my former boss won’t leave me alone

A reader writes:

I currently have a full-time job as a manager in an industry that is a very small world. I’ve worked here for three years, and I love it. My question concerns a boss I had at the previous company where I worked, Bob. He wants to stay in touch. I don’t.

When I worked for Bob, I got promoted multiple times and eventually became his second-in-command. But he wouldn’t relinquish any power to me, instead always asking for my advice and never taking it. I found the position extremely frustrating. It felt like a waste of time, plus I wasn’t learning anything.

The company had multiple under-performers, but Bob wouldn’t fire anyone. He always wanted to be liked. Even when serious behavior issues arose, including racist and sexist comments at work, he would let it fester rather than disciplining or firing the offender. (Example: One employee made inappropriate jokes about child sexual abuse material at work. Bob told me, “His wife just had a baby! I can’t fire him!”) Several talented female employees and employees of color quit the company over Bob’s behavior. This company did have an HR department, but Bob would always pressure people not to make official reports to HR, claiming he would handle disputes himself – which he never did.

After getting a much better job, I’ve realized just how much Bob failed me and my colleagues. But because I ignore his texts, he has started talking to other people I know – including my current coworkers and boss – about how I’m “ignoring him” and he’s sad. Again, because my industry is small, I will most likely run into him at conferences someday, which I’ve avoided due to pandemic cancellations but soon won’t be able to avoid anymore.

I think I have a few options:

• Continue to ignore him. When coworkers/peers tell me he’s asking about me, keep shrugging it off and saying we simply lost touch. I’m not sure how to keep this up if I run into him at a conference and he asks me outright if I’m upset with him, though.

• Send him an email apologizing for ignoring his texts, explaining that I needed some space to mentally regroup/adjust to my new job. This would also require me to respond to any future contact and to generally pretend I still like him.

• Send him an email explaining that I feel like he failed me as a boss and that I wish he would make some changes to how he manages other people, especially since he is currently still a manager. I know that this would upset him greatly, due to his need to be liked by everyone, but he is already upset that I am ignoring him. Sending him a message like this might end our relationship (what little is left of it), but it also might lead to further problems, such as him continuing to complain to my current boss/colleagues/peers about my decision to cut ties.

I’m worried my coworkers think it’s weird that I don’t talk to him. I have explained the full situation to my boss and he seems understanding, if a bit confused by how firm my decision has been to cut off a former boss in a small industry like ours (I have a good reputation with my boss thanks to my past three years of good work at this job, which probably helps). With my other coworkers, I have not really elaborated on any of this, although naturally they are curious.

I don’t think sending Bob a message about his failures as a boss will result in much meaningful change to how he functions as a manager. If it were that easy to get managers to change, there would be far fewer bad ones. People aren’t usually bad managers because no one has ever told them things like “you shouldn’t let behavior problems fester” or “you can’t allow racist and sexist comments at work.” They’re bad managers for much more complicated reasons — in a case like Bob’s, probably some combination of a deep-rooted fear of upsetting people or being disliked (the terribly irony of which is that it nearly always leads to the manager being disliked by their best employees), bad priorities, incompetence, and insufficient oversight from above him. You can’t fix any of that with an email to Bob.

I do think you can just continue to ignore him if you want. If you run into him at a conference and he asks outright if you’re upset with him, you can say, “I’ve just been incredibly busy and terrible about keeping in touch— sorry about that!” That may or may not be credible, but it’s a thing you’re allowed to say and he can’t really insist that it’s not true. (Or rather, he could but that would be extremely weird and you could stick to your story and then quickly excuse yourself.)

The easier option, though, especially since he’s complaining about your lack of response to others, is probably to respond to one of his recent messages. Don’t respond immediately; let it sit for a bit and then respond by saying, “Sorry for the long delay in responding! I’ve been incredibly busy and terrible at keeping in touch. My schedule won’t calm down for the foreseeable future but I hope all is well with you!”

Frankly, if you wanted to, you could even say, “I’ve been hearing from colleagues that you’re worried that I’m ‘ignoring’ you. I’m just really busy and I hope you will stop saying that to people since it’s making it sound there’s drama when there isn’t. Hope all is well and I’ll see you at (conference)!”

You could also choose to just have the bare minimum amount of contact with Bob to stay on good terms, given the small industry — meaning you respond to the occasional message (but not all) with something cheerful, vague, and brief. Sometimes it makes sense to do that for political reasons, although I can’t tell whether or not it’s the case for you (and if you can’t stomach it, then so be it).

But also, you can just keep ignoring him if you want, and shrugging it off (“eh, we lost touch”) if anyone asks you about it. It doesn’t need to be a big deal to you just because Bob has turned it into a big deal for himself.

Read an update to this letter. 

{ 200 comments… read them below }

  1. Addison DeWitt*

    I wouldn’t “hear from colleagues” anything. I would ignore him, not even remember he exists, and if he mentions it at a conference, then “Well, new job, so many things to do, good to see you!” Give him nothing to grab onto and no intimation that you’re ever going to be closer– indeed, that he has anything to do with your current life. Because he doesn’t!

    1. The Person from the Resume*

      I’m am tempted to suggest blocking his texts because there’s less cause for the LW to think about it.

      However the main issue seems to be now the LW is hearing from current colleagues and friends that Bob is saying she’s ignoring him which is just so wierd.

      1. Smithy*

        I’m not in a small industry – but it’s certainly a gossipy one. So talking about where former colleagues are and how they’re doing isn’t uncommon. In that vein, I have former colleagues (from even longer than 3 years ago) who I’m in touch with who’ll ask me about other colleagues who I’m not in touch with.

        It can certainly start innocently enough in terms of catching up – and as with all things social media – seeing notifications on LinkedIn can help instigate that nostalgia chat “Oh did you see XYZ got a promotion/is speaking at blah/made an odd post about their mud bath retreat and/or crypto”. So if anything, I flag this more as a note of it not being strange unless it’s happening a lot. Like if peers are noting it happening weekly, that’s a lot different than at a quarterly happy hour.

      2. Hannah Lee*

        Rather than blocking, depending on what phone/service LW has, they may be able to set up a Bob subfolder, so all his texts land there and aren’t popping up in their messages at random times.

        Then, when LW feels like they could deal with a bit of Bob, they could look in the folder and pick one thing to respond to.

      3. Not Tom, Just Petty*

        Except Bob wants everyone to like him. Being ignored means OP might not like him. Bob needs to tick “OP still likes me” off his list. It’s rather sad. But not OP’s problem.

        1. Princess Sparklepony*

          Not Tom, Very much this! Bob’s not going to give up because he has to WIN that Like. He will keep pushing to get OP to like him again. OP is in a tough spot because of Bob’s issues.

          Might be good to do the slow return of every 5th text then space to 6 or 7 and keep increasing the length. If OP sees him in person – Oh gosh, so very busy, etc.

          Since it’s a small industry according to OP, I’m surprised word hasn’t got about about Bob being a bad manager. But I’m guessing that he’s one of those nice guys (who aren’t really that nice) who is very pleasant in a superficial manner but knows how to sell the nice. So people think he’s a great guy until he’s their manager. Plus the people who he shields think he’s the best guy ever.

    2. Sparkles McFadden*

      Yes, agreed. When colleagues mention “Bob is sad you’re ignoring his texts” you can respond “Wow, that’s pretty weird Bob would do that” and move on to something work-related.

      At conferences, say “Good to see you. Things are so busy these days!” Then find someone across the room you just have to talk to.

      If you try to explain why you’re ditching Bob, you’re going to make Bob’s unreasonable behavior seem reasonable.

      1. Rainy*

        Yup. What Bob is doing is mobilizing flying monkeys, and the best way to deal with flying monkeys is to say “wow, such a weird thing for Bob to say!” and change the subject.

      2. GammaGirl1908*

        The more you try to explain, the more people think you are giving them openings to convince you. Give the most neutral minimum you can. All fine, busy with new job, must fly, ta-ta.

        This guy thinks that as long as LW stays in touch, then they are “friends,” and so working with him must have been fine (and thus he is a Good Person* ™). The neediness is the anxiety that LW might be upset with him (thus making him not a Good Person ™). That’s all his burden to manage. As long as LW is not, like, actively hostile toward him or running around badmouthing him, she doesn’t owe him anything more than basic politeness and neutrality (if that. She would be within her rights to, y’know, tell the actual truth).

        *the Good Person is a close cousin of the Nice Guy ™.

        1. Rainy*

          I dated a dude who engaged in the romantic equivalent of this behaviour–he *desperately* wanted to remain friends with me after I dumped him for cheating, because if he could tell himself we were friends, he didn’t have to examine his own terrible behaviour.

          I cut contact with him and if I saw him in public, I gave him the cut direct, and it was so upsetting to him that eventually he sent me the world’s worse fauxpology email, to which I did not respond but which upset me all over again until a friend’s roommate performed the email poetry-slam style. :) I really cannot recommend enough this method of taking the sting out of clueless people’s malign communications!

          1. 2 Cents*

            Ooo, I’m imagining that email slam! Have you ever seen Michael Shannon’s dramatic reading of this over-the-top sorority letter? Google Michael Shannon Reads the Insane Delta Gamma Sorority Letter — warning NSFW

            1. I have RBF*

              Holy cow! That’s hilarious! That letter was bananapants, and the dramatic reading was funny as hell.

            2. Princess Sparklepony*

              Why is there not at least a like button? That would deserve a Love button.

              I want to see more of Becca’s emails read by Michael Shannon. I’m guessing this isn’t the only one that is out there.

          2. MigraineMonth*

            I dated a guy for two months before I broke it off because he was so insecure and jealous. For the next 8 months, he sent me messages accusing me of having cheated on him, demanding that I not contact him, and also whining about the fact that I hadn’t responded to his last message.

            I should have blocked him, but it was too funny. A poetry-slam of those messages would have been amazing.

            1. Rainy*

              Hopefully it makes up for the massive deductions for typoing “worse” for “worst”, which bugs me when other people do it! My kingdom for an edit button!

              1. DJ Abbott*

                If you are using text dictation, it wasn’t you. My iPhone does that all the time. The last update made it unable to understand plurals and the endings of words, among other things.

              2. Princess Sparklepony*

                I blame my autocorrect which actively works against me. It really hates me. It’s changed the entire meaning of a sentence and then I forget to proofread, but I still blame autocorrect. Especially when I put in a perfectly good word that is spelt correctly and then I see it posted a totally different word that it decided was a better choice!

          3. Caliente Papillon*

            That’s hilarious! But also exactly what I was thinking re: OP if this were some person you dated doing this would you think you should call them? The answer is no, though I know some people would because some people just cannot handle not appearing nice. Yet it’s not mean to remove yourself from a relationship of any kind if you want to. You are not obligated to entertain Bob or appear like X for Bob or make it alright for Bob. Bob is a jerk who lets people be egressed against AT WORK. Bob sucks and has no integrity yet Bob wants to make you do things for him.
            Also Bob is juvenile AF going around whining to everyone about how OP doesn’t want to talk to him.

          4. crisper*

            Ooh, I wish I could have heard that! I once performed as “found poetry” the increasingly unhinged text string from a guy who I told I didn’t want to date anymore. (Not the “you failed by not having babies” guy I mentioned in another post’s comments… he was totally cool about my moonwalk out.)

          5. JSPA*



            A. You don’t need references from an ex

            B. It’s not unusual to cut contact with an ex, whether or not they were horrible

            C. Being an openly bad manager and being a scheming, cheating, lying partner are not the same thing.

            “I am flooded with new appreciation, all at once, of how much better you could have been” is the only point of similarity. But, “I put up knowingly with overt bad management” is something OP can investigate more fully on their own, without pointing it all the the ex-manager.

        2. rebelwithmouseyhair*

          Not only does he see OP as a friend, he probably sees himself as her mentor, the guy under whom she blossomed and thrived and rose to become his second in command, so he’s probably thinking she’s being ungrateful too.

        3. Blackcat*

          Yes, I’m sure this is it.

          I have a similar dynamic with a former toxic supervisor.

          She wants to be friendly with people she’s harmed so she can pretend the harm didn’t happen. She *knows* what she did was bad, but she’s lying to herself about it. The fact that none of her former reports speaks to her drives her nuts (according to the few still there).

      3. Cedarthea*

        My father has always said “your friends don’t need an explanation, and your enemies won’t believe you anyway” when people start over-explaning or rationalizing things.

        In your example if these other people are your friends they don’t need you to explain why you haven’t responded to Bob and if they are your enemy there is no explanation that will suffice so why bother.

        1. Smithy*

          I think this is particularly true in a work context. In the same way that AAM said there are no simple reasons why people are bad managers, there are usually no simple reasons why or how people stay working for or with bad managers.

          A very simple explanation for how the OP is hearing that her boss is bemoaning the lack of contact is that the OP has stayed in touch with some people that Bob still manages or works with. And for those people, they find it either easy for their work-life or beneficial for their work-life to engage in some kind of conversation about the OP. Either conversation they contribute to (i.e. proactively mentioning they’ll see the OP at a personal or work event, or just saw them at either) or answering truthfully if asked by Bob (i.e. did you see OP at the Monthly Industry Round Up?).

          Again, simplest answer is it contributes positively to their work life. Even if it may make Bob upset at the OP, being seen as an “industry insider” who knows “all the gossip” can easily help you with different bosses. Let alone people being worried about being perceived as a liar or evasive about the truth. Engaging more with these peers about your genuine feelings about Bob really risks adding a lot more drama to the situation if they ever fear it’ll harm their work-life more to be discrete about the OP’s feelings vs sharing with Bob.

          It’s not so much about these peers being good/bad people – it’s just that their livelihoods include 40+ hours a week dealing with a Bob reality.

          1. Alanna*

            Given that OP and Bob worked closely together, I think it’s pretty normal for people to occasionally ask if they’ve kept in touch or to mention if they’ve seen OP — it’s just normal human curiosity to want to know how people are doing in their new role, and someone they worked with closely for years might be someone who would know. It doesn’t have to be some kind of three-dimensional office politics checkers.

        2. LG*

          I totally agree with this. The mental energy that the LW is expending on this issue is ridiculous THREE YEARS after leaving that job. There is no way to satisfy the irrational expectations of former boss, and any attempt made will make him feel justified in his immature behaviour. Keep on ignoring him.

      4. MigraineMonth*

        “Wow, that’s pretty weird” is exactly what I would think if Bob complained to me that someone he *used to manage three years ago* is ignoring him. I don’t care how small the industry is, that’s bizarre behavior.

      5. SeaCow*

        I like these responses as there is NOTHING to apologize for. You don’t owe an apology to Bob nor colleagues for Bob’s issues.

    3. Artemesia*

      Addison’s advice seems spot on to me. You could respond blandly to one of his messages and the let a few months go by for the next one. At a conference you look at him as if you think you remember him, oh yes BOB, good to see you. Bland. Give him nothing to engage you with. If he whines about your ignoring him it is ‘oh I’ve just been so crazy busy with the new job, how are you doing?’ and then go get a drink and avoid him.

  2. Daniel*

    Any chance that it would be worthwhile to tell Bob that you’ve mentally moved on from your old your old job? I don’t see #2 being fair to yourself, and #3 seems like it would cause more drama. And if Bob is still going on about you three years after you’ve let, I’m not sure if simply ignoring him would work.

    1. Radioactive Cyborg Llama*

      And to follow on to that, I wouldn’t want for LW to sound like it’s taking years to get her feet on the ground in her position. I’d advise the LW to even stop thinking of it as her “new” job!

  3. Clefairy*

    I had to literally break up with an old boss who wouldn’t leave me alone, and I got to the point where I just didn’t care what she was telling other people anymore, it was worth it to not have to constantly feel pressured to respond to her. I figure, her issues as a manager (and a human) were pretty apparent, so reasonable people wouldn’t give much stock to what she was saying about me for not talking to her. And if someone DID take stock, they clearly didn’t know her and/or me very well, or they are unreasonable themselves, so whatever.

      1. I went to school with only 1 Jennifer*

        A friend break-up kind of thing, maybe? “This isn’t working for me. Please don’t contact me again; I hope your life goes well.”

      2. Clefairy*

        I told her that I needed to prioritize my mental health, and to do so, I needed to distance myself from her, but that I wished her all the best.

        1. Rainbow*

          Ooh. I might use this. I keep seeing my old boss at conferences (small-world industry), and she keeps being like, “omg let’s catch up!”. And I don’t know how much more suddenly realizing I have something urgent to do I can acceptably get away with. Suspect she only wants to catch up to try and find out what my current company is up to, given that the last time we socially hung out it was actually a ploy to get info that led to her getting the position of being my manager.

          1. Clefairy*

            Just be prepared that she’s probably going to be offended, you have to just not care haha. I blocked my boss’ number after the breakup and just put her out of my mind afterwards, it’s been great lol

    1. singularity*

      This is what I was going to say. If LW’s industry is that small, then people already know her former boss and his reputation. It speaks for itself. Probably no one will ask intrusive questions because they’ll already know, and if they do, use one of the generic answers Alison provided and change the subject.

    2. singularity*

      If LW’s industry is that small, her old boss’ reputation is likely known at both conferences and among other people. She doesn’t need to respond beyond surface level pleasantries because people will know why she distanced herself.

      1. Eldritch Office Worker*

        I don’t know if that’s true.

        “I have explained the full situation to my boss and he seems understanding, if a bit confused by how firm my decision has been to cut off a former boss in a small industry like ours.”

        It sounds like this is far enough outside the norm that it might reflect poorly on OP regardless of Bob’s reputation. OP seems pretty confident in their own reputation, so maybe they don’t care, but I don’t think it’s fair to assert there won’t be consequences because we think there wouldn’t be in a reasonable world.

        1. Observer*

          Yes and no.

          I think that the problem here is that the OPis refusing to even do the surface level thing or making the assumption that it’s all or nothing. Either they totally cut off Bob or they be truly responsive to him.

          I’d be willing to bet that if OP were willing to do the “surface pleasantries” thing and Bob STILL complained, that would have people wondering what’s up with Bob.

          1. Jellyfish Catcher*

            I agree. You need to conduct “surface pleasantries” with other companies in your industry for your sake, your company’s sake and because it’s part of your job.
            Refocus this as being at your best and not about Bob.

            You set aside your emotions and past with Bob and substitute your professional skill. It’s a small industry and you don’t want to cause any perceived weirdness.
            From now on, The Bob Issue (TBI) is dealt with via your professional management skills, just like any other minor, recurring, distasteful part of your job, that you cannot change.
            You are pleasantly bland, courteous, and chat for X minutes at a conference.
            If it helps, think of Bob as a sad, oozy, ugly alien dragging through the
            conference hall when you see him, and have pity for him.

            Aside: gonna steal the phrase “surface pleasantries.”

        2. ecnaseener*

          Yeah, we can talk all we want about how Bob’s reputation should precede him enough that everyone gets why LW doesn’t want to talk to him, but according to the letter, that’s not the case.

          It sounds like Bob’s main problem was inaction, so he might have a reputation for being mediocre but not necessarily an “oh yes of course his former employees want nothing to do with him” reputation.

          1. Rainbow*

            Yeah, I definitely know of people who have a better reputation on the conference circuit than they do among people who have actually worked with them.

            1. Journey of man*

              Ooh I like your observation and phrase better reputation on the conference circuit” than at work.

              1. Splendid Colors*

                Doubly so in academia.

                Lots of “famous Principal Investigators” turn out to be glassbowls propped up by their post-docs and PhD students.

            2. metadata minion*

              I’m also thinking of a former boss of mine who is a genuinely lovely and gregarious person who I would probably have gotten along with great as a coworker, but who in a lot of ways was a terrible manager. When people asked about him at conferences, I had to quash my “ugh, @#%ing BOB” reaction, because everyone was always delighted to hear I knew him because wasn’t he just the best?

      2. Butterfly Counter*

        With people like Bob, their reputations don’t really get more detailed than “He tries to be liked,” and for a lot of people, that will make him likeable. So to have someone reasonable who wants nothing to do with “Likeable Bob,” it confuses people.

      3. The Pragmatist*

        OP, You know, having a very occasional drink with your former boss at a conference does not mean you endorse everything he has ever done or said. And it will help you politically in your industry to stay in touch very occasionally. That is what you should do.

        Networking is not only for people you adore.

        1. Alanna*

          Yeah, the idea that you need to be formally breaking up with old colleagues you don’t particularly care for seems misplaced to me. It feels like it was imported from other contexts (family, romantic relationships, maybe friendships) where there’s an expectation of continued closeness, and is part of a cultural trend more broadly toward explicitly Cutting Toxic People Out Of Your Life. Whether that trend is good or not is a separate issue, but it really doesn’t seem to be something necessary here.

          Making a big deal about how you’re going no-contact with your old boss (to him or anyone else) is a pretty dramatic thing to do, and it’s going to make people think that OP is the drama, because… well, it’s a pretty dramatic thing to do.

          1. Clefairy*

            The thing is, some old bosses try to force closeness. They don’t understand that once the working relationship is severed, the relationship should change and fade into the background. I don’t think it’s fair to assume that OP is being dramatic- if they feel the need to cut out this old boss, I think it’s worth giving the benefit of the doubt that their boss is acting inappropriately/more intensely than is the norm.

            As mentioned above, I’ve officially “broken up” with a former boss- and it wasn’t me being dramatic, it was because they were extremely toxic and kept trying to force themselves into my life, both personally and professionally, when they had no right to do so. The straw that broke the camel’s back (after many other things, some of which were much more toxic than this) was a really snippy text from her saying that it was clear I hated her because I wasn’t responding to her text messages quickly, but even though I hated her, she would always want what was best for the people under her who she molded into what they are today [she…definitely did not mold me into anything], and so I should check out a job posting that was in a completely different industry, and extremely junior compared to where I was in my career. It was inappropriate, weird, and condescending, and so I cut contact with her. That’s not dramatic, that’s setting strong boundaries when more subtle boundaries have been stomped over.

          2. I have RBF*

            Bob is making the drama in trying to act like he has a right to continued contact with a former employee. That’s on Bob.

            Some folks like a clean break from former jobs and coworkers except for a few deliberately chosen people. It lets them focus on their newer position.

            What Bob is doing, especially pushing the issue with other former coworkers, would start to feel like stalking after a while, especially with Bob moaning about them not responding to texts several years after the employment relationship has ended!

            I would be flat out floored if some of my former managers or coworkers started texting me and expected me to respond, even the ones I still like. If I saw them at a conference I would be cordial, maybe catch up with a basic level “what are you working on now”, but not a long, detail heart to heart. They are people I work with, not close friends.

    3. Squeakrad*

      I’ve worked in a lot of really niche small industries and have many friends who have, in small towns, big cities, you name it – and I don’t know if any industry so small in any particular location that ignoring one person would cause any kind of repercussions. From the OP’s original responses that they considered, I think this is a case where they are overly concerned with what other people are saying, and with being nice to Bob, neither of which I would worry that it would affect their current position.

      1. Alanna*

        Yeah, I think drawing a hard boundary, as others are suggesting in this thread, could have repercussions — that’s just something that’s really not done often in professional settings absent something really awful (harassment, abuse, etc), and could make OP sound like a little bit of a drama llama.

        But ignoring invitations to keep in touch? I’m in one of the gossipiest industries there is (media — we gossip for a living!) and “oh, Old Boss tried to stay in touch with me but I wasn’t really feeling it” or “I’ve reached out to her a few times, but nothing” is a boring, normal tale as old as time. It’s not unusual to ask if people are in touch with former colleagues, and it’s also not unusual at all for no to be the answer.

    4. tamarack etc.*

      Yeah, I’d probably tempted to write something that is a) short (important!), b) super polite/friendly in tone, c) not apologetic (!!), d) makes it clear that I’m not interested in contact.

      “Hey Old Boss, [old contacts] mentioned you mentioning me / sending me messages. I guess they slid off the top of my inbox as I’ve been so busy at [new role] lately. The time at [old job] was sure instructive, wasn’t it? I’m enjoying myself a lot at [new role] these days and am happy about all the new directions I’ve taken on. Hope all is good with you. I’m sure we’ll run into each other in the near future at [events].”

      And then if you run into him at an event, have a 10 min chat over a beverage. Done. (Rebuff everything beyond that with an “oh, that won’t fit my schedule right now, sorry!” excuse. Other people in the industry will understand why you keep your distance. Plausible deniability is the word.)

  4. Bluebonnet*

    I wish certain people from the past would stay in the past where they belong. I am glad you are in a much better job situation, OP!

    1. The Pragmatist*

      I think there is much to be said for keeping your friends close, and your enemies closer.

      OP should have the very occasional coffee or drink with her former boss. Ghosting him will not help her reputation.

      1. Meep*

        Maybe I am just young, but I support respecting people’s boundaries and after three years Bob should’ve 1-800-GET-A-CLUE.

      2. Tomato Soup*

        Considering the fact that he’s being honest about why he’s sad, repeating this story only hurts his reputation.

  5. Pool Noodle Barnacle Pen0s*

    I would confront Bob and ask him why he feels the need to discuss me and personal matters involving me to mutual acquaintances and peers. Because yes, BOB, that does make me feel rather upset with you. If he can’t act like a grownup, the least he can do is explain his reasoning for this behavior.

    1. The Pragmatist*

      “She used to work for me and now avoids me at industry conferences” is not a “personal matter”.

    2. Mf*

      I think there’s merit to this approach if you soften it a bit. “Hey, Bob, I’m hearing from former colleagues that you think I’m avoiding you. I actually wasn’t but if you continue to say stuff like that, I may have to start!”

  6. Not Sorry*

    I agree with this advice. I had something similar happen with a former coworker, who really wanted to be my friend, but was the kind of person I didn’t trust or enjoy spending time with. I tried outright ignoring her calls and texts and eventually she was reaching out to other people we both knew in the industry to ask if I’d changed my number or if they knew why I was ignoring her.

    I did pretty much exactly what Alison recommends. I responded sometimes, and was always apologetic but “so busy right now!” I think she eventually just gave up. Haven’t heard from her in a couple years and it won’t be weird if we run into each other because now it genuinely seems like we lost touch. Oh darn!!

    1. ferrina*

      This is what I’ve done with toxic family members. “Oh, so sorry I missed your message! Things have just been crazy lately! Once things settle down, let’s catch up!”
      And then never reach out. Because “Gosh, this thing just came up….”

  7. Sloanicota*

    Part of Bob’s issue is no doubt that he planned to network with OP and her new contacts, which is why he can’t just let it go. In a small industry, unfortunately, if someone is determined to network with you there’s not a lot of ways to avoid them forever. Personally I would be cordial but chilly and not encouraging of any greater intimacies; definitely don’t respond to texts as it just confirms the number is right and that you see messages there, giving him immediate access.

    1. Don’t put metal in the science oven*

      This is a good take. He might be desperate to be networking with everyone he can in a small industry. Cordial distance might be the best political move.

    2. JTB*

      It would fit his people pleaser and conflict avoidance personality. Ironically him thinking it’s a problem with him would be an accurate read, just not for the reasons he thinks.

  8. Keymaster of Gozer*

    If you block him (recommended) and he mouths off about that then remember he has a limited audience for that kind of behaviour. People will get bored after a week or so of ‘so and so won’t reply to my texts!’.

    1. goddessoftransitory*

      Eventually they are going to at least think “are you in third grade, Bob? TAKE THE HINT.”

    2. Jenny*

      I’d grey rock Bob as much as possible. Any direction confrontation and I think he’ll whine to everyone he can about LW.

    3. I have RBF*

      “I’m sorry, I don’t respond to texts that are not from my immediate family, friends or current coworkers about business. If I did I would be on my phone all day. Hope you are doing well, and it’s been great to catch up with you. Bye.”

  9. Filthy Vulgar Mercenary*

    I actually don’t fully agree with this. I would tell Bob unless I was worried about some kind of impact to me. I wouldn’t hold any expectations that it does anything, and then I would add the breezy ‘super busy see ya!’ comments when I saw him, but he is directly asking. If he doesn’t change it wouldn’t be for lack of me telling him. Maybe no one ever has said ‘whatever mental gymnastics and concessions he’s made in his head are actually not having the impact that he thinks they’re having’ (ie like a trade off that some sexism is okay if a person has a kid) and not ever stepped back to question it.

    Maybe not, and I would say it and then let go of any attachment to it at all, but I would not be unable to say it.

    1. Unkempt Flatware*

      I’m actually this type as well. I want to and feel a need to tell bosses how badly they made me feel. I’ve done it with almost every boss I’ve ever had. However, I’ve come to the realization that it doesn’t make me feel better. I honestly don’t know what would besides more therapy and life experience.

      1. Qwerty*

        Captain Awkward has a good post on this from 3/25/2020 (I happened to be browsing the archives today). The recommendation was write a letter getting your feelings out and saying all the things you need to say. Burn the letter, do NOT send. Then write out the response that you would want/need to hear.

    2. FD*

      I kind of lean this way too, *if* the LW is in a position where they can afford to burn that bridge. It’s true that he probably isn’t going to change, but so often people continue both with offensive behavior and with enabling offensive behavior because no one has ever called them on it. This is particularly powerful if the LW is someone Bob would respect, e.g. men often take it more seriously if a man calls them out for sexist behavior vs women.

      If doing this, I think I would focus on something like, “Hey, I’ve heard that you wonder why I haven’t been more proactive about keeping in touch. There were some things that happened when I worked there that made me really uncomfortable. In particular, the way that [person who did bad thing A] was allowed to continue [doing bad thing A], and [example 2] really left a bad taste in my mouth.”

      The crappy thing is though the LW has to be ready to know that bridge is now burned, and Bob may say mean things about them. Three years later, with their reputation at a new firm, this might or might not be something the LW can afford to do though.

    3. ferrina*

      I would say it and then let go of any attachment to it at all

      If you want to say something for you, this is the right way to do it. I wouldn’t expect Bob to change. The Bobs I’ve run across aren’t lacking information, they just don’t want to change. And you can’t make someone change who doesn’t want to change (though they may claim that they are trying, feed you a sob story about how it’s not their fault that they are this way, then accuse you of not being patient or understanding. They casually ignore all the damage that they’ve left in their wake, which often disproportionately falls on women and POC).

      1. Hannah Lee*

        As OG Miss Manners once advised – people who are misbehaving in some way that is super obvious – for example: repeatedly hounding someone who is not reciprocating an interest in contact, ignoring problem employees so that other people are subjected to jerks on a daily basis, etc – that’s an indication that whatever they’ve got going on, whatever need they are filling with the misbehavior is WAY more important to them then your comfort or convenience, your opinion of them, or standards of behavior (professionalism, etiquette, etc) You pointing out the ways you’ve seen them misbehave isn’t going to change them one bit, they’ll just keep rolling the way they’ve always rolled.
        The example she was talking about was someone who repeatedly showed up at a family member’s home to visit without calling first, but it really is true of so many situations.

        The only thing you can do is set boundaries around YOUR behavior. Decide what level of interaction you want to have with Bob (weighing your own preferences for zero weighed against whatever minimum is required to not drag you into drama at conferences, etc) and stick to it no matter how many Bob handstands he does. Never ever respond to his most annoying behaviors. If you do occasionally respond, choose to respond only to his most “normal” or “professional” of contacts.

        Also, don’t* feed any flying monkeys that come shrieking your way … to them, respond neutrally or with a confused look that indicates you have no idea what they are talking about RE Bob. “him? I worked with him years ago… no there’s no issue I’m aware of”

        * and by don’t, I mean don’t ever with work, industry people. Even if it’s someone you think knows the deal, even if it’s after dinner and drinks at a conference when everyone is letting their hair down. IME with the Bobs of the world who someone manage to stay employed and maintain at least a neutral reputation (how? who knows) even a *whisper* of ‘yeah, can you believe that guy?’ in response to someone *else’s* big giant Bob’s a dope story, will somehow ricochet back at you and morph into rumors of there being Drama, bringing Bob and his nonsense front and center in your work life. Which should be the last thing you want.

  10. Hiring Mgr*

    Has this been going on for three years, or did Bob just recently start getting in touch again?

    Bob sounds like an inept manager for sure, but it doesn’t sound like there’s any harm in a mild
    “good to hear from you – hope all is well” reply.

    1. Antilles*

      This is what I want to know too.
      In either case, it’s ridiculous, but if he’s been like this for three years, my impression is much different than if he recently remembered you exist and this has all of a sudden started.

    2. Sick of Workplace Bullshit (she/her)*

      The OP doesn’t want to keep in contact. I don’t see why Bob’s feelings should trump hers.

      1. Buffy Rosenberg*

        I would also give those type of replies occasionally. It’s not so much about Bob’s feelings for me, but rather the fact that he’s a former boss, it’s a small industry, there’s gossip and drama potential, and there’s rarely any benefit in making an enemy out of anyone unless it is absolutely essential.

        Very little work would go into it. LW could even just say things like “Hi Bob, hope you’re well, can’t chat right now but have a great weekend” or whatever once in a while.

  11. Pierrot*

    I don’t have any advice, but I went through something similar with a boss in my first job out of college. It was at a nonprofit with a specific focus, so that area of nonprofits was a small world. I met him at a conference and he helped me get the job at a highly dysfunctional organization. He didn’t run it, but he was a pretty senior manager.

    Anyways, he did a number of similar things as Bob while also being the person making overtly sexual comments. It was the form of sexual harassment where the person isn’t specifically directing the comments at employees, but he made a lot of inappropriate comments that made people uncomfortable. He was not a good manager in most ways and had 0 integrity. I left the organization and made up a reason why I was leaving in the hopes that I could put it behind me. I blocked him on Facebook and I think he assumed that I deleted my account. He kept following me from different accounts on Instagram and Facebook, then he started texted me about job opportunities. I just never responded. It sucks because I can’t use him as a reference, but I’ve worked around it and he wouldn’t be the best reference regardless.

    He’s one of those people who had a good reputation in our field from afar, but people who actually worked with him knew what he was really like. I suspect that Bob is similar, and people who know him probably understand why LW would distance herself. I think that if you’re really concerned, you can occasionally respond in the most boring way possible to stave off in depth conversation.

  12. Clobberin' Time*

    Don’t talk to Bob. Don’t reach out to Bob. If you respond, you will have taught him that his tactics work in getting your attention, and it will be harder to get him to go away next time.

    Colleagues who are passing on Bob’s sad messages are probably hoping there is some interesting gossip. Don’t take the bait. If they talk about Bob, give a non-responsive listening noise and firmly change the subject. “Huh. Anyway, do you know what conference room the Advanced Llama Grooming seminar is in?” (And if they persist, it’s OK to say “That was a subject change; I don’t want to talk about Bob’s feelings.)

    If you run into Bob at a conference, don’t engage. There is no law saying that you must answer his questions or soothe his feelings. Say hi, be civil, and if he starts blabbing about how sad he is and why are you mean to him, break off with a non-sequitur like “Well, it’s great seeing you! I hope you enjoy the conference” and then briskly walk away.

    Never underestimate the value of refusing to follow social scripts inappropriate people demand you follow.

      1. Clobberin' Time*

        Isn’t it interesting how that never seems to run both ways? Why isn’t Bob worrying that his misbehavior is going to cause him problems in their very small industry?

        1. Buffy Rosenberg*

          Well, maybe Bob is worried about that and that’s why he’s getting anxious and pushy about his relationship with the LW… it’s just that he lacks the awareness of where he’s going wrong, or the relationship management skills to address it properly.

  13. Goldenrod*

    Yep! I agree fully with you, Not Sorry, and also with Alison: “cheerful, vague, and brief” is the guideline to follow here.

    Like Alison said, Bob won’t change because of a critical email – even if everything you say in the email is true, people hate criticism and he won’t take anything away from it other than “you’re mad at him” or “you hate him” – which is bound to generate more drama and encourage further interaction.

    On the other hand, if you just keep it light and breezy – and keep being too “busy” – you will be providing absolutely nothing to feed the drama, and Bob will eventually get bored and move on to all the other people he needs to get approval from…..

    Good luck!!

    1. Observer*

      And even if *Bob* doesn’t get bored other people will. Because how many times can you repeat a variation of “OP won’t spend time with me” without any more material.

  14. Jenny*

    I hope it heartens LW that if a was one of her colleagues CCed on one of Bob’s “I’m sad” emails, I’d think Bob is being really creepy and inappropriate. That reflects really badly on Bob, not on LW. I sincerely hope that’s how other people would react

    1. Jenny*

      Just adding I realize I read OP as female with no actual textual support but my reaction would change not at all based on gender. Bob is creepy.

      1. Eldritch Office Worker*

        “But he wouldn’t relinquish any power to me, instead always asking for my advice and never taking it.”

        This is such a common female experience. If OP is male, it still sucks and doesn’t change the advice. But speaking as a woman, this whole dynamic is hellishly familiar.

      2. Letter-Writer-Bob-Trouble*

        Letter writer/OP here! A lot of people in the comments have assumed I am female, and for starters, I am. Furthermore, it’s fascinating to me that so many people assumed that (and correctly!). I have a feeling this is a pretty common experience for women with male managers who promote them, don’t take their advice, and just generally do all the things Bob did.

        1. Rainy*

          Having a female 2nc gives dudes like that a certain amount of plausible deniability for the rest of their nonsense, so I think it happens pretty often in this kind of situation. I wouldn’t be surprised at all if he gets a lot worse the farther down the food chain someone is.

          1. goddessoftransitory*

            Yeah, it’s a pretty common camouflage of “he can’t be a misogynist, he’s got a female XO!” while the real story is that the guy’s got about as much respect for her as Jabba the Hutt did for Leia.

        2. Qwerty*

          Honestly if I heard that Bob was “feeling sad” because his female former employee was “ignoring” him…I’d assume that there was harassment or some form of creepy factor going on.

          But then again, I’m a woman and that’s why I avoid multiple of my former managers. The dudes in my industry wouldn’t jump to that conclusion.

        3. Anne Wentworth*

          There’s just something about a man claiming to be “sad” that a former colleague won’t respond to his persistent messages/give him the attention he wants that screams “tone-deaf man harassing a woman.” A man like Bob would likely feel uncomfortable saying he was “sad” because another man ignored him; he might feel it but he wouldn’t broadcast it to the world.

        4. Heidi*

          We’ve been told in past posts that most letter writers are female, so the assumption might not be based entirely on the content of the letter.

          1. Meep*

            That makes a lot of sense. Most of the commenters appear female too. I know there is some bias that you are going to see your own gender on the screen. But women often have to deal with the bulk of the emotional labor in and out of work. It makes sense why we would ask for help more. (In addition to being more willing/’trained’ to ask for help compared to our male counterparts who often view it as a weakness.)

        5. Meep*

          Yeah… And also being female unfortunately means we are prone to feeling like we need to tend to the Bobs of the world (aka big babies) and their feelings. Don’t second guess yourself! You don’t owe this guy anything.

        6. Mf*

          For me, what gave it away is that Bob is acting like he’s entitled to your time and attention. In my experience, men are way more likely to treat women like that than other men.

  15. KTC*

    I’m a fan of being direct. If people ask if you’re ignoring him, I would respond with “Yes! I am ignoring him. Not a fan of his behavior/style at my last job and I don’t wish to be associated with him at all.” You don’t have to go into detail, you don’t have to trash him, BUT you are sending some signals that should this person should tread carefully. Given his abhorrent behavior I’d be more worried about people thinking I purposefully kept in touch with him than people knowing I chose not to. As far as communicating with him directly, I’d block his number and not give it another thought. You don’t owe him a thing. #ghostthatjerk

    1. Observer*

      If people ask if you’re ignoring him, I would respond with “Yes! I am ignoring him. Not a fan of his behavior/style at my last job and I don’t wish to be associated with him at all.” You don’t have to go into detail, you don’t have to trash him,

      Except that this *is* effectively trashing him. Yes, it’s deserved, but it invites further questions, gossip and potential drama. That’s not really what the OP needs – she needs to starve this whole thing of as much oxygen as she can.

    2. Silence*

      That is trashing him. I’d recommend something like ‘yeah we don’t keep in touch. He forgets I don’t work for him anymore ‘ followed by a subject change.

  16. Someone Else's Boss*

    I cannot imagine being that salty over a previous employee ignoring me. I don’t expect any of them to want to stay in touch – work is a means to an end, and that end is not friendship with your previous boss.

    1. goddessoftransitory*

      The only circumstance I can come up with is if I was actually married to said employee and they haven’t signed the divorce papers!

  17. zuzu*

    I think there’s value in responding once, and once only, and addressing the contacts he’s made. But in a “By the way, it’s the oddest thing — I’ve been hearing from my boss and my colleagues that you’ve been contacting them to complain that I haven’t been responding to your messages. But they must be mistaken, because I’m sure you wouldn’t do something like that because you understand how busy we are in this line of work” kind of way.

    *Of course* you wouldn’t badger my coworkers, Bob! Perish the thought!

    The key is to make sure you don’t give any conversational openings in your response. Not even a “How are you?” or “Hope you’re well.” Just, “I’ve barely had a chance to breathe lately, but just wanted to drop you a note to acknowledge your email and to say I’m completely swamped, but I hope to see you at conference.” And then the Columbo by-the-way.

  18. Sara without an H*

    First, LW, please dismiss from your mind any idea that there’s anything you could put in an email that would make Bob get a clue. It just doesn’t work that way, and he’d probably wind up telling everybody he knows that you sent him an abusive email After All He’d Done For You.

    Instead, I’d go with Alison’s “minimum contact” recommendation. I saw this described as a “Hallmark relationship” somewhere else on the internet, i.e., you do the minimum to maintain the relationship without any kind of intimacy. Think of sending holiday/birthday cards to a relative you’re not close to. Respond to his emails only at long intervals and then give the minimum of information. Eventually, he’ll shift his attention to something/somebody else.

    1. Lizzo*

      Yep, all of this. Any additional investment in this, either via communication with Bob or expounding upon the situation with your colleagues is just going to create drama even if that’s not your intent! You want to invest less energy, not more.

  19. scurvycapn*

    I’d continue ignoring Bob. If it comes up from coworkers again, throw him under the effing bus. “Yes, I am indeed ignoring Bob. When serious issues arose at [previous employer] including sexism and racism, he refused to act. He was more concerned with not upsetting people making disgusting comments than he was helping those hurt by them.”

    Hopefully that stops the questions. If you run into Bob, just tell him you’ve moved on. If he pushes, lay it all out for him as well. Unless your worry more about the politics than calling out degrading behavior, I guess.

    1. Jojo*

      The problem with throwing him under the bus is that it just increases the drama, and emotionally needy men who expect women to do emotional labor for them may view the drama as the LW’s fault, and not Bob’s fault.

      Limit engagement as much as possible, and then don’t give Bob any of the ego boost that he wants from you.

      1. Jam on Toast*

        I don’t think a statement that’s delivered calmly but factually about Bob’s shortcomings is going to feed the drama. Sure if LW ranted or used an angry tone, then yes, it would. But a level “Bob was an effective Llama programmer. But when I worked with him as my manager, I came to disagree with his approach to several important issues, especially when it came to protecting team members from harassment. While I understand that Bob feels differently about our time at Acme, I don’t think our management approaches align and I’d prefer to focus on growing in my current role.”

    2. AllTheBirds*

      This is important. Because the various contacts are thinking, “Why wouldn’t LW stay in contact w/Bob? He’s such a Nice Guy!” But he isn’t. Because he hides from his responsibilities and allows people to be harmed. A factual,”Bob allowed harassment when I worked for him and that’s a line I draw.”

      If we don’t call out the behavior…

  20. Samwise*

    I wish it were possible to say:
    Bob, yes I’m upset with you. You thought it was ok for employees to be sexually harassed, you refused to shut down racist jokes [add any other egregious actions or inactions that affected others — leave out the poor management you dealt with — stick with values and ethics issues]. So I hope you’re well, but I am not interested in getting coffee or going to lunch.

    Then walk away.

    It may be very hard to do this OP. Bob is a missing stair — if you can, don’t just jump over it with vague niceties.

    Been there. It is really really hard to do when you feel it may threaten your job. My own experience is, fortunately, it did not harm my job. I felt so much better about myself and it has made me braver ever since.

  21. LaLa*

    If it’s a small industry, and Bob has a reputation at work for siding with racists and misogynists, why would you be concerned about people wondering why you’ve fallen out of touch with him? If anything, I’d want other people to know that yes, indeed I AM ignoring Bob and distancing myself from him.

    1. Kevin Sours*

      Does Bob have a reputation for siding with racists and misogynists? I mean he does but does he have a reputation for it? And does that reputation extend outside of his workplace. A lot of people who focused on being liked succeed at that and reputations don’t always reflect reality.

  22. Momma Bear*

    What about “Huh, that’s strange that he would reach out to you like that. We don’t keep in touch. So what about the latest in llama grooming?”

    Whether or not your boss thinks it’s odd, he’s not the one being contacted by someone he doesn’t wish to hear from. They don’t need to understand it to respect it. I had a former coworker who crossed the line and after he said something horribly racist, I sent him a final email saying that I no longer wanted to hear from him, marked his address as spam, and haven’t looked at his messages since.

    1. Observer*

      What about “Huh, that’s strange that he would reach out to you like that. We don’t keep in touch. So what about the latest in llama grooming?”

      Sounds like a plan.

  23. Caramel & Cheddar*

    I want LW’s boss and coworkers to also push back on Bob, or at the very least stop telling LW that Bob is asking about her. Unless he’s saying stuff that might affect LW’s reputation, I wouldn’t want to hear about it. And if it *is* affecting her reputation and her colleagues know Bob is in the wrong, they can say “Wow, that’s not our experience of LW!” and change the subject.

    If LW is ignoring Bob’s various overtures, then there’s no reason she needs to know about what he’s saying if people stop deliberately participating in Bob’s antics like this.

    1. Rainy*

      Unfortunately, for people who like drama, you have to be explicit about that. Professionally I would be a little more diplomatic and say something like “It’s weird of Bob to say something like that about me! I really prefer not to engage with that kind of talk, especially in my professional life, so I’d appreciate it if you didn’t tell me what Bob was saying about me! Thank you!”

      When my sister kept telling me what my MIL was saying about me on Facebook, I was a lot blunter: “I don’t care what she says and I’m happier when I don’t know, so don’t tell me. Thank you!”

      1. JTB*

        Drama llamas fixate on lack of information and start to speculate. OP is caught in a no-win situation, say nothing and people start reading their own ideas into it or divulge the truth to some degree and people talk anyway at least until the next turn of the gossip mill introduces something new.

  24. goddessoftransitory*

    Bob’s need to be liked is what’s powering this, but I think in a specific way.

    He is not unaware. In fact, he’s quite fully aware of why you left, and he is desperate for you to change your mind, reassure him that not disciplining someone who would make jokes about child porn* (OMG) is A-Okay, basically be his emotional support animal to change reality to the version where he’s Great Bob and hasn’t lost a ton of good and now angry employees who may be giving pointed answers to people in your industry as to why they left, and his bosses may finally be noticing.

    If he can get you to somehow retroactively stamp his behaviors as Just Fine, he doesn’t have to do any self-examination about how his terror of actually doing the difficult parts of his job are getting him the opposite of what he wants. He can enjoy his version of being jolly Bob, if you’d just not make him sad!

    Don’t fall for it. My mantra is “Kind, Polite, Professional, Done” for this kind of thing. If you run into him the brief “so busy good to see you byyyyyye!” brush off. If others in the industry ask about Bob’s tales of woe, just shrug and say “We’re both busy, oh well!”

    It’s been THREE YEARS. Even if there was anything you could have done to “fix” this situation, that window is closed. If Bob wants to keep pounding on the glass that’s his look out.

    *And frankly his excuse of that guy’s wife having just had a baby??? My reaction would probably be You’re right, let’s call the cops instead. My God.

    1. Lily*

      “And frankly his excuse of that guy’s wife having just had a baby??? My reaction would probably be You’re right, let’s call the cops instead. My God.”

      Yeah, that bit really icked me out.

    2. Observer*

      not disciplining someone who would make jokes about child porn* (OMG) ~~~ SNIP~~~ And frankly his excuse of that guy’s wife having just had a baby??? My reaction would probably be You’re right, let’s call the cops instead. My God.

      So much this!

      And I agree with the rest of your comment.

    3. Momma Bear*

      Agreed. I think it bugs the snot out of Bob that OP ignores him.

      And if it’s “odd” that OP is ignoring him and people know OP to be a stand up person, then maybe they’re wondering what Bob did to warrant being ignored. That’s what I would be thinking – ‘I’ve known OP to have good judgement so what’s going on here? And why does Bob care 3 years post exit?”

      OP’s approval/opinion of Bob matters to Bob more than Bob’s approval matters to OP.

    4. Adrian*

      In a way, Bob actually could have been considerate of the wife.

      I learned only long after I’d left, that my colleague Scott had been despised by lots of people he dealt with in his job. I don’t think it was sexism, racism or anything of that sort.

      The boss didn’t fire him because after years of trying, Scott and his wife had finally had a child. It had been a super-difficult pregnancy, which they nearly lost at least once. Mrs. Scott was a very nice person, and for her sake the boss didn’t want to put her husband out of a job at a time like that.

      1. Buffy Rosenberg*

        Adrian, why would that boss prioritise Scott’s wife over his own employees, though? If Scott was impacting them and the only reason he wasn’t let go was his wife, and their family, that is a shockingly poor priority

        Maybe some of Scott’s also had comparable things happening in their lives which Scott’s behaviours worsened?

      2. Observer*

        There is a HUGE difference between a competent jerk who you can work with, kinda and someone who apparently endorses child porn!*

        And if someone has a kid they NEED to know that their spouse is ok with it! Even if it took years etc.

    5. laser99*

      You are correct, but the problem isn’t going away. If the LW is willing to send an email outlining the following—“You seem to be laboring under the assumption that we are friends. We are not friends, and never were. The reason I left your employment is your inexcusable behavior regarding [insert specific examples here].” I’m guessing this would make old Bob so uncomfortable he’d finally give up.

  25. I don't mean to be rude, I'm just good at it*

    I’m so sorry. I didn’t realize your emails were going to my spam folder. I’ll try to fix that.

    1. The Gollux, Not a Mere Device*

      She can “fix that” where “that” is “didn’t realize” and then go home and set things up so she absolutely realizes that his email is going to the spam folder because she just started sending it there.

  26. Falling Diphthong*

    OP, you know the saying “Email like it’s being read aloud at a deposition?” For that last option, picture Bob going around the next conference, or going to some sort of discussion thread for your field, and asking what people think of this email he received from you laying out his personal failings.

    Bearing in mind these people likely know him as a pleasant guy who wants to be liked, not as a bad manager. That’s going to read like you are a large part of the drama. You want to grey rock his outreach, gosh been busy, new job is taking all my time, etc. Not suggest that you sit at home fuming about Bob and thinking up real zingers that would show him–zingers almost never do.

  27. Captain dddd-cccc-ddWdd*

    Continue to ignore. Coworkers etc won’t think badly of you for ignoring him, as they also know what he’s like. I bet they’ve told you he’s “sad” etc just in a FYI, he’s saying this sort of way. I would be very surprised if they judge you.

    I almost wondered if he’s looking for a way in to OPs current company…

  28. Observer*

    I would probably just occasionally send a low effort response to him on delay with no information except for how busy you are. Or maybe something like Allison suggested along the lines of “I’ve just been so busy. And I’m really in such a different space now and that’s why I often don’t respond.”

    More importantly, I think you need to take a step back. Bob is a bad boss. It also sounds like he’s also something of an idiot who failed upwards. None of what he did was good, but it wasn’t personal. It’s to your benefit to recognize that and treat the whole thing less personally.

    So, when people tell you that “Bob is sad” that you are ignoring him, don’t take it personally and don’t get worked up over it. Also, don’t do so much sharing. Just shrug and say that you’ve been really, really busy. “Say hi to him for me.”

    Your boss is “a bit confused by how firm my decision has been to cut off a former boss in a small industry like ours” because this seems to be a lot of emotional energy. I imagine he’s wondering why you are expending so much energy while potentially sparking gossip.

    There is no point in trying to explain anything to Bob. There is no upside – you’re not going to change his attitude or behavior. But there is a lot of potential downside. If he has a reasonable reputation (not stellar, just not “Everyone knows he’s a jerk” levels), and he starts talking about how you “lashed out” at him for “just trying to touch base”, that’s going to make you look like the one with issues.

    1. Tomato Soup*

      Based on the Bob-like people I’ve known, I don’t think any response would be a good one. The people I know would take literally anything as an invitation to keep messaging. They read it how they want.

  29. Fluffy Fish*

    Do not worry about what others think. If a guy at work or in my industry complained to me about how his former employee ignored him (weird enough) and he’s SAD (okay now its just very weird), I am so not thinking its a you problem.

    I’m thinking Bob is very weird and very needy. And I’m probably making a face that shows that.

    Ignore away. You’re fine.

  30. HonorBox*

    I think it is really odd that Bob is reaching out to people and they’re saying something to you. Perhaps just a quick reply to Bob to say that you’ve been incredibly busy and will see him at _____ (conference). Then ignore him. Say hello at the event at which you see him. But go ahead and ignore him. And if someone says something to you about Bob point out how weird it is that someone is doing what he’s doing.

  31. Kevin Sours*

    I would not address Bob directly at all. It might be worth, however, pushing back on colleagues who mention it. How much depends a lot on your industry and what the consequences are. In an ideal world you could be forthright about your experience — we’d all be better off if people could talk openly about bad behavior. But it’s not an ideal world and being seen as “starting drama” in a small industry can have repercussions.

    However honest but vague can be your friend: “I didn’t really enjoy my time at X so I really want to focus on things at Y”. And if you run into Bob just a chilly “I’m focused on my work at Y”. You don’t owe him an explanation and it won’t do any good anyway.

    But if that’s too risky, the “I’m busy, bye” approach is a valid fallback.

  32. Anonymouse*

    Response to the people telling you about Bob:

    Hasn’t Bob found anyone new at the old company to provide emotional support besides me? It’s been three years. I’m glad you are volunteering to help Bob through these times.

  33. Other Duties as Assigned*

    I really liked Alison’s take on managers refusing to tackle difficult workplace issues for fear they will be disliked: “it nearly always leads to the manager being disliked by their best employees.” It really captures a lot of my experiences with bad managers and I’d never heard it put exactly that way before.

  34. learnedthehardway*

    Ugh. Since it is such a small industry and your current manager doesn’t seem to get it, I would take that as a hint that Bob is not really totally escapable. Unfortunately. I think your strategy should be to think about future implications of cutting him off at the knees, and managing according to how much you may need him as a reference or for job leads in future. Yes, that’s mercenary. However, you do have to look after your own interests here. It’s pretty clear that Bob has contacts and influence in the industry, if people are reaching out to you to ask why you haven’t gotten back to him.

    That said, you can minimize contact over time and keep him at arm’s length. I would respond to one of his texts and say you’ve just been so snowed under that you haven’t had time to breathe and you expect this to continue for the next six months or so. Such a big transition, don’tcha know.

    Then, respond on a very delayed timetable to future texts (they’ll happen).

    Over time, he’ll get busy and will adjust to whoever his new direct report is, and you’ll fade from view.

    1. I have RBF*

      “I don’t respond to texts from former employers as it could be seen as a conflict of interest with my current job.”

      1. Buffy Rosenberg*

        But keeping in touch with former employers/bosses is SO common, this just feels like so obviously an excuse that it would almost be better calmly giving the real reason.

  35. JustMe*

    I know your industry is small, OP, but is there any chance you’re working for a competitor of your old company? Or, for example, did you move from a boutique agency to a much larger and more established company? If so, it’s possible that Bob is looking for information or insider intel, and you could brush off all contact other than the occasional, “Hey, hope all is well with you, I’ve been pretty busy but hope things are still going well at [Company]” and explain it away as your new company not wanting you to divulge trade secrets, or something to that effect.

  36. Gary Patterson’s Cat*

    Option #1 is best. Ignore him freely and frequently albeit in a polite way. If you run into him, be courteous and friendly, but not overly buddy-buddy.
    If he acts hurt, you can always say you’re very focused on your new job and have more or less put the previous job behind you and are focusing on the future, etc. (Or whatever future focused language works).

    Perhaps that is chickening out, but in this case of a small industry, you’re probably better off not.

  37. Delta Delta*

    I had a Bob! Let’s call her Jane. I left a job because Jane was terrible (the job also was terrible, but Jane was the terrible icing on the terrible cake. so much terrible). When I left she was all, ‘hey! let’s get a glass of wine/go to lunch/socialize/catch up” and I’d always sort of deflect. The good thing is that Jane would never really follow up (different than Bob, I suppose). I got very good at waving hello across the room, or just saying hi and excusing myself if I saw her. Or she’d ask to get together and I’d say, sure sometime soon, and then name a month just far enough away that she’d forget. I have been ducking her for 6 years this way. I do suck it up and talk to her a little bit sometimes, just so there’s enough there that I don’t get bashed/gossiped about (also a small industry) but that’s it.

    1. londonedit*

      Wow, 6 years! Jane is nothing if not persistent. I’ve had to duck a couple of ex-colleagues in a similar way (also a small and gossipy industry) but usually the ‘Let’s catch up for a drink soon! Let’s go for lunch!’ stuff fades away after a few months of me saying ‘Oh, yes, we should sort something out’ and never actually committing. I’ve never had to keep it up for several years!

  38. Sick of Workplace Bullshit (she/her)*

    This grinds my gears to no end. This man is essentially a stalker, and the OP feels obligated to tiptoe around his feelings because of the nature of their past connection. I hate this so much.

    1. Alanna*

      Bob doesn’t sound like a good boss, and I get that OP is frustrated and wants less Bob in her life, but “essentially a stalker” seems like an extremely dramatic way to describe occasionally reaching out to a former employee.

      1. Tomato Soup*

        He’s been doing this for 3 years without response from op. Stalking might be the precise term but it is not benign.

        1. Peanut Hamper*

          Yep. There’s not a schedule for stalking (three times a week/four times a month/whatever). It’s the fact that he just won’t give up when LW is ignoring him. That’s very worrisome to me.

      2. Rainy*

        A dude once texted me about every six weeks for two years. I never once responded. That’s pretty analogous to what Bob is doing, and it’s definitely harassment.

      3. virago*

        I’ve been working in the same field, in the same small state, for over 30 years, and not once has a former boss ever reached out to me. Bob’s actions are a red flag rally.

      4. I have RBF*

        Still texting her after three years away from the old job? IMO it’s very stalkerish. It’s not “reaching out to a former employee”, it’s texting her for three years after no response.

        If someone texts me demanding a response after I’ve been ignoring them for even a year I would block them as a stalker, maybe even get a new phone number.

        I would be very creeped out by that.

  39. Mark*

    I would say, and it’s being honest for me because I really do feel this way, that when I move to a new employer, I don’t keep in touch with previous bosses. I think it’s healthier if both parties just move on. I’ve never once stayed in contact with prior managers/owners.

  40. crisper*

    I’m on Team Be Bland. I had a former manager complain to former colleagues that I hadn’t accepted his friend request. I generally felt no great need to stay connected to him socially, but I also had a low opinion of him (he’d strung me along for years with lies about trying So Very Hard to get me a raise and promotion because he was afraid of his boss and never actually asked her). So when former colleagues passed along to me that he felt bad about the snub, I simply said, “Oh, that’s too bad.” Pretends to be kind and is sufficiently bland that there was nothing to report back to him.

    1. Buffy Rosenberg*

      But keeping in touch with former employers/bosses is SO common, this just feels like so obviously an excuse that it would almost be better calmly giving the real reason.

  41. Peccy*

    You can get a lot of mileage from just being very vague and not engaging in hooks intended to draw out more conversation. You just kind of brush them off and don’t fully engage, not even engaging enough to tell them no. You don’t ask them any questions, you respond to any offers or suggestions with a vague ‘I’ll think about it’ and if you answer questions at all, it’s with one word answers.

    If you ride public transit you’ll recognize the conversational pattern of ‘person who doesn’t want to have a conversation and is being bothered by another rider’ lol

  42. Peanut Hamper*

    I actually changed my phone number when I left my last job. I sleep slightly better as a result.

  43. Apple Townes*

    LW, it seems like what you really want is for Bob to be held accountable for his poor management/judgment – hence the urge to spell out his failures to him in an email (hopefully writing in to AAM was therapeutic!). I think the fact that he is still getting away with all the BS that motivated you to leave that job ignites a flare of resentment every time you see his name in your inbox. I’d block him, just to keep him from living rent-free in your head for one minute longer – it’s been THREE. YEARS! I doubt your colleagues or boss care about your relationship with him at all — it doesn’t affect them, so why would they? If you cross paths with him in person, you can brush him off politely as Alison and others have suggested. And then exercise your right to forget he exists.

  44. Skippy*

    People know they sent messages. They never know if you *got* messages. You don’t have to lie and say you never got messages, but you can say, “I don’t even remember the last time I heard from Bob. That’s so weird that he’d say such a thing, but you know how he is.” Works better if you auto filter his messages into a never-checked folder.

  45. felis*

    Not an actual suggestion, just a fun little play on the suggested scripts, to amuse myself and hopefully some of you: “Oh, Bob, I’m so sorry I haven’t been responding to your messages, I’m just so terrible at keeping in touch with people I don’t want to keep in touch with.” delivered with the biggest smile and then just walk away before he realizes what you actually just said. That is how I would end the story in movie.

  46. JSPA*

    “Hi Bob–
    Is there some loose end that I left undone? I seem to be getting slammed by texts from oldjob– notably from you–while focusing hard on newjob. I’m a bit mystified, as I thought I’d been really intentional about getting things shipshape before leaving for new horizons / greener pastures. Things are going great at newjob! But it’s very next level. There’s so much to learn, so many new coworkers to meet. I really don’t have bandwidth for oldjob, unless there’s some very concrete simple question that comes up–in which case, send me an email, instead of blowing up my phone with texts, please!”

  47. Kat*

    When I’m sick I absolutely do not want to hear from ANYONE at work. A coworker sending me several texts over my leave would drive me insane. And the last person I want to hear from is my manager. It’s not unusual to let coworkers recover in peace. Some people want zero reminder of the work world. You are projecting what YOU want.

  48. PlainJane*

    In direct communication, I’d go with ignoring him as Allison suggests–it’s not worth prolonging the drama in your own life.

    What I wasn’t clear on was whether or not HR knows. LW says that people were discouraged from going to HR… does HR know that people are being discouraged from talking to them? Have the people leaving given the reasons for their departure? This is not LW’s responsibility at this point (and wasn’t before), and it would be awkward to alert them long after the fact, but during the time of employment, I would say that, if the workplace has become uncomfortable and it’s specifically because of the manager, please do go to HR. They might have been able to do something before it escalated this far, not least giving Bob a few pointers about his managerial style, or lack thereof.

    Bob also seems to be thinking of going 0-60 in about ten seconds, and therefore avoiding it. “I won’t fire him because his wife just had a baby!” seems like an odd response to “Dude just made a really offensive joke.” Firing would, presumably, be the last resort of behavior didn’t change after a reprimand… which is why you do the reprimand. It’s not going to go straight to being fired. Being, you know, MANAGED, would come before that, and then, if the behavior doesn’t change, or God forbid escalates, termination would go on the table, and would not be a surprise to anyone.

  49. CrazyPants*

    My old boss and I had a certain understanding, but she was also belittling to her underlings (i.e. everyone) to the point of being abusive. She retired and her replacement quickly distanced herself from the old guard. (We used to bring retirees in to help.)

    I’m afraid she thinks we’re friends of a sort. I hid a great deal of my actual personality because of the conservative nature of our workplace. So between not wanting to engage with abusive people and not having much in common with her, no, no thank you.

    She texted a couple times suggesting coffee but I know she just wants the dirt on her replacement. Things are being run differently (and I’m not necessarily in favor of all of it) but there’s no way in hell I would offer up my current boss’ success or lack of it to old boss.

    This article is helping me fret less about ignoring those texts.

  50. ProcessMeister*

    LW shouldn’t worry. Ex-boss telling people that LW is ignoring him will say more about ex-boss than it ever will about LW.

  51. Anonymous For Now*

    If someone tells the OP that “Bob” reached out to them whining about how the OP isn’t responding to their messages, I would suggest that the OP consider turning things around and asking the person if it doesn’t strike them as a bit odd that “Bob” is acting more like a dumped ex boyfriend than a former boss?

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