Tell Me Your Worst Boss

Talking about worst bosses, I had ask some of my friends all over the world in different industries and collected some of the stories below. See if you can identify your worst boss’s traits in one of the 8 stories below.

I ought to beat everyone’s hands down when it comes to the worst boss in the world. He didn’t respect any privacy and has no boundaries.

I was his personal assistant not personal slave but he thinks he can call me at all hours and expect me to answer his phone within two rings. If I so much as to ignore his calls on a weekend night (because I was sick in bed), he will have a fit and call everyone and anyone in the office to reach me. And it’s not even important!

He’ll call me up just to find out where is the nearest grocery to his place. Come on, there’s Google right?

  • Beebee, Personal Assistant


My boss hate smiling. For two years that I have worked with her, I have never seen her smile. When you do something that pleased her, she’ll keep her mouth shut and that’s when you know you didn’t screw it up. She’s very verbal with her thoughts and never afraid to let you know what she thinks, even to the big bosses above.

She’s not the worst in my office but working with her can be very stressful. We have to tiptoe around her because she hate noises. Well, on the bright side, she’ll never backstab me because she is never a hypocrite.

  • Lawrence, Subeditor

I’m on my final days to the worst boss cum worst company I ever worked in. I worked in a 24 hour hypermarket as a stocktaker and they really don’t give a thought to our well-being. My boss is the worst.

He’ll suddenly demand that I put in extra hours otherwise my pay will be “delayed”. He loves to add in hours to your shift if he thinks you are disagreeable.

Once I was even working 36 hours back to back! Our lunchtime is supposingly an hour but if you get back later than 45mins, he will yell at you for the rest of the 15mins.

  • Pamela, Stocktaker

My ex-boss is a super flirt. She loves to wear mini shorts, you know those that can’t cover your bum? That’s her favourite, she has them in all colours. Sometimes, she’ll walked into the office wearing a tube or a very low cut blouse.

My office is very small, consist of 5 people working there so it can get uncomfortable when she leaning over your desk to “check” your work. She also expect praises from everyone in the morning. She actually gave a meeting on this topic, on how important it is to be positive in the morning to start the day right. But weird, she never dish out praises to anyone in the office.

Most of times, it is embarrassing to see how she flirts with our clients, making the whole office awkward. One time, I even got caught in between when she tries to hug a client and the client was hiding behind my back!

  • Oliver, Accountant

I don’t have a boss. I have a yeller. He always yell. Even his emails are in CAPS. Everything he wants done should be done like yesterday. The benefit is that the salary is good because nobody will stay on their jobs if the money weren’t.

He is slave driver and he drove a couple of us to tears on a weekly basis. Everything is just not good enough for him. Everything gets thrown out. It is extremely stressful to work in such an environment but we all stayed on..for the money. It’s like working for the devil, you know.

  • Simone, Paralegal


My boss loves to blackmail us into staying back late. Even when my baby is sick, she blackmail me into feeling guilty that I left my team behind to pick up my portion of work when in fact, my team tells me that the work could have been completed the next day, there was no rush.

She loves playing mind games, goading and guilting us all the time. She’ll act as if she is the saint, giving us ample chances to proof our worth when she always steals our work as her own and never credit us. I’m pretty fed up with her.

Thank god, she was replaced with someone else beginning of this summer.

  • Analise, Typist

I love my job. It is very challenging and I have learned so many things but my boss is a difficult one. He is a slacker and expects us to pick up his dirty work. He never goes to meeting and always ask one of us to report what goes into the meetings.

At times, he will screw some projects and dictate us to make it right. Half of the time, I bet he doesn’t even know what he is doing. I have the right mind to allow him to mess up big time without being there to help him but it’ll means the whole department will get fired.

  • Ronald, Tech Support

Scum of all scums! I used to work for someone famous. He is supposed to be generous and kind on his public image but noooo….

He will make you work at all hours and he take pleasure when he know he woke you up in the middle of the night just because he has new ideas on his next project. He never say thank you, not once.

There was one time he made me walk three streets down in the heavy rain to get him his coffee when there is a cafe right below our building. Ended up he didn’t even touch the coffee! I was so mad! Worst part was he never pay us on time. Our salaries are always delayed by a week or two. I gave up after working for six months. Not worth it!

  • Rani, Marketing Assistant


My boss hate anything confrontational. She hates disagreement, debate and discussion. Every time someone disagree with her, her face will turned green and she’ll walked out of the room.

Even during appraisal time, she’ll disappear conveniently for many weeks so another manager covering her duties will have to talk to us about our appraisal (he doesn’t even work in our department!)

She’ll make important decisions affecting our department without asking us or at least, informing us in case, we disagree with the changes. I heard a rumour that someone managed to corner her one day to force a debate on her. What did she do? She fainted! 

  • Shahidid, Quality Assurance Officer 

Have you encounter a bad boss? How is it like for you? Do you have any similar stories to share? Comment down below.

If you enjoy this post, you will love these as well:

Top 10 Worst Jobs in the World

6 Types of Bosses that breaks you

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36 Comments Add yours

  1. hcyip says:

    Great post and very interesting, Kally. Some of these bosses are indeed terrible. That said, a super-flirt boss, a boss who hates confrontations, and a dour but honest boss are the worst these people have had? I wish I could be so lucky. Based on this, I think Singapore/Malaysia working cultures must be better than Taiwan and Hong Kong.

    Liked by 2 people

    1. Kally says:

      Ah.. my stories comes all over the world, not just in Singapore and Malaysia. I know your story and I think yours is one of the worst bosses as well.

      Liked by 1 person

      1. hcyip says:

        OK, my mistake. Yeah, that boss I mentioned was a combination of two or three of the bad bosses in your post.

        Liked by 1 person

        1. Kally says:

          Poor you. I’m so glad that you are away from it all.

          Liked by 1 person

          1. Kally says:

            Ooooo!! I’m popping over to read them now. Thanks for the heads up.

            Liked by 1 person

  2. photosociology says:

    I’m going to tell you my best boss. I no longer work for her but she is one of my best friends.

    She is a leader with strong personal boundaries. She knows who she is, so she has no hidden agenda and allows everyone to be themselves.

    She loves having a diverse team and respects that we all have different assets. Substance misuse was the field we worked in and we sometimes faced violence. If a team member made a decision on how to act and it went wrong she would support them.

    She accepted that we, as trained and skilled workers in our area of expertise meant that we were the experts and not her. She was the expert as a manager.

    Always approachable, despite managing a multi-purpose pound budget and working with so many external stakeholders, and all that that involved.

    When something wasn’t working and change was required she spoke to the five team leaders, explaining what was wrong. Those team leaders would then ask there team to come up with the solution. She made us stakeholders in the development of service provision by doing so.

    She also held us accountable. If we were lacking, had made a mistake, were not capable in an area, or had personal problems out of work, she ensured that we took responsibility for it.

    If there was a disciplinary issue she would hold an initial meeting to explore the difficulty and see if the organisation could support by providing training, or making changes in service provision. If there was a personal problem she would firmly suggest that the person take responsibility for a solution, but she did this kindly and without judgement.

    If someone wasn’t up to the required standard and repeatedly continued to act the same despite her coaching then the disciplinary process could lead to a person losing there job. She always gave the opportunity for change so she was not afraid to sack someone. It was the right thing to do. It was her being accountable for her decisions. Thid was always a last resort. She hated the idea of someone losing their job and the impact it would have upon them. I’ve seen her in tears after doing so.

    As a friend, if I fuck up she will be firm in challenging my behaviour, but she does so in a loving and non judgemental manner. She is amazing

    Liked by 1 person

    1. Kally says:

      Wow… looks like you hit gold when you had her as your boss. I have met people like your friend, she’s a keeper. Those who are like that used to be my bosses and now become my best mentors in life. I’m very fortunate and so are you to have someone so inspiring in our lives.

      Liked by 1 person

      1. photosociology says:

        It’s wonderful, and I feel most grateful

        Liked by 1 person

  3. vicklea says:

    I am a retired teacher and I had a principal who was best friends with a few of my colleagues. They went out for drinks, socialized on the weekends, etc. None of the rest of us could ever do anything right, but these few in her inner circle could do no wrong. Then there was the principal who thought he knew everything and just wanted to be friends with the kids. He made teaching almost impossible because the kids knew that they wouldn’t be in trouble no matter what they did. Finally, there was the principal who announced that there was a big fight in the main hall of the main building and that he was leaving. Police and fire trucks were arriving when I looked out my window and saw this “courageous” leader leaving. I locked my door, calmed my students and continued to teach. Needless to say, this principal never returned to the job.
    Good teachers require good leaders and sometimes they are hard to find.

    Liked by 1 person

    1. Kally says:

      Oh wow! Thank you for sharing your experiences with us! Definitely an eye opener indeed. I never see principals as bosses but I do so now.

      Liked by 1 person

      1. ALL of us has had one, but mine couldn’t compete with these contestants.

        There’s a wiener in there somewhere {OPPS I meant to say “winner.”}

        God Bless,


        Liked by 1 person

        1. Kally says:

          Lol! You made me laugh out loud, Patrick! Thank you for the laugh today.


  4. The Words Kraft says:

    I hear stories of bad bosses ruining careers and lives. Personally, I have been immensely lucky in this frontier. All my bosses so far have been good. Yes, some of them weren’t of much help, but they at least didn’t screw around with subordinates. I think the concept of a good and bad boss is somewhat relative. It’s the situations that compel us to be a good or bad boss. When I have the upper management firing torpedos at me, a natural defense mechanism would be to pressurize my team to perform better. That way, I become a bad boss.


  5. libarah says:

    Thanks for following my blog
    Happy blogging😃

    Liked by 1 person

    1. Kally says:

      Likewise! Welcome to MiddleMe!

      Liked by 1 person

  6. Saania2806 says:

    Thank-you for all the likes 🙂

    Liked by 2 people

    1. Kally says:

      No problem at all 🙂

      Liked by 1 person

      1. Saania2806 says:


        Liked by 1 person

  7. I love this article Kally😘

    Liked by 1 person

    1. Kally says:

      Thank you so much, Judy.


  8. waysideviews says:

    Hi Kally

    Earlier I thought this kind of bosses exist only in India. When I did my MBA from a Malaysian university couple of years ago I came to know that worst bosses are universal. But still I believe America & Europe have better job culture.

    All my life I have worked under autocratic bosses (can’t call them leaders). I was toying with the idea of writing a blog about their behaviour. Need time to make it concise and short since the experience spread over two decades. Imagine the plight when you have to work under a boss who farts frequently and think it is his constitutional right!!!

    Surely I will write one soon since your blog has acted as an inspiration.

    Liked by 1 person

    1. Kally says:

      Thank you so much for your contribution. I won’t say the western world has better job cultures but perhaps different job cultures suits different personalities in life. Lovely that you find my post an inspiration. I would love to read if you have something similar written about this topic. Be sure to let me know!


  9. waysideviews says:

    My comments updated today morning are not seen in the thread now. Is it deleted?

    Liked by 1 person

    1. Kally says:

      Got your comment!


  10. I want to be a boss🙈


  11. equinoxio21 says:

    I had 5 or 6 bosses. All were bad, except for one, a woman. Brilliant.
    So when I realized that good bosses were a minority I set up my own business.
    (And then had executives complain about me. Only a few!) 😉


  12. msw blog says:

    Great stories,but really not the worst if you want to talk worst let’s chat about the micro managers, the sexual harassers, those that public demean you cause they thrive on power tripping..

    Liked by 1 person

    1. Kally says:

      Ah that’s true. There are many creeps out there who doesn’t deserves to be bosses.

      Liked by 1 person

  13. Lauren McConnell says:

    Very interesting :)!

    Liked by 1 person

    1. Kally says:

      Thank you, Lauren! I’m glad that you love this post.


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