and exaggeration’ and ‘it’s so easy for women to accuse innocent men of anything these days’. All the usual gymnastics to avoid facing uncomfortable truths.

      2. RagingADHD*

        My impression of the trainer was that he shared his friend’s proclivities and considered the behavior normal. Of course, he didn’t have a position of power over anyone, and that’s probably a good thing.

  22. Not So NewReader*

    OP, add my name to the list of people here who if they had to work with certain family members then they would just get a new job.

    Bob might be one of those people who would quit rather than work with his sister.

    None of it really matters because it sounds like what you said was factual. We can’t and shouldn’t protect people from their own selves. This means if a manager is a poor manager it is NOT on us to put a public happy face on all the BS.

    I haven’t seen reference to the trend for a while now, but years ago companies were cautioning their employees regarding how they treat subordinates. The problem they were trying to address was grapevines in the community surrounding the company. If a company is toxic it can go right around the community with word of mouth. If your old boss is concerned about how people talk about her and the company then maybe she should start playing a clean game. Just saying.

  23. AKchic*

    Bob brought this on himself.

    Bob’s actions are highly suspect and he isn’t someone I’d be trusting. Be 100% professional, but do not trust him. 1) He does not accept boundaries; 2) He is related to a former, horrible boss; 3) he hides the fact that he is related to your previous, horrible boss while trying to get dirt on your last job and aforementioned horrible boss.

    Whether he was trying to gauge your character in contrast to what he’s heard from his sister, or trying to gather dirt for his sister, I think we need to look at it this way: He has had time to look at OP’s work and personality for himself and make his own determination of OP’s character. He could have been “above board” and been honest about who he was in relation to the previous boss and been open about *why* he was asking. He chose not to. Deception does not breed trust.

  24. staceyizme*

    It’s an interesting paradox! You’re being pressed for information by someone who is pressing you to share while concealing their own relationship to the situation. Unfortunately, the “cat is out of the bag”, but you’ve got nothing to gain by pursuing it further. Mr. Crappy-Maneuver has given you a little insight into his own operating style and you’ve received a refresher course in “no, I don’t think that I WILL share that with you… I don’t know you that well”.

  25. EvilQueenRegina*

    Not my story, one I’d read online in a post about interview horror stories, but it was relevant to this post:

    So a candidate goes to an interview, and the interviewer says “So, I see you work at Company X. Do you know someone called Fergus Smith?” Candidate works in a different department, but knows who Fergus Smith is and can’t stand the guy. He tries to dodge the question by saying something like “I know who he is, but we’re not in the same department and I don’t know him that well.” Interviewer starts talking about how this person is an a$$hole, and candidate eventually says something like “I had heard he can be a bit difficult to work with, but I hardly know him.” Interviewer keeps pushing it, and eventually the candidate admits “Yeah, he’s an a$$hole.”

    Interviewer immediately throws out the candidate’s CV, saying “Never insult a colleague in an interview and never say it to their brother in law!”

    1. Cedrus Libani*

      TBH it sounds like that brother-in-law fits right in with his new family; the candidate dodged a bullet. Can you imagine having that guy as your boss?

    2. Where’s the Orchestra?*

      Eesh, I’d call that a bullet dodged. Just like Bob in the letter the interviewer kept pushing until he got some predetermined answer that was wrong.

      I said it elsewhere: the ends don’t justify the means; or doing the right thing the wrong way will just lead to the wrong results.

  26. Reluctant Manager*

    I try to remember that, “Why do you ask?” Is useful for stalling as well as information gathering

    1. RebelwithMouseyHair*

      yes, this! Making note for future reference, because I’d want to curl up and die if this happened to me.

  27. _ID_*

    As noted above, Bob is a douche canoe. There’s a reason he was pushing for more info. We don’t know that reason yet – but he has shown himself as someone to NEVER be trusted.

    One thing I learned the hard way in my career is to keep negative opinions strictly to myself unless I’m with trusted friends. Rarely do co-workers meet that criteria. I’ve been burned a few times in my youth and realized that my own big mouth is to blame. I live in a city where most residents of any long standing probably have 1-2 degrees of separation from anyone else. So, when pressed by a Bob-like cretin, I’m super vague. “Oh the people there are great!” Or “they are so customer-focused”…etc. Find something good to say and refuse to go beyond that. Good luck, OP and watch your back around Bob!

  28. Freelancer*

    As someone who works in a freelance creative industry too (I wouldn’t be surprised if it was the same one), I don’t think there’s anything wrong with what you said or did. You talked about factual, concrete reasons why you had a negative experience – you didn’t say anything personal about your manager, and you listed things that your previous company should be embarrassed about, not you. And – in my industry at least – it’s pretty common to speak quite candidly to co-workers about your negative experiences with companies and managers to warn people from working with them (if they can avoid it). I’m sure Bob expected you to complain about his sister as a manger, and was just surprised when he heard about all the other administrative reasons you had a bad experience with the company itself!

  29. Skytext*

    One thing that wasn’t addressed in the answer and I think it’s worth mentioning: this didn’t happen in the middle of the workday in the office. In that situation it is much easier to keep your professional hat on and guard your words and thoughts. It happened at an after-hours social gathering where drinking was the whole point. Alcohol is notorious for lowering the inhibitions and loosening the tongue. Don’t beat yourself up OP because you let Bob goad you into saying more than you were comfortable with.

  30. Castaspella*

    I used to work at a call centre where there was a referral scheme, so people used to get jobs for friends and family members. One of the supervisors got a job for her husband on a part time shift and when he first started, he would sit in the break room and chat to whoever was in there, and ‘casually’ ask them what they thought of that supervisor Gill without identifying himself as her husband. She was quite hard work (erratic, short tempered and impatient, all fine supervisory qualities…) so there were a couple of people caught out by this. Once they’d disclosed it he would then almost triumphantly reveal who he was. You know it all got back to her. It was never clear whether she sent him on his little fishing mission – I wouldn’t put it past her – or if they were both just a pair of snakes.

  31. Anya Last Nerve*

    I’m trying to understand the concern with the e-cigarette letter. I thought the whole point of e-cigarettes and vapes is that there is no second hand smoke because…no smoke? I get that smoking then in your area is illegal but especially considering OP isn’t even in the office, this seems to me to be similar to using space heaters in the office even when they are against the rules (which I have done in some cold offices).

    1. Metadata minion*

      There is still vapor, which contains things ranging from carcinogens to volatile oils that are harmless but which will make the whole office smell like happy strawberry vape liquid or whatever.

  32. New Mom*

    This reminds me of one of my cousins, who is not a very nice person. Years ago I went to a graduation party for a friend. The next day my cousin, Wakeena, called me out of the blue. I couldn’t remember the last time she had called me, and she asked how I was. Then she asked me about the graduation party. I assumed she knew the person. She asked a few questions including if there was a DJ there. I replied there was. Then she asked if the DJ was good. The DJ had refused to play a few songs, which seemed weird for a graduation party so I said he wasn’t great, and then she started laughing and talking to someone else who was apparently on speakerphone with her… the DJ.

  33. learnedthehardway*

    The person I would bring this up to (if I brought it up) would be my current manager at the company you are now working with. I’d tell my manager that an uncomfortable situation came up at the event, where an employee really was digging into the reasons why I’d left the previous company, wouldn’t take a diplomatic answer, and that I was ultimately honest and factual, and then later found out he was the sibling of my former manager. I’m now worried this information will be held against me, and felt that I had better tell my new manager about it. I’d ask if my new manager has any advice on what to do, and would tell the new manager I don’t intend to confront Bob about it, but did want NewManager to know.

  34. Kittenthatmoos*

    Bob was definitely being shady, but I disagree with Allison’s statement that you shouldn’t share that kind of information with anyone. That feels like a way for bad companies/managers/etc to dodge responsibility for their actions or keep an undeserved reputation. When I was interviewing after I left a toxic job, I started with “it was a bad culture fit” but many pressed for more details as to why it was a bad fit, which made sense since culture is a broad term. I wasn’t going to lie to them about the way my manager treated me. I was matter of fact about the issues I faced and what I wanted out of a new role due to those experiences. I didn’t want to end up in another role just like it and providing some more details helped us all gauge if I would experience the same issues here. To me, it’s only badmouthing if you are sharing opinions and not facts.

      1. Kittenthatmoos*

        From Allison’s response:
        That stuff is legitimate to share with trusted colleagues. It gets a little trickier with someone you just met, though. You didn’t yet know how Bob operates, if he had an agenda, or who he might be aligned with. With a new person, you’ve got to figure that anything you share could get repeated to anyone and decide if you’re okay with that possibility.

        Normally the people you’re interviewing with for a new job are not people that you know. I know that’s the case for almost all of my interview (not promotions). My disagreement probably comes from the fact that I don’t care if my comments get back to my old employer.

        Mainly my comment was pushing back on the idea that making factual, but unflattering statements about an old job is something that should be avoided at all costs. If you personally are not comfortable with it, that’s fine, don’t do it. But those of us who are comfortable with it, we shouldn’t be penalized socially for talking about our experiences.

        1. Ask a Manager* Post author

          But then you don’t disagree. I wrote, “With a new person, you’ve got to figure that anything you share could get repeated to anyone and decide if you’re okay with that possibility.” You can decide you’re okay with it, as you have. The OP was not.

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