the 8 worst boss horror stories you’ve ever heard

by Alison Green on August 20, 2018

In the decade-plus I’ve been writing Ask a Manager, I’ve heard about some really bad bosses. Really bad ones. Picture the worst boss you’ve ever had, and these still might be worse. We’re not talking garden variety incompetence here – we’re talking wedding-crashing, organ-pilfering, horse-murdering bad.

At Slate, I’ve compiled the eight awful boss letters that still give me nightmares. You can read it here.

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  1. The Original K.*

    I didn’t remember the one about the boss who showed up at his employee’s wedding to ask a work question AND tried to have her written up for having him kicked out. That employee did the right thing by quitting!

    (I can see one of my previous bosses calling me on a Saturday not knowing or caring that it was my wedding day. She had a habit of waking people up on weekends with BS non-emergency issues. She wouldn’t have showed up though.)

    1. Bend & Snap*

      I got married when I was a super junior employee. My boss asked me for the number to the hotel where we were honeymooning and looked confused when I laughed.

    2. Kiki*

      My boss tried to rescind my vacation day that I took off for my wedding less than 2 weeks before the wedding, saying there was a very important meeting in the other office and I *had* to fly out that weekend. She was legitimately surprised when I told her no.

        1. Kiki*

          I got the cold shoulder when I returned and started getting “managed out”. I quit a few months later.

          1. AdAgencyChick*

            F@#!!! that noise!

            I hope that when you quit, it was for a way better gig, or that you found one shortly thereafter.

            1. Kiki*

              I don’t know if it’s “way better” but it definitely is better. A solid B on most days. :)

      2. Holly*

        How are people like that? It makes me so sad that there are people somehow have gotten so removed from reality that a meeting could be more important than a wedding.

        1. Antilles*

          The really ironic part is that in situations like this, there’s a very good chance that the other parties are much more sane and would therefore be straight up horrified to find out that your boss asked this. “You asked your employee to reschedule her wedding to come here? No! I am not okay with that, that’s ridiculous! What is wrong with you???”
          …But of course, I have zero doubt that the boss *didn’t* clear it with others and would have expected Kiki to not say anything about it.

          1. Observer*

            I’m sure that the boss didn’t clear it. But not because they are out of touch with reality, but because they are on a power trip.

      3. it_guy*

        My boss tried to send me out of the country for a very important meeting with a new partner. I would be returning (If it all worked right) hours before my wedding.

        He wasn’t terribly impressed when I told him that I couldn’t go. I said it’s easier to find a new job than a new wife.

        He didn’t make me go though.

        1. AdAgencyChick*

          “I said it’s easier to find a new job than a new wife.”

          BRAVO. I wish I had the presence of mind to be able to say smart things like that in response to completely insane requests instead of just being taken aback.

      4. kallisti*

        I got a promotion about a month before I got married and was told that because of my new position I could keep most of my pre-approved leave, but I couldn’t have one particular day off (the day I was getting married). When I asked why, I was told that too many other people had asked for that day, so I explained to my supervisor that most of them had asked off to attend my wedding. The supervisor told me to choose which one to uninvite.

    3. Annoyed Bride*

      When I was hired at a previous job, I negotiated time off for my wedding and honeymoon as part of my offer. (The wedding was over 6 months away, but I wanted it in writing because we’d already booked and paid for everything!)

      In the weeks week leading up to my less than two weeks off, I trained a temp to take my place for the 8 or 9 (I can’t remember now) work days I was going to miss. I also completed anything that could be done ahead of time and left lots of documentation for any “what if” scenarios.

      The day before I left, at the end of the day, my boss walks in to my office and tells me she is “concerned” about my absence and can I cancel or reschedule? My wedding. Which was that weekend. Yeah, no.

      1. Hills to Die on*

        She is a space alien from another planet and doesn’t understand what a wedding is. Or a schedule.

      2. Jadelyn*

        Good lord. I mean, I even use weddings as examples when I’m talking to new hires about being flexible about requesting PTO – I literally say, “If it’s at all possible, please be flexible when you request vacation time so that in case your boss has already given someone else the time off and needs you that week, they can give you the next week off instead or something. But of course, we understand if it’s something where the dates can’t be moved – like a wedding in the family or something – and in those cases, just please try to give your boss as much advance notice as possible so that they have forewarning and can juggle the branch staffing to cover those dates.”

        And that’s not even, you know, *that person’s* wedding I’m talking about, just a wedding they’re going to be attending as a guest. Where in the hell does someone get the idea that it’s okay to ask someone to cancel or reschedule THEIR OWN WEDDING???

      3. AdAgencyChick*

        I am just floored that there are two people replying here with stories about a boss trying to get you to move your wedding date that’s been long known and approved in advance, and that the OP from the wedding-crasher boss post isn’t the only one whose boss thinks it’s cool to bother you on your wedding day or honeymoon.

        Then again, one of my clients just came back from THEIR honeymoon…and they were in contact with us about one of their projects while they were away. I don’t think this was a mandate from their boss, I think this was them not trusting their colleagues to cover for them. (pronouns deliberately obscured)

        Sometimes people bring it on themselves…

        1. KHB*

          There was also a guy posting to reddit relationships last month wanting to reschedule HIS OWN wedding – with less than a week notice – so he could go to the World Cup final.

            1. Jerusha*

              I was about to say, that’s an excellent way to have the wedding rescheduled to the 47th of Never.

              1. londonedit*

                Yeah, if England had got to the World Cup final I’d have called my own wedding off just to watch it on TV, let alone if I had the chance to actually go to the match.

                1. Femme D'Afrique*

                  … and ALL your guests would have not only understood, they’d have breathed a sigh of relief, londonedit! The World Cup is serious business indeed!

        1. Annoyed Bride*

          A suggestion from my parents. Smart, smart advice from their years of managing and being managed. Their concern was that it was a long way off and people forget, but this is very important and non negotiable and not flexible, so make sure it’s written down.

      5. WellRed*

        Did she forget what the time off was for?? What did you say? What was her response?? Was she difficult in other ways?(I am guessing yes).

        2. Annoyed Bride*

          No, EVERYONE knew what it was for. They’d thrown me a wedding shower. She attended!

          I just stared when she said it for a beat or two. Then said, “Here’s all the documentation I prepared, I trained the temp. My counterpart in the department has copies of everything too, just in case. See you when I get back from my wedding!” It was literally the end of the day, as in I had my bag packed, jacket on, so I left. At that point, I didn’t care if they fired me, I was so over it. That was the moment I decided to find a new job.

          I realized later it came from her boss, who was the reason in my year there, turnover was almost 50% (in my field, that is a HUGE number!)

          1. babblemouth*

            Even if it came from her boss, her reaction on that request should have been “obviously I will not be asking OP to reschedule her wedding” not “oh, ok, I’ll see what I can do”. I expect some backbone from my managers.

      6. Annoyed Bride*

        It was a…special…place to work. Looking back through the lens of things that happened later, that request definitely came from above. My boss sheltered us as much as possible, but I can’t even imagine what happened above her (where the original time off request was approved, by the way!) to cause her to ask me to reschedule. Because boss’ boss did some crazy things that make some of the bosses in this article seems like a pleasure to work for!

    4. Nana*

      I was told we’d be coming into the busy season when I said I’d be out for two weeks for my May 3 wedding and honeymoon…and the boss asked me to delay…and we were (a not terribly busy) wholesale travel agency! I quit

    5. Theresa*

      I worked at a restaurant when I got married and my boss didn’t even come to my wedding. She went to Disney with a family friend instead (she was invited to my wedding first). Then we had our rehearsal dinner at the restaurant and they didn’t even give us much of a discount IMO. Idk I felt like we should have gotten the dinner for free or like 50% off. I had worked there for like 3 years.. They gave us like $100 off a $900 bill. But she didn’t communicate with the staff that we only wanted beer and wine and the servers let people order beer and wine. I told my family they could only have beer and wine and my husband didn’t so it was his family so I made my husband deal with that extra bill. LOL

  2. fposte*

    Horrible horse boss wasn’t really a horse-murderer, though; the mare almost certainly would have been put down anyway. What the boss did do is cause unnecessary suffering, especially to that poor horse.

    1. Akcipitrokulo*

      Horse boss got fired iirc. Which was something. And horse may have been able to have been saved earlier.

    2. ArtK*

      Are you a vet? Just like diagnosing people, we shouldn’t be diagnosing horses. Three hours is a big gap.

      2. fposte*

        The horse was already diagnosed, so I don’t need to; a 29-year-old mare (read–very old) with colic who would have required either expensive and draining surgery or euthanasia, and the OP’s vet has already said she would have put the horse down earlier.

        I’m not saying it doesn’t suck and the boss isn’t terrible (especially since it’s an animal industry, for god’s sake), but the boss really wasn’t the causal factor here.

        1. AK*

          Not to nitpick but I believe the vet thought the mare needed surgery, and we don’t know if OP would have been able to pay for it or not. If she’d been reached on the first call we can’t say what may have happened, and as far as OP’s emotions after the loss are concerned I feel like horse-murderer is a fair description in an anonymous discussion.

          1. fposte*

            For emotions, I agree, and I don’t really object to a bit of hyperbole here and there. But the OP said explicitly that the vet would have put her down if she’d known the OP wasn’t reachable, and the result of the necropsy showed a tumor that was beyond surgery. That’s after-the-fact knowledge, of course, and if things had shaded slightly differently I would absolutely have hung the horse’s death on the boss.

    3. Cucumberzucchini*

      No way of knowing that, and that one really upset me then and still does now as a horse owner. I would have be uncontrolled in my rage had that been my horse.

    4. Lalaroo*

      I’m wondering why you felt nitpicking that description was necessary or a productive comment?

      1. Ask a Manager* Post author

        Everyone, please stop chastising other commenters. There’s too much sniping and correcting others here. (I’ve been trying to call this out when I see it, but there will be a separate post coming on this at some point.)

        1. Lalaroo*

          I’m surprised to have been called out by you on this, Alison, since I really felt like fposte was nitpicking the language in a way that wasn’t helpful or adding to the conversation, and even seemed to diminish what happened to the letter writer. I know fposte is a really frequent commenter and you don’t know me, but it seems really weird that my one-sentence comment got me chastised like this. Seems backwards.

          1. Lalaroo*

            Sorry for double posting, but I’m frustrated. I mean, fposte started an entire thread correcting someone’s choice of words and my sentence gets a call out from the author? It really seems lopsided Alison!

    5. Horsey LW*

      He definitely didn’t kill her, but he did cause her to go through several hours of unnecessary suffering (and maybe at the start prevented us from attempting the operation [although at 29 and with the level of damage, who knows if she’d have made it]) and that’s what distressed me the most. At 29 I was well aware that she’d not last too much longer but to have her die in agony after suffering for as long as she did, that’s the killer. If she’d had a heart attack running across the paddock then it would have been incredibly sad but knowing how much she suffered at end, because some a-hole couldn’t take five minutes to pass a message on…

      I’ve had some time to come to terms with her death. Miss her fiercely but it’s amazing how much of my life was wrapped up in that lovely, fragile creature. I didn’t realise how much of it I’d put on hold while she’d been alive, especially in the later years. I didn’t like to travel or be away from her for more than 24 hours, and in the last year or so 12 hours. I spent a lot time obsessing over feeding, vet, dental and hoof care, probably too much really. It’s been nice to randomly decide to go somewhere for the weekend or splurge on a spa day. (and I’m finally at the point I’m not finding random bits of chaff in everything)

      After she died, I got a lot offers for free horses, I don’t think I want another one just yet (and maybe never). 15-30 odd years is a long time to spend with an animal and I’m not ready to make that commitment again.

      2. fposte*

        Hi, OP, I didn’t see this until late. I hope you don’t think I was belittling your experience; I’m a horsey person myself, and it really is just circumstance that saved him from being responsible–there absolutely would have been situations where he would have been.

        And I’m sorry for your loss. They are large-hearted creatures and they leave a large void when they go, even when it’s peaceful. When it’s a situation like yours, it’s just heartbreaking.

    6. 2horseygirls*

      Fposte, hindsight is always 20/20.

      FWIW, a friend had two colic surgeries done on her 35yo gelding 10 days apart at a nearby university veterinary hospital. It is up to each owner as to what action will be taken . . . but it is 1000% the OWNER’S choice – not the vet’s, nor the owner’s boss’ choice.

      There are further considerations if there are equine insurance policies in place – there is a sequence of events that need to occur in a specific order for insurance to cover the surgery, or (worst case scenario) for the policy to pay out in the event of the horse’s death.

      HorseyLW, again, my condolences on your loss.

      Not trying to pile on, but explain a bit further that there are additional factors or consequences that have not been mentioned.

      1. Le Sigh*

        Actually, boss was fired in that one. But the fact that OP lost their job was so awful and unfair.

        1. Detective Amy Santiago*

          He was? I thought that the boss who ordered the LW to leave the note got off scot-free.

    2. CM*

      To me, that makes that story the saddest — the OP also said in an update that everybody at the office thought she was a terrible person, and she knew she shouldn’t have done that, but she was also scared of losing her job (which she did anyway).

    3. I GOTS TO KNOW!!*

      IIRC the OP was very young and clearly didn’t know there were people she could reach out to in this situation. HR and her company made the absolute wrong call to blame her for not knowing what she couldn’t know having not been in the working world long.

      I was honestly really angry at all the people in the comments saying she deserved to get fired because she knew it was wrong. She was terrified of losing her job! She worked for a boss who would stoop to this level – how could she possibly know the company wouldn’t have his back on his behavior? He’s the boss. It’s not ridiculous for someone new to the working world to assume that he’d be supported.

      I feel so badly for the OP and I hope she’s doing well now. And I hope that company somehow caught wind of the letter here and sees how in the wrong they were for firing her when the blame here is with the manager.

      1. Kate R*

        I felt the same way. The OP said she didn’t have much of a work history outside of some college internships, so I assumed she was young and honestly didn’t know where to turn. IIRC, her second update said she had been doing some temp work and was hopeful something would turn into a full time position, which I hope happened. TBH, getting fired from this job might have been a blessing in disguise for her. It seemed like an office full of bees. The boss knew he was doing something dodgy (he initial told OP the letter was condolences), and HR should have communicated to her sooner that they are the resource if you think someone is doing something unethical. Even the coworker’s reaction seemed a bit out of line to me. I understand how upset she must have been, and I understand why she would have wanted the OP fired, but I can’t imagine calling clients to discuss any sort of personal matter at my company.

        1. Roja*

          Yeah, I still feel sick to my stomach when I think about it. IIRC, OP said she had to leave the industry entirely. And while I know this is going to come off as grief policing, calling up all of the company’s clients to personally inform them is just… so supremely not helpful. It was just a horrible situation for everyone involved, and it sounds like it will stay a bad situation for a long, long time. I hope I’m wrong though…

  4. Persimmons*

    HTH did the liver donor one not hit the news? A company-wide memo, people being let go over it…that’s an oddly tight-lipped set of employees.

    2. LCL*

      I always figured that someone spoke to someone at the medical facility involved in the transplant, and that was the end of it. Medical facility won’t say anything because of HIPAA.

      1. WellRed*

        The original poster is not bound by HIPAA and I’ve always wondered why there was no update.

  5. Estraven*

    I think Liver Boss still takes the cake, for firing people who wouldn’t be tested (even though they would certainly have been rejected as donors for assorted medical reasons/if they were under any kind of duress). Your personal heartbreak, Liver Boss, does not excuse your appalling behaviour.

    1. Bacon Pancakes*

      I need to re-read it, but I thought they let a pregnant woman go because she was also ineligible (which brings about a LOT of questions! How?!? YOU CAN’T FIRE PREGNANT WOMEN FOR BEING PREGNANT!!!)

        1. Bacon Pancakes*

          Not the OP but a woman in the office was fired because she was ineligible to donate due to her being pregnant. I think she would have had a screamin good case for workplace discrimination because her pregnancy excluded her from donating…. on top of all the generally banana-crackers stuff that was happening.

          1. Former Employee*

            And some people were ineligible because they had cancer at the time or previously, which sounds like they were being fired or threatened with being fired because they were cancer patients.

            The thing is, I supposed everyone could have humored the boss and volunteered and then let the medical professionals disqualify them for obvious reasons. They wouldn’t even bother testing the pregnant women, the cancer patients or former cancer patients, anyone with any sort of autoimmune disorder, blood disorder, etc. And for anyone who didn’t want to do it, as soon as they got to the medical testing phase, they could simply state that they were there under duress and they would be disqualified and no one would know why. The medical professionals would simply state that those people did not qualify.

  6. wayward*

    Just read about a Springfield, IL restaurant where the owner refused to allow a waitress who had visible bruises as the result of an assault work. Then she fired said waitress for not showing up and accused her of being a “good makeup artist” and faking the assault.

      1. wayward*

        It’s on Facebook, but AAM tends to not allow posting of links. Enter “Loukinens” and “Claudia Knight” (with quotation marks) in the Google’s search box, and the employee’s Facebook account should come up in the results. It was posted on Aug 15 .

        2. Kittymommy*

          Yes, thank you. I an now going to commence a good couple of hours if trilling this restaurant owner in every social media account I can remember I have.

          1. wayward*

            Figured the restaurant owner would be a strong candidate for Alison’s Bad Boss list if there was ever another edition.

  7. Nanc*

    Suddenly my boss’s annoying little foibles don’t seem so annoying anymore.

    I hope all of these letter writers are in better jobs with better bosses.

    1. Magenta Sky*

      I’ve been lucky, too, I guess. Worst boss I ever had fired me for taking a lunch, the day after he chewed me out for not taking a lunch.

        1. Magenta Sky*

          He definitely qualified as a horrible boss, and not just for that. (He was an HVAC contractor who had already been fined for violating California’s “prevailing wage” law before I started. He did not pay *me* prevailing wage on county jobs. He also tended to shout a lot, usually while eating his heart pills like they were candy. And when he fired me, he illegally delayed my final paycheck until the labor board got involved. And the other guy I worked with as nearly as bad.)

          But he wasn’t a tenth as bad as anybody on this list.

  9. JHunz*

    It must have been pretty hard to pick just 8. I guess excluding the letters whether the letter-writer is the horrible boss probably makes it a bit easier, since I imagine you don’t want to discourage people from writing in. But still, very spoiled for choice.

        1. KHB*

          I think that one was disqualified because the LW was the bad boss herself. I remember it being withheld from consideration for “worst boss of the year” for the same reason – Alison doesn’t want people to be afraid that if they write in with questions, they’ll end up subject to (too much) public shaming.

          1. Augusta Sugarbean*

            I really hope that over time that person was able to absorb the information from Alison and the comments. I can only imagine that her first reaction was defensiveness – I know I wouldn’t react well initially to an entire comment section saying “OMG awful!” but maybe after that died down, she was able to see how she mishandled that whole thing.

          2. Database Developer Dude*

            Except that boss SHOULD have been shamed, despite writing in. Who doesn’t let an employee attend their own college graduation?

      3. Foreign Octopus*

        That’s the letter that introduced me to AAM.

        Even now I’m still in awe of the boss’s blindness.

        I really wish we could get an update, or the woman’s POV.

      4. The Original K.*

        That one makes me angry every time I think about it. I REALLY hope that employee is somewhere in a job that makes her happy.

        Or the one who got herself and her entire team fired because she had created an “exclusive” team dynamic that lead to bullying and a star employee quitting. She did eventually see the error of her ways and wrote back in to say so, though.

        1. Comms Girl*

          Can we have a link for that one? I can’t remember if I’ve read it (although it does sound familiar, but then again there’s a letter similar to that almost every month). Thanks :)

        3. Michaela Westen*

          They were just discussing that one yesterday. First time I saw it. I was impressed the LW considered the advice she got here and made changes.

      6. Mallory Janis Ian*

        That letter still haunts me. The callous indifference of the boss to the impact her actions might have on a vulnerable young employee is painful to consider. I hope the person has found a decent place to work and has people in her life who uplift and support her.

        1. PB*

          Oh, goodness, yes. And she wanted to continue to badger that person, after she’d already left her employment! That letter made me so angry.

          1. Observer*

            Yeah, to me that was even worse. It was like he simply could NOT deal with the fact that this child of the foster care system had gotten so uppity that she actually had the audacity to be treated with basic respect and fairness, and so he needed to find some way to still harangue her.

            1. JustaTech*

              The amazing thing is that I’ve worked with people who’ve had a hard start in life, or been through really rough times, and they’ve pulled themselves through and gone to school or excelled in trade and are amazing, hard working people and the very best employees and coworkers. That anyone would look at them and go “eh” or “I need to chastise you for something that isn’t even wrong” is just plain stupid on the boss’ part.

  10. Anonamoose*

    The one I did think of that wasn’t on the list was the one where the boss was dating the employee’s father and wanted to do family therapy together. That’s a real boundary crossing nightmare.

    1. Not Maeby But Surely*

      Yeah, that one was particularly awful. I don’t remember if there was an update to that one or not, but I do remember feeling so sad for that OP. I hope she’s quit that dumpster fire and moved several states away with a new identity so she never has to see those people again.

    3. Hills to Die on*

      I still think about her. I hope she is doing well and is far, far away from her father’s girlfriend / boss.

    5. Sofie*

      The one I did think of that wasn’t on the list was the one where the boss was dating the employee’s father and wanted to do family therapy together.

      IIRC, it wasn’t family therapy. It was couples therapy, which just adds a layer of “AAaaaAAAAa!” to the general NOPE of the whole clusterfuck.

      … God, I hope that OP got the hell out of that situation. D:

  13. KHB*

    Assistant Manager Ned the chemotherapy crasher gets a lot of attention (and rightly so), but I think the main manager in that story, Robert, is just as bad. When Ned bullied the receptionist into giving him LW’s confidential calendar information, Robert’s response was to fire the receptionist and put Ned in charge of the employee calendars. Talk about a failure to manage.

  14. SDSMITH82*

    And I thought the a-hole boss I had back in 2012 was the worst. He said I had to either be at work or be fired when my then fiancee and now husband was in the ICU (and I had a note from his Doctor requesting my constant presence as he did better when I was there then when I was gone). This was after I caught him trying to find a replacement for my job (despite me being the top sales producer) and claiming “he just didn’t like me because I had the same hair color” as a former employee.

    For the record, I had both sick and vacation time to use- and he denied any access to both. He claimed his reasoning was that when his wife had elective surgery, she didn’t want him there, so why should my partner in ICU (Or his doctors) want me there?

    I already had one foot out the door- so that morning, I turned in my resignation and went back to the hospital. It’s the first, and ONLY time I’ve ever quit without having a job lined up, and left an employer hanging in the lurch. That man had so much darkness in his soul, just leaving that place was a burden lifted (even without a job).

    1. lnelson1218*

      And for people/bosses like that that is all they often deserve. They won’t be showing you any loyalty or consideration.

      1. SDSMITH82*

        AGREED! I filed unemployment due to the fact that I was basically forced to quit and found out that he’d intimidated all the other employees to lying about why I left. He did the same when I filed a very justified complaint for unpaid overtime (with records I’d sent myself long before it came down to me quitting) and used his minor celebrity to his advantage. He then fired/forced everyone to quit within 18 months of me leaving and called them “untrustworthy” because they were willing to lie to keep their jobs.

        There really is a special place in hell for that man and people like him.

        1. Bea*

          Holy….what a sociopathic monster. I’m relieved you walked out and got away from that nutjob.

    2. Editor Person*

      when his wife had elective surgery, she didn’t want him there

      Gosh, boggles the mind. /s

    3. ToS*

      For those reading along, if the employer is large enough, FMLA protects leave use for situations when your spouse or dependent has serious health issues. Of course it helps when HR can back you & management up and show terrible bosses how to change with the times. It doesn’t guarantee you will be paid. Or that your boss will turn over a new leaf, but it can help work be a little less terrible by protecting your time off.

    4. Michaela Westen*

      Um – isn’t denying access to sick and vacation time you’ve earned illegal? I hope they were included in your last check, at least!

  15. Cait*

    Oooh such a good list!

    The LW who wrote in after being demoted? or maybe fired because he didn’t think a slightly older team member was a good fit for his team was also a special one. If I recall, his boss had hired her for special projects and the LW kept reassigning them to other team members because he liked them better. The level of denial in that letter still sticks with me today.

    1. Anon Accountant*

      Is this the manager who allowed beer runs? If so that manager was fired along with their entire team when the employee who was treated poorly gave an exit interview regarding that department.

        1. C in the Hood*

          That was the Un-Manager, who did eventually come to realize that what they did was wrong, and did start turning their life around once their attitude changed.

        2. PSB*

          Allison consistently referred to that OP as “her,” so I’ve always pictured her as a woman too.

  16. lnelson1218*

    For many years, I thought that my worse boss was a “lady” who was the office manager. A bit of a bullying. I was new to the field and making rookie mistakes, but she wasn’t easy to work for. Personally I don’t consider it a badge of honor when your assistant turnover rate is close to 70%.
    Then fast forward many years and several job changes later (had some really good bosses in between). A new VP was hired. He was a piece of work. Bully sums it up nicely. Not kidding on the way into the office one day there was an article in the subway paper “How to recognize the office bully”. This guy ticked off 7 of the 11 points. Showed no respect for other, no appreciation. Maybe he thought that he would die of a heart attack if he uttered the words “thank-you” Even when someone helped him way outside of “job description”
    The best is probably when he asked the office manager whose food was in the tuperware, because it was good. When confronted about eating other people’s food (many of us brought in lunch), he said that it was our fault that he ate it since we brought said food in.The office provided snack and bread. There was no excuse for helping himself to others’ food. Names were on lunch bags.
    When the lay-offs came, I made sure that I was laid off vs. having to work for this jerk directly. I would have gotten myself fired when I told him where to go when he yelled at me.

    1. Kroatoan*

      Im going to use that on my kids.

      “Oh no! You must be cursed to die if you cant say thank you to your mother! Thats terrible! It must be so difficult for you! Im glad you are holding out, it would crush me to lose you. ”

      Well. Not directly, cause they dont have that sense of humor. But to my mom friends when i vent for sure.

  17. Elmyra Duff*

    OldBoss at OldJob started one of my annual reviews (which also included two supervisors and the training manager in the room with us) by saying, “You’re our best teapot painter, but we really just don’t like you personally.” And that was one of the nicer ones after hearing about other people’s reviews with her that year. We all bonded over having to go cry in the bathroom for 10 minutes after our meetings were over. It was an excellent team building exercise.

    1. Bend & Snap*

      I had one of these too. “You’re doing a good job but nobody likes you.” It really meant that HE didn’t like me and I quit a couple of months later.

      That job resulted in many psychological scars.

    2. Monty's Mom*

      I’m so sad and mad at this! This is terrible! Is OldBoss still there, being terrible?! I’m really hoping you are having a better experience where you’re at now!

      1. Elmyra Duff*

        She eventually fired me for literally no reason. (Gotta love living in a right-to-work state!) Eventually, the company was bought out and almost the entire department quit. I have no idea if she’s still there or not, but I hope she’s miserable, wherever she is.

          2. Yikes*

            It’s also possible that had the poster been allowed to unionize, they would have benefited from union protection.

    3. BookishMiss*

      “You’re a good employee, but you have a bitchy aura.”

      Favorite feedback of all time.

      1. Detective Amy Santiago*

        My mom got fired for “not being a team player” at the company where she would volunteer her time to dress up as a clown when they put on family events.

    5. MatKnifeNinja*

      My Aspie cousin has gotten that sentence at three of his old jobs.

      “We are firing you, because if we don’t, three other team members will quit.”

      He had no clue. Hearing that three other humans hated you so much and are willing to quit is awful.

    6. Michaela Westen*

      “You do good work and your colleagues like you and you fit in well, but…”
      I don’t remember what came after the but. It made no sense at all. She was always looking for a fight/reasons to abuse.

  18. Goya de la Mancha*

    EVERY. TIME. one of these posts comes up I want to go and hug my boss and kiss her feet for all the issues and quirks I have with her. Because I will take those ANY day over a boss like these!

  19. EditorInChief*

    All these stories make my worst ever grandboss look like Boss of the Year in comparison.

    For some reason she couldn’t be bothered to learn any of the names of the men in our department and enjoyed randomly firing them. One day she demanded my boss fire Pete, which he did. He had absolutely no backbone and would throw anyone under the bus to save his own skin. A few weeks later grand boss sees “Pete” in the office, and demands to know why he wasn’t fired. “That is Ted, not Pete,” said my spineless boss. “Oh,” said grandboss. “Well, just as long as someone was fired.”

    2. Hapless Bureaucrat*

      That’s an almost cartoonish level of jerkishness. It also suggests that the boss could have just renamed Pete something else, maybe given him a fake moustache, and been just fine.

      1. Antilles*

        That was my thought too – an old-school sitcom style where you ‘fire him’, then hire a ‘new guy’ with a fake beard and like, one letter different in the name. “I fired Pete, just like you asked. But since we did need a teapot analyst, I managed to find an excellent candidate. His name is, uh, Qete, so we call him ‘Q’ for short.”

        1. Deejay*

          There’s a video about Death Star officers doing this. When Darth Vader does his “You have failed me for the last time” thing, they only act as if they’re being Force-choked to death and come back later with a different name.

      2. EditorInChief*

        She was a complete moron. “Pete” probably could have come back in disguise. But my boss was complicit in all the bs there by being a spineless jellyfish. I do have to thank both of them though, because they taught me everything I needed to know on how NOT to manage a team. As a manager now I can’t even imagine conducting myself the way either of them did.

        About a year after I left that hellhole I found out that she had been fired for “misuse of company resources”. A former coworker told me security and head of HR appeared in grandboss’s office, and she left with them, never to be seen again. By the next morning her office had been cleared out. One of those rare times when Karma actually manifested itself.

    3. Bea*

      And I thought my old boss was bad about firing whimsically. At least he always had a shallow but somewhat reasonable reason.

      Every time a future employer asks if I could handle firing or layoffs of staff, I’m able to say it wouldn’t be my first rodeo. Sigh.

    4. Nana*

      In a(n unauthorized) biography of J. Edgar Hoover…he once demanded that someone be fired from a new class of incoming FBI men “He looks like a truck driver.” Uncertain who that was, the trainer fired several men.

  20. k.k*

    It baffles me that there are people that think being the boss makes them all powerful, or that they’re employees should prioritize work above all else. If you’re a surgeon and currently have someone’s organ in your hand, or your job effects the fate of the worlds nuclean aresonal… then okay. But nobody’s canceling their wedding so you can get that TPS report on time.

    1. PlainJane*

      This. Yet I see the “work before everything” all over the place, at least in the US. I enjoy my work, and I’m the primary breadwinner and source of the family health insurance, so work is really important. But it isn’t the most important thing in my life. Besides, I find that employees with outside interests and balanced lives are usually more productive and pleasant than the, “work is everything,” types.

    2. Bea*

      From the stories of what readers have gone through here, I’m not surprised at all. Look at every letter that basically ends up with all of us begging the writer to run away.

      They get away with these sick demands. So anyone on a power trip has a delightful time ripping apart their employees and so many feel stuck in the hell they’ve found themselves in.

    3. Michaela Westen*

      I think there are cultural things that play into that.
      1. Since the elites are trying to take all the money, people are afraid they won’t be able to get a job with decent pay and benefits if they leave their current job.
      2. In many parts of America, there is nothing to do but work, eat, or go to church. So people look for all or most of their life fulfillment at work.
      We desperately need cultural changes to help improve things.

  21. Frankie Bergstein*

    On a work trip in a non-English-speaking country that didn’t have a strong mental health care system. A colleague was having a psychotic break (according to a mental health professional), and I had to escort her back to her home (this included ensuring she did not run away at various airports!). The company had health insurance for travel abroad, but didn’t like to tell people about it in case they used it.

    AND, separately:

    I wanted to go to a wedding on my husband’s side to meet his relatives for the first time. Despite 3+ months of notice, my boss had me rearrange our work calendar to accommodate their vacation, grandboss’ vacation, and colleague’s vacation… but I couldn’t go to my husband’s family wedding.

    2. BeenThere*

      Yeah… I hear you… I had a boss ask me to withdraw my vacation (a long weekend over the Labor Day weekend, so really just a couple extra days) because we were “so busy.” So I did. She then promptly took vacation over that time period. I quit a few months later (and now have a fab boss).
      (She couldn’t outright deny my vacation or would have had to justify it. “Because I want to take vacation then” is not a good justification. Had I realized what she was up to, I would have refused to withdraw it.)

  22. stitchinthyme*

    Not quite in the same league as some of these, but my worst boss:
    * Tried to make me sign an agreement to pay back the $20,000 recruiter’s fee unless I stayed at least a year. (I turned the original offer down and later accepted it when he agreed to drop that.)
    * Tried to talk a coworker out of a necessary gallbladder surgery because of the cost to the company health insurance.
    * Refused to give regular raises (though annual increases are standard for this industry) and only offered raises when he felt like it or when people gave notice (no one took the offers – including me).
    * Yelled at another coworker when he missed work due to being hospitalized. (Yes, he had called in. And came back before his doctor said he should.)
    * When I asked for performance feedback, his response was, “If I have a problem with your work, I’ll let you know.”
    * Refused to even issue a reprimand when a coworker accused me of being anti-[his religion] because I had — with our project leader’s permission — made a small change to his code while he wasn’t there.

    1. stitchinthyme*

      Oh, and of course, when I did give my notice, I got THE WORST guilt trip I’ve ever experience when leaving a job.

    1. Memily*

      I didn’t see one in the comments there. I really hope that OP is doing OK and that their parent company was horrified at what had happened.

    2. MommaChem*

      There was an update. IIRC the OP was able to use some of the suggested phrasing to get their boss to back off being so hands on. They shared some additional info that made the boss’s overreach a bit more understandable, but still really weird and uncomfortable. As a bonus OP’s sister turned 18, got tested to donate, and was a match! It was a total surprise cause they were both (again iirc) adopted and didn’t think a match was likely. Latest update I saw, both OP and sister were recovering well from the transplant!

        1. AgnomenGnome*

          Yeah, that’s the boss offering to donate a kidney letter. I don’t think the chemo one had an update. I really wanna know what happened with that one!

      2. Middle School Teacher*

        I think you’re thinking of boss who wanted to donate a kidney, not Chemo-busting Ned.

  24. A username for this site*

    I had a boss, in the middle of a training full of white women, run by someone two levels above him who was also a white woman, announce that he does not like working with white women.

    1. you don't know me*

      I was once in a meeting with my manager and he was complaining about one of the ladies deciding not to come back after her maternity leave. He said something like “that’s what happens with these women. They get married and have a baby and then they don’t want to work anymore.” Then he looked around the room full of women, realized his mistake and said something like “well maybe this isn’t the best time to talk about that.”

      No, no its not.

      2. Meghan*

        Gosh, I wonder why they wouldn’t want to come back to that environment when given even the slightest excuse not to.

      3. SadieMae*

        I had a boss who agreed to an employee’s maternity leave request of 6 weeks off and then 4 weeks half-time work to ease back in. 2 weeks into her leave (literally 2 weeks after she endured a very traumatic labor and emergency c-section), he started insisting we call her/email her to do things from home (he had hired a friend’s daughter to fill in, as a favor, and the friend’s daughter was completely unqualified). When she refused, he started calling her himself and getting upset when she reminded him she was still on maternity leave. At the six-week mark, when she started coming into the office 20 hours a week, he would harangue her about “leaving early all the time” (even though they had agreed to that before the birth).

        She was so angry that she quit the job entirely, and then he smirked to all his male colleagues about how women always just wanted to stay home with their babies and how they just weren’t dedicated to their jobs and maternity leave was all a scam, etc.

        I’m happy to report the woman in question landed, soon after, a more flexible job that paid nearly twice as much!

        1. Comms Girl*

          Grounds for discrimination right there. Jeez :/ Glad to know she found a much better job (and you too, by the looks of it :) )

      4. Batty Twerp*

        At the risk of getting slated, I think he deserves a bit of credit for being self-aware enough to realise that he said the wrong thing. I can think of at least a dozen bosses (both directly in my experience, and anecdotally) who would not have realised their faux pas and been outraged that anyone was insulted by such a comment.

        2. Le Sigh*

          I’d give him more credit for never having said it. If that was a room full of men he wouldn’t have corrected himself. He only seemed to notice it was a problem because he did it in front of women. “Oh no, they heard what we really think!”

      5. Lynne*

        I was in a meeting with a vendor who came right out and said something like that…IIRC it was about a previous assistant having gotten pregnant and quit, so this time he hired an older woman so that wouldn’t happen. He chuckled at his cleverness.

        Every person from my org at that meeting was female. Cue uncomfortable silence while everyone on my side all sort of looked at each other. I think Vendor Dude was so oblivious he didn’t even notice our reaction.

        (And there are people out there who think we have gender equality already and the need for feminism is gone……sigh.)

  25. Chloe*

    Remember the boss who made his employee come pick him up at the airport at 3 am and then wrote her up for not being properly attired? That one still sticks in my craw.

      1. Chocolate Teapot*

        And wasn’t there a letter around the same time about a boss getting very drunk at a business luncheon and asking the employee to drive him back to the office, except the employee couldn’t drive for medical reasons? That one ended with employee being fired and difficulties in finding a new job because the boss was badmouthing employee to all his cronies.

        Was there ever an update for that one?

    4. stitchinthyme*

      I think my other favorite good-ending one was the one from the guy whose lunch thief accused him of deliberately poisoning his food; even though he demonstrated that he actually liked his food extra-spicy, he still got fired for it…but after he had his lawyer send them a letter, they investigated and found that the lunch thief and the HR person who fired him were most likely having an affair, and the two of them both ended up getting fired, while the LW got hired back with a raise and an apology.

      1. MoodyMoody*

        That wasn’t a bad boss story. The manager had his back after the lawyer contacted the company. The HR woman dating the lunch thief took it on herself to fire Mr. Spicy. But the story was full of good karma and Schadenfreude.

  26. Temperance*

    Honestly, the bird attack boss/company stuck out to me as one of the worst, but I understand why it wasn’t included, since the attack victim wasn’t the one who wrote in.

      1. SSS*

        Oh holy cow, I worked for a firm where the son of the partner had a small parrot. The guy would not get a law license because of how much he alienated many, many lawyers with, for example, insulting language in letters that enclosed torn up settlement checks because he had changed his mind.

        Anyhoo. I have no parrot experience. He’s all, oh, the bird is greeeaat – and places it on my sleeve. It proceeds to walk up my arm and bite me twice (neck and ear) before a different lawyer gets it off of me, while I’m holding back tears and the impulse to bodily grab the bird and fling it in self-defense.

        This was decades ago. The large cage made his office awful between cleanings. I hear parrots can live longer than humans…

  27. The Tin Man*

    The boss who wanted 20% of the next salary had one of my all-time favorite responses from Alison, with

    “Sure, it’s legal for him to ask for it, just like it’s legal for him to ask for your first-born child or a lock of your hair.
    It’s also legal for you to laugh and laugh and laugh, and give him nothing — no child, no hair, and no money.”

  28. MrsRamsey*

    This is not as bad as some bosses but a former job was very toxic. My boss was forever making comments about people’s finances. How much is your car payment,etc. I used to be able to work from home some. The morning I found out my mother died I went into the office to hand off some files I had been working on before leaving town for the funeral. 6:30 in the morning with an 8 hour drive in front of me in winter weather, there is my boss in the office dancing up and down and saying ” Oh, now you’ll be getting an inheritance.” No drive safe, do you need anything, can we help, I’m sorry about your mother. At this point I had worked there for over 8 years. Unbelievable.

    1. tangerineRose*

      ” Oh, now you’ll be getting an inheritance.” Wow. That’s probably what the boss thinks will happen when his mom dies. Hope she knows that so she’ll disinherit him/her.

  29. SSS*

    So glad you said “former job” – that is a huge time-to-move-on sign.

    I’m sorry about your mom. She’d be proud of you moving on.

  30. RedinSC*

    Oh, I always like to share my bad boss story! I was working in high tech in silicon valley during the tech bubble of the late 1990s early 2000s. After 9/11 the economy and the tech bubble burst and we were laying off all kinds of people, off shoring jobs, etc. During this time (I was with the company for 4 years or so) I had reported to something like 4 different VPs and maybe 7 or so directors. I was kinda over it, and I had been managing the team for long enough that I wasn’t current on the tech skills so I had my name on the list of people to be let go in the next round.
    New VP started, he was kinda creepy, but also, like I said, I was over it, so I really just didn’t put much energy into training up. Turns out I was laid off a month later, so all worked well.
    Where’s the bad boss part, right? About a year later a friend called me up and said I needed to watch 20/20. OMG! It was my boss, he was accused of killing his estranged wife’s boyfriend AND burning up his porche. The only reason this all happened was because at this time CA was recalling the governor and all kinds of weirdos decided to run. This guy also decided to run and the cops in his original city saw this, looked back into the case. There had been enough technological advances by then that they knew he’d done it. He got extradited back to his state, tried and is in jail now, for murder.
    So, in these bad boss story sharings, I always get to say, YUP! I worked for a convicted murderer!

    That’s also the TL:DR version – I worked for a murderer

      1. RedinSC*

        I was just thinking that dude, you committed murder, and got away with it, DON”T put yourself in the public eye! I suspect the cops probably woudln’t have really done much (over worked and all) with a cold case like that, but when you run for governor, you’re going to get some attention.

      1. RedinSC*

        Ha, really? That’s amazing. There’s still people out there who are saying he was framed or at least innocent, etc. IDK, it was just so surreal.

        1. ihearditbothways*

          It was his family who thinks he is innocent – no surprise there. But I think by the end of the episode they were at least willing to consider that he might not be innocent after all. The evidence against his is pretty damning. He knew the guy was shot/stabbed (can’t remember which) before the police investigating did.

    3. Eligibleforrefunds*

      I had been working for about a year at at a small company, when my manager/company owner went out of town on business. That was when the FBI showed up asking questions about her ex-husband. He was on the lam and the FBI believed she was in contact with him and might know where to find him. (She was, and she did -she took his calls in an open-floorplan office) She told them she had not heard from them in years.

  31. Fishcakes*

    My last boss felt entitled to inside privacy like boss #3 in the article. She had another employee monitor our emails (he was a personal friend and did nonrwal work). It was supposed to be a secret but he’d bring it up slyly to bully people. Cameras were recording us at all times and our internet use was monitored. I got taken to task for browsing stock image sites, which was part of my job.

  32. Christopher*

    I had an HR Manager who expected me to be ready to work a (heavy labor) graveyard shift right before going in for brain surgery to remove a large tumour. He was also puzzled why I needed a minimum of a month to recover and thought I could return after only a few days. Fracking moron!

    1. SadieMae*

      I had to have a lumpectomy a few years ago, under general anesthetic since the suspect area was very deep in the breast, and my boss wanted to know if I was sure I couldn’t just come back to the office later that day. This was on a Friday, I was back to work on Monday, and you would have thought I’d taken a month off after getting a tooth pulled or something. Sigh.

      1. Sabina*

        What is it with moron bosses and medical stuff? I had a boss whine and badger me into coming into the office while I was on medical leave to type a personal letter for him. He didn’t want to ask anyone else to do it because he didn’t want it known that he used his assistant to handle his personal business. After I drug myself in and typed his stupid letter he remarked to another woman in the office that I had looked kind of out of it. She replied that it was probably because I had just had major surgery for a life-threatening condition and that’s why I was on MEDICAL LEAVE.

        1. AsItIs*

          Moron + selfish.

          Some people are going to be mighty ticked off when the centre of the Universe is discovered and they’re not it.

      2. Amanda*

        I’m so grateful to have a reasonable boss. He could have forced me to re-reschedule a time sensitive doctors appointment for a third last minute work trip in as many weeks, but he is allowing me to teleconference instead.

    2. MrsRamsey*

      I hope you are fully recovered from that surgery. Wishing you the best, and hope you have been able to move on to something better.

    3. CupcakeCounter*

      Then there is my idiot husband who thought he could go back to work Monday after a double inguniel hernia repair on Friday. His doctor and I had a good laugh about it and I hid his keys for a week.

      Now that I think about it he IS a manager…

      1. Cakeismyspirtanimal*

        Ha! My partner had a hiatal hernia repair and his doctor told him he could go back to work in 1-2 days! Did. not. happen. The anesthesia alone made him too sick to work the next day, not to mention it is hard to work if you are bent over at the waist and every movement is painful.

  34. Doctor Schmoctor*

    My worst bosses were .. not great managers. The ones on this list are just horrible people.
    We were working on an engineering project for a mine, and everybody working on site has to undergo an annual medical exam and induction (required by law). Any contractors on a mining site has to pay an amount for each person they send for the medical, and that person’s manager has to authorise it. When I had to get my stuff renewed my manager didn’t approve it, because he wanted me at the office, because one of our drafters resigned, and he needed me to “help out with drawings”. It’s not my job, but I have access to the drafting software. So I wasn’t actually involved in the project at all and didn’t get any exposure because boss needed me to do someone else’s job, and the company is too stingy to hire someone to do it. Meanwhile they hired a new guy to do MY job (the job that I was hired to do in the first place!). New guy eventually disappeared one day, and stole a ton of confidential files.

    And at the end of the year I got a 3% increase, while the other guys got 5 or 6%, because “you didn’t really do much this year.”

    That’s my worst boss story.

  35. Bagpuss*

    Ooof. I’ve never had a boss as bad as these. My worst was in the first job I had after I had finished my professional training and moved on to a new company. We were a small branch office so there were just four of us – Boss (Partner in the business) me, and 2 secretaries.
    Boss used to lose his temper a lot and would then loudly tell clients what terrible employees we were. At one point, his secretary noticed that he had cancelled or rearranged every appointment which had gone into his diary for a Friday afternoon, over a period of about 5 weeks, so she (reasonably enough) asked him if he wanted her to avoid making appointments on Friday afternoons. He lost his temper (I assume he thought she was accusing him of leaving early, which (a) she wasn’t and (b) he was perfectly entitled to do if he wanted, it was his business). He picked up the diary (A4 size, hard cover) and threw it at her. Then half an hour later was telling clients and one of his business partners that she had “stormed into his office” and thrown the diary at him.

    He used to scream and shout and us and then if anyone lost their temper would discipline them for shouting at the boss.

    It took me years to get over the impact of working for him. I wish I had left so much sooner, but as I was young and inexperienced, and it was the middle of a very tough time in my industry, I spent a Long time thinking that maybe this was how workplaces are, and that Id just been lucky in my first job.

    (the manager at my next job was in many ways a terrible manager and all about style over substance, but I was forever grateful for the way he dealt with a major error I made about 2 months into the job, as it was such a refreshing change. – instead of yelling at my, or firing me, which was what I was expected, his initial response was “OK, it sounds like you’ve done all the right things so far to deal with this, and you were right to come to me with it. Here’s what we need to do now, it’s not great but I’m sure we can sort things out” – the fact that he treated it as ‘our problem’ not ‘your mistake’, and focused on fixing it not disciplining me was a huge revelation. In that way, at least, I’ve tried to be his kind of boss, once I got to a more senior role myself.

    1. Observer*

      I’m trying to wrap my head around someone not quitting after a boss throws something like that at them. Normally, you figure that the people who stay just don’t have many options, but she sounds like the kind of person a good boss would treasure.

      1. Michaela Westen*

        Maybe she didn’t realize that, or they lived in a place that didn’t have many jobs. The place I grew up in was like that. I knew if I messed up, there might not be other jobs. That’s one of the reasons I moved to the big city.

        1. Observer*

          That’s really sad. It’s bad when anyone gets trapped with an abusive boss. When it’s someone who is clearly a good employee, it’s worse.

          1. IDontRememberWhatNameIUsedBefore*

            The more horror stories I read on here about abusive bosses that people can’t escape from because they will have no means of supporting themselves, the more I am convinced that we need things like Universal Basic Income and other social safety nets.

  36. In a better place now*

    I’ve never sent this one in (I escaped toxic badjob a while ago now), but the manager there cut a cancer-survivor’s hours to part time so that she’d no longer be eligible for health insurance.

  37. Rey Mehlhorn*

    Worst one I’ve had, there were red flags towards the beginning. I was hired to work in the office of a larger building, which he then sold within 2 months of hiring me. I have to assume either a) He had some idea in advance things were going that way and just didn’t tell me until right as it was happening or b) He was really that short-sighted in his business practices that he did not expect to have to sell the building. Either is plausible. My office became the computer and fax/printer jammed into the corner of his dry-cleaning building, next to steam vents. There was no AC. The fax/printer broke and the computer kept shutting itself down due to overheating and he asked me could I make it not do that, to which I had to explain the computer shuts down from overheating because the alternative is catching fire, possibly. Same boss had me train initially under his wife, who was a vibrant, smart woman who told me about how she had started and run her own successful business, but sold it when they got married. Except that whenever he was in the room, she would suddenly become a much quieter, meeker, uncertain person who could not ever get anything right, according to him.
    As his sole ‘office’ person, I was privy to things his other employees weren’t, such as his practice of not paying bills until utilities were at the point of threatening to shut him off. He harrassed people into quitting when he wanted to fire them, because he didn’t want to pay unemployment. He also asked me if job applicants- who I had only spoken to by phone- were black. I said ‘how would I know and why would it matter?’ His response: ‘Well did they *sound* black?’ He wanted only black women working in the back, white women for the front counter, and white men as drivers. I was younger then, and it is the lowest point of my working career, I would not put up with now what I did then.

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