Worst Boss Stories -- Ever!

Before you go, we thought you'd like these...
Before you go close icon

We dared to ask and you were brave enough to tell! We received loads of bad boss stories -- some sort of funny, some just plain sad. Here are 15 of our favorites...


Stingy Supervisors

1. I worked for a doctor who was so cheap he wouldn't even buy the office a pack of highlighters. When we needed office supplies he would tell us to call the drug company reps and ask them for supplies. It was humiliating to have to ask a drug rep to go to the store and get us a pack of highlighters. He once wrangled 6 free staplers from a rep when we didn't even need staplers. They just sat on the shelf unused. He also liked the free luncheons they would provide and hounded us to schedule at least one free lunch a week for him. -- Amber F.

2. I was working at a restaurant and the boss also the owner was so cheap he demanded that when we got a drink of water we were told not to throw the cup away because it only had water in it to reuse it for customers. – Cynthia C.


Deceptive Mis-Directors

3. My 1st job out of college, my boss made me do all sorts of personal work for her - Christmas cards, party invitations, etc. She was having a big party in her Park Ave. apartment & invited me. I told her that my then fiance would be in town & would it be ok if he joined us. She said that would be fine. I should have been suspicious when she said how pretty my white blouse & black skirt looked on me & would I please wear it to her party. When we got to her apartment, I asked her what I could do to help & she introduced me to the caterer as the waitress & showed my fiance, an attorney btw, to the bar where he would be working! – Erin

4. On Administrative Professionals' Day (formerly Secretarys Day) all of the support staff got taken out to lunch by their bosses. My boss told me to make sure to save my lunch hour for her because she needed my help with something. I thought maybe just maybe she was going to surprise me by taking me to lunch to celebrate the occasion and thank me for all of my hard work. Even when we pulled up in front of her house I thought she may have fixed a nice lunch at her place. Nope, she just needed me to help her put flea collars on all six of her cats. -- Nancy


Sadistic Superiors

5. I was the assistant to this woman at a manufacturing company. She never spoke in a normal voice - she yelled about everything! She threw a stapler at me once for stapling her papers in the top left corner, as she liked it at the top/center - and she missed my head by an inch! She called me a stupid idiot for clipping a stack of papers with the colored binder clips, as she only liked the black ones. – LuckyStrike101

6. I had a boss who used to stand by the clock. So I, along with all of my co-workers, needed to be at work at 8:00 AM sharp. And he would stand there and watch people file into the office. Now we all would panic because he would also, watch the second hand as it counted down. I dreaded being at the end of the line because as soon as the clock turned to 8:01 AM you were considered late! And if it happened more than a couple of times he would send you home without pay for that day. – Phyllis

7. My ex-"New Boss" was an egotistical, maniacal, idiot with an "Inferiority complex!" We both had the same "first name" yet he never seemed to be able to remember mine! He once forced two of his Managers to take their shoes off and place them on the wrong feet to make a point about having the wrong people in the wrong assignments! He did this in front of Associates, humiliating the Managers and causing them to lose their Associate's respect. – MADDOG

Clueless Commanders

8. My worst boss owned a printing company. He was trying to attract a new client. The client was a catholic seminary. The day before the client visit, my boss hung up crosses all over the company from the front door to the bathrooms. – Karen C

9. When I was working in a photo lab, my boss hired a guy who was COLOR BLIND to do color corrections in photos. After having numerous customers bring their pictures back because they were wrong, I decided to inform my boss about the situation. She told me that I was putting him down to build myself up. – Sharon T.

Anti-Social Administrators

10. My worst boss was actually a really nice guy. Unfortunately he had horrible people skills. There were less than ten people in the company. I was his second in command. But throughout the entire 11 years that we worked together, he never once managed to say my name right. Every chance that I got I would try to introduce myself to others in front of him so that he could hear the correct pronunciation of my name, which is not that difficult. But the next time that he would introduce me, he would always have to sort of mumble my name to them because he wasn't sure how to say it. – Rhonda

11. I was the assistant to the administrative officer of a sponsored research lab at a leading university. You would be having a conversation with her about something and suddenly she would 'snap' and her facial expression would change, she would lock eyes with you, and her voice would drop very low. All of us in the office figured she was simply 'crazy'. Then, once in a meeting, she let it slip that she had learned this technique in obedience class with her dog. She first used it on a professor with whom she had trouble communicating. That she found it to be an effective 'tool' in managing people. – RandomVariable

Heartless Heads

12. When my grandmother died, he forced me to provide him with a copy of her death certificate and proof that she was indeed my grandmother before he would grant me time off to attend her funeral. When my grandfather died a month later, he refused to let me go to the funeral because he said I couldn't pull "that trick" again. – Pam

13. My boss had his 80+ Mother-in-law working for him as his accounts payable employee so that he wouldn't have to just give her money to live on...she had no income! His MIL was in his office upstairs from mine, he calls my name very loudly and I ran up stairs. He was talking to his wife on his cell phone. Without hanging up from his wife he says to me, "Would you mind giving her the Heimlich manuever, she can't breath." He then turns away from us and continues his conversation. I left his employ not long after that when he had me plunge the toilet that his elderly father had stopped up as soon as he got to the office! – Alta G.

LowLife Leaders

14. The worst Boss we have installed microphones (bugs) in our cubicles so he could listen in, when we figure out the hidden microphones we started talking in codes or tune in a small radio and tune it to all talk station this drove him nut's, he took the radio away but we still talk in codes till he got fired for being drunk on the job. (Yeah) – Jimi

15. The worst boss that I ever had was when I was about 21 my brother and I worked for an wealthy owner of many service stations. One day we were reviewing our paycheck stubs an saw large deductions being taken for missing tools and equipment. We approached the owner and asked what they were for. He replied that certain equipment was taken and we were all to share the expense. Being young and needing a job you accepted the result. One night we were working late and saw the owner loading specific equipment into his truck and to our surprise we were billed for that equipment. We then walked of the job site and quit. A few years later we read in the paper of his arrest for tax evasion, theft, etc, etc, etc. – Mike

Bonus: Just Plain Wrong...

The worst boss was this guy who as soon as he started to talk to you he would scratch his crotch. This was made worst by the fact that I worked in the Santa's Workshop. – Belynda P.


Next: 43 Things Actually Said In Job Interviews >>

Read Full Story

From Our Partners