The worst bosses of all time

icon1 //Posted by denised in Bad Boss Stories, Featured Articles on | 13 responses

Last week The Huff Post featured a list of what they consider to be the worst bosses of all time. I think the only reason my last boss didn’t make the list is that he didn’t meet the height requirement. Here are some bosses who did make the cut:

  • Anna Wintour – She’s got everyone in the fashion industry hanging on her every word and she’s so bad, she even had a book and movie made about her really bad boss ways
  • Lenny Dykstra – The former professional baseball player launched a publication a couple of years ago to help teach young athletes to invest wisely. Instead Dykstra swindled employees into using their credit cards to pay for fuel for his private jets. Nice.
  • Scott Rudin – I think when you tell an employee “The only thing separating my hands from your neck is the fact that there are 3000 miles between us”  you might be a really bad boss.

To see the Huff Post’s entire list, click here. If you’d like to nominate your boss as one of the worst bosses of all time, leave your comment (anonymously if you’d like) in the comment section of this post, or send an email to denised@reallybadboss.com.

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  • Pingback: More worst bosses of all time – Another reader submits her story | Really Bad Boss

  • http://reallybadboss.com denised2

    WHAT? What a story!! I can't believe she actually slapped her assistant in the face??! That is insane! You know it's time to get moving when you start becoming physically ill because of a job. Your former boss now qualifies as one of THE worst, if not the worst boss stories we've received. Look for it to be posted (anonymously) sometime next week. Thanks for sharing, and if you haven't found anything new yet, hope you find something really soon.

  • http://reallybadboss.com denised2

    WHAT? What a story!! I can't believe she actually slapped her assistant in the face??! That is insane! You know it's time to get moving when you start becoming physically ill because of a job. Your former boss now qualifies as one of THE worst, if not the worst boss stories we've received. Look for it to be posted (anonymously) sometime next week. Thanks for sharing, and if you haven't found anything new yet, hope you find something really soon.

  • MegMurphy

    Last year, my company slashed our salaries by a great deal without warning. Since I wasn't making much to begin with, this was a devestating blow to me financially. I began to interview and when I recieved an offer for substanitally more than I was making at the time, plus overtime, I jumped at it. There were red flags from the beggining, I didn't meet with the President or the Director until I started. At first, it was the Director who was making my life miserable. Giving me huge projects I wasn't familiar with and didn't have the tools to complete. I literally did not have the software on my computer to finish these projects but was told to improvise. At the time, I had no idea how good I had it because once the President got a hold of me, my life was pure hell. The President was a large woman, both in size and height, with a voice that sounded like nails on a chalkboard. During my first week there, I saw here slap her assistant in the face, twice, with a checkbook for some percieved mistake. As I began to work more closely with her, I realized everything you did was wrong to her. You had to write a formal memo explaning everything and she wouldn't talk about things via email. You literally had to write a memo saying, attached are the labels you wanted me to give you. I would go through 10-20 drafts of any document, she would edit them with a pen and noone could read her handwriting. I worked 14 hours day plus weekends and holidays (even Christmas). Any time off you requested would be denied or revoked when the President was in a bad mood (towards the end you had to ask for weekends and holidays off, even though we were closed). I was once kept there till 1am doing a ridiculous project (she loved to make the simplest tasks difficult) and told I couldn't go home or I and my deparment (who has all gone home at a normal time) would be fired. She would tell the entire office that we wouldn't get certain holidays off if my manager and I didn't finish a certain project on time. I am a petite woman and she was literally a foot taller than me, she would get within a inch of my face and scream at the top of her lungs for the smallest percieved mistake. My blood pressure went through the roof, my hair began to fall out, I couldn't sleep, I wold vomit due to anxiety, and had frequent panic attacks. When I had a emotionla breakdown at work, she seemed somewhat sympathic at the time but told me “little white girls” couldn't sue her for harrasment because we weren't part of the protected class. Then on Monday, she called me into her office and told me how my emotional outburst ruined her weekend because if made her feel guilty which she shouldn't because the whole thing is my fault. The final straw came on the day when she called me into her office and told me that the Board would be in town the next day, she would be really stressed so she would be yelling at my alot. She wouldn't be able to do so in front of the Board so she wanted me to think of a signal she could give me that would let me know to go to the back alley behind the building where she could yell at me there. Also in that week, I was told to tell her when I was going to the bathroom and if she was busy, she gave me a whole chain of command of people to tell I was going to the bathroom. I left my letter and took off. I should also note, I was not in an administrative position, there was no HR deparment and she controlled everything. Later I found out she hit her assistant in the face with a text book!

  • http://reallybadboss.com denised2

    FYI, your comment is now a featured article on the site. You've even got a few comments. You can read the post here … http://reallybadboss.com/2010/01/a-bad-boss-fro…

  • http://reallybadboss.com denised2

    Glad the story helps, and that's a great tip. I've seen it done and done it myself. People will think you're crazy and they tend to leave crazy folks alone. Thanks for commenting and good luck with your own bad boss.

  • Name

    This story does help me. I thought my boss was bad. One thing I try (it has turned into a little game with me) is that every time I get mad at my boss, I smile real big. I will not let anyone know that he gets to me. I've also seen people play dumb … it is amazing how mad that makes the boss. Good luck and thanks for the story.

  • http://reallybadboss.com denised2

    I definitely want to use it – we'll keep it anonymous of course. You never know maybe someone will offer some advice that will help and maybe reading your story will give someone else some sanity. Thanks again! I'll let you know when it's posted. Probably sometime next week. Keep praying and believe it or not learning – my best lessons and my greatest strengths were developed under fire!

  • diana1370

    Thanks for the encouragement. You really want to use my store as a feature? Sure, why not. …and there's plenty more to tell you…. :-) I'm just taking it one day at a time and praying a lot! :-)

  • http://reallybadboss.com denised2

    Wow! And I thought I had it bad! I completely, completely sympathize with the position you're in. We all need to work and especially in this economy, it can be hell to even begin contemplating leaving the boss you have. But I've been there – the sleepless nights, nausea, horrible weekends. Right now, the one piece of advice I could give you is to remember that even in this bad situation, you're just passing through.

    This horrible woman you work for would like you to believe that she's got all the power, and maybe in the office she does, but you own and control your personal life and your emotions. Don't let her make you miss another night's sleep. She's irrational, incompetent, inept and an ass – deep down, she probably knows that and that's why she behaves the way she does.

    I'd like to post your bad boss story as a feature – anonymously of course – to see if we can get some suggestions and feedback from other bad boss sufferers. In the meantime, do your best to enjoy your holiday and begin to have the mindset that when you leave your office, leave it all behind. It's not easy to do and it takes practice, but it is the only way to keep your sanity until you find something else. Thanks so much for sharing your bad boss story and I really wish you the best.

  • diana1370

    I was out of work for over a year so when I was offered a job to work at a non-profit agency an hour away from home, I said, Thank you, and took the job. Little did I know that the female version of Adolph Hitler is alive and well and running the non-profit agency where I had just agreed to work. While this woman was unpleasant at the interview, I just assumed that she was having a bad day or perhaps was stressed. I was mistaken; that is the norm. On my first day in the office, instead of receiving any kind of welcome or introduction from her, she approached me as I was still holding my coat, purse and bag containing personal items like Kleenex and reference books, and said, Meeting in five minutes – I need you to take notes. The receptionist showed me where my office was and I hurredly sat my things down and grabbed a pad and pen. There were about a dozen people in the meeting and she never introduced them to me, so I drew a diagram of the seating and numbered them so I could keep the comments straight of who said what. Finally, when there was a lull in the discussion, I spoke up and asked if, since I was asked to take minutes, I could please have everyone's names. The boss later told me that I was never to interrupt one of her meetings again. Afterwards, she gave me several documents to make revisions on, however, I was not allowed to have access to any documents of my predecessor, so I had to completely re-type all the documents. When I went to my new boss to ask a question, I discovered that she had left the office and had locked her door shut – she does not share her schedule with anyone and no one knew if and when she would return for the day. Another admin assistant introduced herself and showed me around the office and sort of explained what my position would be like. I was also told that I was the fourth secretary my boss had had so far this year. When my boss returned, I told her that I had tried to go to her to ask a question but found out that she was gone but the other admin had been very helpful and answered some questions for me. The boss was livid – “WHY WERE YOU TALKING TO HER??? SHE DOESN'T KNOW ANYTHING – SHE'S JUST A TEMP! SHE IS NOT YOUR BOSS – I AM YOUR BOSS! (repeating) ..SHE IS NOT YOUR BOSS — I AM YOUR BOSS!!!” I reminded her that it was my first day; that she was gone and I didn't know if she would be back and the other admin had actually answered my questions. I was reminded that I was never to go to the other admin again for any reason without express direction. …On Day #2, I handed a document to my boss that I had just completed; she looked it over while I stood and waited for further direction from her. She turned to me and said, “You're a perfectionist, aren't you?”, I replied that I guess I am. With a sinister tone, my new boss told me, “I'm a perfectionist, too. We're going to butt heads and I'm going to win.” I told her, “You can win! You're my boss and I'm just here to help you. Why would we butt heads?” She said, We'll see. I have now been here two months and it is some of the longest two months of my life. I cry on my way to work, I cry on Sundays knowing that I have to go back to that horrible woman on Monday. Although she does not usually raise her voice, her tone is always cynical, sarcastic, accusing, condescending and demeaning. She does not believe in training. Her philosophy is that training is “clerical work” and she's the boss around here and she will NOT do clerical work. While I don't need training for my skills, every office is run differently and some kind of training is needed in order to learn and to be most efficient in being of service to your boss. But my boss does not believe in that. There is an assumption that you should come in on Day 1 and know everything there is to know about the agency and your job as if you've been working there 20 years. Since there is no preparation beforehand and you learn very quickly that any kind of question you have will not be answered, or will be answered in such a belittling way that questions your intelligence or willingness to work that you soon learn it is not worth it to ask questions, if something – even the smallest detail – is done in an “unacceptable manner” as the boss deems, you are called into her office and berated for not getting it right. She is completely disorganized, but if you do anything to try to help her get organized, she accuses you of trying to “manage” her. She once CC'd me on an email to her other “staff” where they were to submit a report to me by noon on a certain day. On the morning that the reports were due, I emailed the staff members that had not turned in their report as a reminder that I needed them by noon that day, and I made the mistake of CC'ing my boss. …I was told that I had overstepped my boundaries and to NEVER email “her” staff again without express direction from her! However, a few weeks later, a similar situation arose when projects were due and when I told her that certain people had not followed up and we were missing documents needed from them, she was furious with me that I had not followed-up on this appropriately. She then (at the end of the day on Friday, when I should have been leaving) demanded that I call the offending parties and tell them that if they did not turn the missing pages in by mid-day Monday, she would file everything “as is”. I left voice messages and followed up with email messages, trying to word everything as politely as I could, while still getting across the message that this was urgent and we needed them ASAP. I was told to CC her on the emails. Once again, I made an attempt to leave for the weekend, and instead was buzzed into my boss's office – again she was outraged – because some of the “offenders” were Board Members to whom she answered, and I was told that I had been rude for seeming to rush them. I was then told that she was going to have to call them to smoothe things over with them and apolgize for my rude behavior, and furthermore, I was to meet with her at 10:00 Monday morning to discuss my failings further. I was literally sick all weekend, throwing up from nerves, but that morning, when I went in to work, I came prepared. I literally wore a wire. I stuffed a tiny tape recorder in my sweater and wore it – I still have the tape – my favorite part is when she is telling me how I am to treat the Board Members with kid gloves because they are people with money and influence, I am simply nodding my head to what she is saying when she snaps – “LET ME FINISH!”, as if I had interrupted her – it's all on the tape! ….There is sooooo much more that I could write here…. not enough time to document it all, but it is unbelievable… By the way, today is New Year's Eve and our office is closed today, but I am here because I was sick yesterday. To be more specific, I was driving in to work and a half hour into my commute, I became extremely dizzy and felt I was going to faint, I panicked and pulled off the road and immediately either went to sleep or passed out, for only about five minutes. I pulled the car into a nearby parking lot and since it was too early for anyone to be at the office yet, I was still feeling a little dazed and extremely sleepy – I closed my eyes and went to sleep again. I called the office and told the receptionist what was going on. I told her that I was going to have my sister come and get me and I was going to go home and lie down and hopefully I would be well enough to come back later in the day. After about 45 minutes, my sister did come and get me and took me home – where there were two phone messages waiting for me, wanting to know when I was coming in. I called and explained that I was going to try to get some rest and I would try to come in later. I lay down and had just gotten to sleep when the phone rang again, my boss had asked a staff member to call me to find out, once again, when I was coming in. I was told to call back in another hour or so. Knowing that I would not be able to get any sleep, I got up, got dressed and told them I was coming in, however, I was very upset and I was told to not come in and that instead I would be expected to work a full day today. I told her that I was not expecting to work on New Year's Eve and I had things that had to be done that day that I would not be able to do if I had to work a full day — and I was told to do them yesterday, since I was not coming in. So, instead of getting any rest, I went out, had my car serviced, returned gift items at the store, and had a meeting with my insurance agent and mortgage company. I got home after dark, completely exhausted. So much for getting any rest. And here I am. Not only is our little non-profit agency closed today, but we are in a large, four-story office building, and mine is the only car in the parking lot – I had to have the security officer unlock the doors for me so I could just get in. I still feel sick, but I am here. The boss is due in in any minute – she is going to give me instructions and then leave.