7 Workers Share Their Experiences with the Most Terrible Managers They’ve Encountered

These stories of workplace absurdity paint a vivid picture of the bizarre and sometimes downright outrageous experiences employees face under their bosses. From incompetent and unethical behavior to outright hostility, these stories illustrate the countless ways bosses can create chaos in the workplace.

In the first story, we see how a small coffee shop struggled to survive after a dedicated employee left due to mistreatment by the boss, and highlights the key role employees can play in the success of a business. Similarly, in the second story, a financial analyst’s job satisfaction is shaken by the manager’s failure to provide proper training and support, leading to unfair termination.

Have you ever thought your workday was straight out of a sitcom? Get ready for these confusing and often frustrating stories about bosses who made their employees question their sanity.

Imagine a coffee shop collapsing without its unsung hero, a wily co-worker weaving a web of deceit, a boss who brags about a pyramid scheme, promotions turning best buds into arch-enemies, writing his own warning letter, deftly confronting s*xism in the workplace, and a boss so outrageous that he hits the emergency room to expose the “lie.”

These stories are not just about work; they’re wild rides through professional pandemonium that show the incredible lengths people will go to make a living.

Comments have been edited for grammar and clarity.

A man busy on his work desk | Source: Unsplash

1. I left and the business fell apart

u/VaultHawk: I was working at a small coffee shop, doing a lot of manager work and making minimum wage, and when I got pink eye from taking care of my nurse, my boss got mad at me. After that, I applied and got a job at Starbucks. His business fell apart without me and closed within four months of my departure.

2. I was played by Dirty

u/madeofstarlight: I was a financial analyst excited about my job, salary, and benefits. I wasn’t rich by any means, but I would make $30,000 to $40,000 a year, which would pay all my bills, leave me some savings, get some accessories for my kid, and get my nails done once a month or go out with friends. I was so happy.

A person holding a pen and documents. | Source: Pexels

My boss had the most personable girl in the department trained. And she did it wrong. I found out the same thing happened to two other people in my department. I had no idea I was wrong until two superiors pulled me aside.

I asked if they could train me instead. I asked for retraining SOPs and asked questions when I had them. I was improving, which the boss asked for. She gave no scale, no percentage. She wrote to me because I had errors after two weeks. But so does everyone else.

One morning I caught the girl who mistrained me going through work I hadn’t corrected or turned in and making copies to give to her boss. I knew right away that I was going to get fired eventually and there was nothing I could do. It was terrible.

She acknowledged the training problem when I was fired and said, “What do you want me to do about it?” Then I let her have it without yelling or anything. My position was filled and vacated five times in four months.

3. The Boss Turned Pyramid

Scheme Promoter

u/MartinB75: There have been so many, but I’ll go with the boss who started selling Amway from his office. He pressured his employees to buy something and implied that people who buy from him and join him in the pyramid will benefit (raises, extra vacation, etc.).

Counting money | Source: Unsplash

He also tried to get the company to buy through his side business. I reported him and when HR asked him if it was true he said:

“Sure! Do you want in?” Bam, out the door.

4. Our friendship froze after the promotion

u/ Matopus: I worked in the kitchen in a retirement home. I was the morning cook and became good friends with the evening cook (before he was promoted). Fast forward two months, our chef retired and he was promoted to head chef.

I was happy for him. Shortly after he was promoted, he became increasingly lazy. I had to stay late during the day to ensure all orders were placed and the rest of the staff had everything they needed for their shift.

Two chefs cooking. | Source: Pexels

It got to the point where he was sitting outside smoking. I found out he slept with the building manager’s daughter. When the building manager tried to discipline him, her daughter intervened, telling her not to bother him if she wanted to continue seeing her grandchildren, and even demanding that he be paid.

So I endured it for a few months. When I told the guy that my partner was pregnant and my son was due in July, he said only one thing. “Oh man, that shouldn’t interfere with my birthday weekend. Fast forward to when my partner went into labor (at 4:30 am)

I called him and told him I wouldn’t be able to make it because my son was going to be born. He called me back at 5:30 and asked if he was born yet, and when I told him no, he asked if I could come over for a few hours while we waited.

He hissed on the phone when I told him no and hung up. The first day back he called me into his office and wrote me the missing shifts. I resigned and luckily got a new job right away.

5. With my boss’s kind permission, I wrote and signed my own warning letter

u/knockinbootz: I worked for a real winner for nine years. She sang my praises in the morning, then kept me for two hours after work to tear me down until I cried, over and over again.

She asked me to call her by her first name and then yelled at me for not using her correct title and last name. She was the epitome of “Dr.

Typing on a computer | Source: Unsplash

Jekyll and Mr. Hyde.” She was a real doctor. I was behind on my submissions, so she dictated a threatening letter to me, made me write it, and then signed it.

6. She was friendly to others and mean to me

u/sowhatsoplenty: I got a job bartending at a restaurant a few years ago. I started my first day and met a new guy who was also accepted. I got there and they sent me upstairs to work as a waitress.

I had never served before; I signed up to be a bartender. The new guy had never worked behind the bar and had experience waiting but was told to go behind the bar.

There were two managers; the one who hired me wasn’t there, so I asked the other one. She told me that the girls worked as waitresses and the boys as bartenders.

I was a little annoyed but thought the other manager would fix it when he was there (he wasn’t)! Anyway, I learned that waitressing is not for me.

I was terrible at it! The manager was so frustrated with me that I was even more upset and worse at my job because she was constantly yelling over my shoulder.

Making a drink | Source: Unsplash

Meanwhile, the guy at the bar who had never poured a pint before was left alone, making mistakes and she was yelling at him too.

One night he was alone and a group came and asked for a mojito. He hadn’t been taught how to make them and he had no instructions on how to drink, so I jumped on the bar and helped him.

As I was helping him, the manager noticed me behind the bar, lost the plot, and started yelling at me in front of everyone; it was humiliating.

A woman at a bar | Source: Unsplash

What was worse was that everyone else who worked there loved her and she invited everyone to parties in front of me and was nice to everyone. I was fired by a second manager whom I never met because of feedback from a female manager.

7. My boss is a monster!

u/anonymous: I was 5 months pregnant and felt terrible pain in my stomach. I drove myself to the emergency room. My boss didn’t believe me and said I was faking it. I told him I would bring a doctor’s note.

The doctor examined me and left, then said:

“Madam, I know this may be alarming, but there is no need to call your father here…”

“But my father died a year ago…” I said.

A woman in a hospital | Source: Unsplash

“There’s a man outside right now who claims to be your father and wants your medical records,” the doctor explained.

I was in complete shock, AND THEN A LOUD SCREAM!

The door to the room opened and my boss burst in with a red face yelling, “SHE’S FESTING, SHE’S NOT PREGNANT!!! DOCTOR, CALL 911 NOW!!!” At that moment my husband ran into the room and violently kicked my boss out yelling “YOU WILL PAY FOR THIS!”

After my husband pushed him a few times, he called 911. The officers took the fool to the station. Then it turns out he was keeping fraudulent accounts at work. As a result, my boss lost his job and was forced to leave the country. Karma in action.

These anecdotes reveal the often confusing and frustrating experiences employees endure at the hands of their bosses, turning their workdays into sitcom-like scenarios. From bosses engaging in unethical behavior to displays of utter incompetence, these stories show the challenges individuals face in the workplace. Despite the absurdity and difficulty of these situations, the employees featured in these stories demonstrate resilience and determination to navigate the professional chaos. Their stories serve as reminders of the importance of advocating for fair treatment and standing up against injustice, even in the face of adversity.

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