The Worst Boss in the World

By Estelle Sobel Erasmus

Bad Bosses

I have had a lot of bad bosses (male and female) in my career, but this one set a new low bar for worst bosses.

He hired me and then hit on me.

When he found out I had a boyfriend, he then asked me if I had any friends to introduce him to who were as nice and attractive as I was.

I told him I’d think about it.

When he ran into me and a friend having dinner, he asked me about that friend and got me to give him her number. He called her a month later and told her that he was dating someone, but would like to hold on to her number should his situation change. (Boy, was she turned off).

Once I got engaged, he asked probing questions about my desire to start a family (I hedged). Then he told me that my job was not really suited for women with children because I would be traveling a lot.

When I sent my ring to the jeweler (to get it fitted to match my wedding ring), he sat me down in his office and asked if there was trouble in paradise. I assured him all was fine. He looked disappointed.


He worried that I was looking for another job. When I had a gynecologist appointment, he had his secretary call and tell me to come back to the office. He thought I had taken too long. I literally was in stirrups when I got the call.

There were whispers that he listened in to our phone calls; that he hacked our computers.

Why did I stay in the job?  I was making good money, and was planning my wedding in Hawaii (so when I got home at 9:00 pm from work, it was only the afternoon in Hawaii). Not sure I could have pulled off the wedding planning any other way.

I got married and he started treating me poorly. Telling me that I shouldn’t bond with the clients (?) and trying to ruin my friendships with my colleagues by interfering. Finally, I reached my limit. I left the job after he cursed at me ( he’d cursed at others but I thought I was immune to his uncouth wrath).

He said, “Estelle, I may not have any power over you in your personal life, but in this office I completely have f-in  power over you.”

I started looking for a job the next day. Two months later I accepted another position and gave my notice.

I heard clients were leaving in droves, because he had a habit of hiring unqualified lower level staff. He started letting people go who made large salaries and kept others who were making low wages (like the administrative assistant who overnight became VP of Client Services, and who went back to secretarial work after she left his employ).

Last I heard he was trying to sell the company.

Nobody was buying.

What’s your story about the worse boss you ever had? 

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45 thoughts on “The Worst Boss in the World”

  1. I once worked for a husband/wife duo that owned a Construction Company. I started out part time just helping around the office but then was offered the Office Manager position. It was great at the beginning. Until I couldn’t see eye to eye with the husband on paying bills on time. He would yell at me about his late fees on the business bills and his personal bills (which I had no control over). I tried explaining that you have to send the payments in a few days early for mail time, but it didn’t matter. He was just looking for someone to take his frustrations/life out on. I finally got fed up with the treatment and called the wife and said I was quitting. She threatened me. Told me that I owed them. For what, I have no idea. I never received my final pay. Which back then was a big deal as I didn’t have any other sources of income. I could’ve turned them in to the Workforce Commission, but that required a teleconference call that I didn’t want to take part in. So glad I left that job.

  2. I have been so lucky, apparently. I’ve mostly had really great bosses – some I even consider mentors.

  3. I have actually been blessed to have great bosses during my career. Sure, they might not have been perfect but I’ve had overall good experiences.

  4. Okay, you totally win! I did have some issues when I became pregnant with my boss but nothing like this. I have to hear more stories. I’ll be reading on. 🙂

  5. He sounds TERRIBLE! I can’t even imagine. My worst was when I was 8 months pregnant and working as a retail manager. I had came into work at 3pm the day before Thanksgiving and was still there at 5am Thanksgiving morning {14 hours later}. I was exhausted and in tears and told my boss I was leaving and he screamed at me. I went to my doctor a few days later and she put me on leave early.

  6. Whoa I hate bad bosses because they make it bad for everyone else. I had one boss who use to steal. I am not a tattle tale until she started to set others up and other people use to get fired because of her that’s when I had to say something. If you steal that’s on you but don’t put it on others.

  7. That IS the worst boss ever story! My worst boss was a rich boy with a propensity for bad decisions and lots of screaming. He had a great product and an awesome staff and he nearly ran the business into the ground. Worst things he ever did? Call me from the toilet with a task to do, 5 minutes after he left the office and yes I do mean a real toilet visit, blech! Made me stay 5 hours late, changing the same commas on his presentation, while his Even More Awful Partner ate the dinner he ordered me, and left me the food I hated. Fun!

  8. Yikes! So glad you were able to change your situation and move on! Thankfully, my bosses have all been pretty darn good. A rarity, I know.

  9. I had a supervisor hit on me once, but he didn’t harass me. He just let me know that he was interested if I was. LOL but boy do I have some stories about BAD bosses – like the one who called in sick 3 times a week because management was allowed to miss up to 3 days a week with pay without needing a doctor’s note.

  10. Oh, what a horrible boss!

    My worst was probably the one who told me that I couldn’t have any bathroom breaks for 6 hours… when I was 9 months pregnant.

  11. My worst boss was one that became friends with some of her staff. In my opinion it is completely inappropriate to have your staff talking about the body shots you were doing while out with them on Saturday night. I’m really supposed to take you seriously?

  12. OMG What a d-bag!! I’ve had bad bosses in my day. I temped as an admin to work my way through college…one boss was so bad that he was being sued by some of the employees, and I was deposed! I actually had to go down and give a deposition on how awful this guy was LOL.

  13. I had a boss who yelled at me for being upset about 9/11… on 9/12. He then yelled at me for not automatically staying later when a coworker called out sick. Bad bosses… grrr.

  14. Had a boss who owned his company and was fond of pointing at the glass door and saying, “See that? That’s myf-in name on the door. You’re not happy? Don’t let it hit you in the ass on the way out.”

    All mail was to be sorted, opened, and reviewed by him before it was distributed to employees. I was screamed at once for not leaving a “have-you-seen-me” flyer in his chair while he was out of town. Also screamed at for not leaving the mail on a Tuesday following Columbus Day.

    No correspondence was to be sent out without his viewing/editing/approving it. I’d get screamed at for allowing employees to take their mail straight to the post office instead of giving it to me to give to him.

    I was supposed to ask the investors if they’d like coffee every single time they came in. Problem was, one of them didn’t drink coffee and asked me to stop asking him. I was nearly fired for following the investor’s wishes.

    His “accountant” bought a bunch of plants for the office. Nobody informed me I would be responsible for them. He comes in and starts screaming at me that he was “too important to have dying plants all over the office” and to get my ass up and get them watered or (see part about door above). A few months later I’m up watering, the phone rings, the other 2 women who are supposed to answer ignore it and he hunts me down to tell me he’s too important to have to answer the phone, he doesn’t pay me to run around watering plants, to stay at my desk and do my job. Whew! Right? Nope. A few months later, he threatened my job again because the plants were dying.

    He went under about 6 months after I left. Much as I like to fantasize that I had been the glue that held the joint together, I was only the receptionist.

  15. Was he married? I have seen that!
    My worst boss told me I was too optimistic and up beat. I was in sales!
    He had issues and after he went on some medications and stopped self medicating he actually thanked me for bringing the car to a complete stop for him to get out, knowing I wanted to push him out of the car!

  16. Ugh, how horrible. One time I had a boss tell me that I “was going to have babies” and that a male counterpart would be better suited to get a promotion. Needless to say I was speechless, humiliated and angered….I wound up going to HR and someone went to sensitivity training….(and I didn’t get the promotion at that time, it took another few years after that!)

  17. I actually had a dreadful female boss. It was a VERY small staff, but whenever she got in a mood, she would berate any of us in front of the rest of us. I would “get” it over reports, etc., being “late” although they had been waiting in her inbox for days. She would make rude comments about our clients to the rest of the staff: fat, stupid, ugly, etc.

    She had actually not started out that way; we suspected she had a secret drinking problem, but… it was a HUGE relief to get out of there.

  18. This is awful! Makes me sick to think someone would be that way. Gross.
    Worst boss… a guy who I felt was scamming the world with his computer software. He did such a good job convincing himself that it was a good product. He became a millionaire based on false promises…

  19. I wonder if there is a “bad boss” instructional? I have a long sad story about the worst boss ever. Maybe someday I’ll write about him. He was my ex’s partner, and although he never sexually harassed me, he was a dick. I once heard him say to my assistant: Wow, you really have a nice ass! This was in the 90’s. Yeah, no. On an up note, whenever he would be a total dick, my dog would poop in his office, as if on cue. Boy did I cry when Duffy the shih tzu passed away, he was my hero.

  20. My worst boss ever was a woman. She would be all nice then turn around and use it against you or sabotage you to the store manager. She would do everything she could to make you look bad even when it was her fault. It got so bad I transferred to a city gas station. She ended up getting fired for stealing. Who steals 5 gallon containers of ice cream?

  21. That’s awful. I once had a boss who told me I had to flirt with our clients to get the best deal. Ugh. That was in the late 70s, and I’d like to think men bosses have come a long way since then, but there’s always the jerk who thinks he can treat women that way.

  22. Oh, Estelle, so sorry you had to endure this. I wish you could have reported him to someone in authority. No one deserves to be treated this unfairly, and being harassed should not be tolerated by anyone in any job. You clearly were young because today you would never put up with such nonsense. Younger women should never, ever tolerate this kind of behavior from any boss. NEVER.

  23. Oh my goodness, that’s terrible! I had a boss who was a little clueless because he’d been the King so long. He’d eat off your plate at a client dinner. He scratched his privates during my review meeting.

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