25 Nightmare Boss Stories You Can Relate To

One assistant was put in charge of constantly covering up the boss’s affairs with two different women. She’d have to go and pick up extravagant gifts and send flowers along with book hotel rooms. He was even known to entertain these women at the office. The wife was never to know.

One employee was called into the boss’s office because he smiled too much. His boss said that he just couldn’t trust anyone who was always happy. The employee just smiled at him and left.

One federal employee had a boss who encouraged him to help steal a computer for his daughter to take to college so he could save the money. When the employee refused, he was fired. Even though the employee filed a complaint and it was later found that the boss was indeed stealing things, he wasn’t fired because they didn’t want to ruin is 25 year career.

One manager kept her team going through all the stress of the job by supplying them with Monster Energy drinks. When one employee politely declined, he was “strongly encouraged” to go get one. Once he did, he left it sitting unopened on his desk. When the manager saw it, he was called into the office and told his “lack of energy was extremely distracting.” He ended up being temporarily fired and rehired for a different department. His boss was fired for illegal stimulant use.

One executive assistant had her boss show up to her wedding to ask her a question only she could answer. He was escorted out by police when he refused to leave. She quit before she left on her honeymoon.

One employee was given permission to work from home 1 day a week. Little did she know, there was a catch. She was reprimanded for stepping away from her computer at home and was told she’d lose her at-home privileges if she didn’t inform the boss when she had to walk the dog or make a cup of tea.

One employee had her boss put their hand inches from her face to silence them…in the middle of a meeting in front of everyone…while answering a question that was addressed to her.

When one employee asked for time off as her grandmother was dying, she was told to stay and finish the day because, “she’s not dead yet, so I don’t have to grant your leave.” She quit immediately.

One manager refused to learn her intern’s name. She didn’t even attempt, and in fact, just called her “intern” whenever she needed to get her attention. She also tried to pressure her to drink at off-site team locations and told in depth stories about her sexual exploits.

One employee recounts working in a busy call center type of environment. They were so busy that management actually had bathroom request buttons installed on employee computers. Anytime someone had to use the bathroom, they had to press the button and hope their request was granted. Many times, it was declined.

During a performance review, one employee was kept from a raise because the boss had an “intangible vibe” that the employee didn’t deserve a raise.

One personal assistant recounts a boss who always asked for his coffee really hot. After it was brought to him, he’d leave it sitting there for an hour, so of course when he finally drank it, it’d be cold. One day, he went over to his personal assistant, said the coffee was like “cat piss” and dumped the coffee directly into the assistant’s inbox!

One employee slipped at work and hurt her ankle. Her boss told her to stop moaning and put her foot up and finish the invoices. Five hours later, the boss finally had someone take her to the ER. Turns out she had broken her ankle!

One employee recounts how, in a fit of rage, his boss picked up a small printer and smashed in on the floor. While this employee left soon after, his co-worker continued to endure abusive language until the boss was finally put on temporary leave.

One woman recounts a time when she was giving a presentation. Her hair was up in a ponytail, and when she turned towards the screen, she must have gotten in the CEO’s way because next thing she knew, he grabbed her by the ponytail to move her head! She quit a week later.

One journalist based in NYC had a boss who’d take her completed stories, publish them as his own, and then yell at her for not turning in enough work.

When one boss needed the attention of her employee, instead of calling her employee’s name, she’d throw things out her office door to get their attention. She’d throw pens, staplers, cups…anything in her reach.

Once an employee got very ill and had to be out of work. The boss was very indignant and called HR saying the employee was faking it to get out of work. After being harassed by HR, it was apparent the employee wasn’t faking it. They finally got the respect they deserved after threatening to hire an attorney.

One police officer ripped his uniform pants while tackling a drug dealer. When he requested a new pair, he received a written reprimand for destroying department equipment. Why? Because the pants he ripped were “summer” pants and it was winter.

This one company held an annual holiday party where the employees would get a holiday bonus. After receiving a “better offer,” for a different party, the boss canceled his own company’s party and kept all the bonuses. All this only 4 days before the party.

Some bosses don’t realize what a job description is. One employee was tasked with mowing the lawn around the office building…in her high heals and dress.

One employee was sent to leave a note about work at the grave of a family member of a grieving employee. She’d been out on bereavement leave for a couple weeks and when she wouldn’t answer her personal phone when the boss would call, he took to writing a list of questions only she could answer and have someone leave it on the grave.

You know when people are super generous and it turns out their generosity was just a way to control you? Back in the 19th century, American engineer George Pullman created an entire town just for employees and their families, complete with stores and schools. While that may sound awesome to some, he also paid people with his special money that could only be used in his stores. When he wasn’t making as much money as he wanted, he cut wages but refused to lower rent.

One employee got called into the boss’s office where she was told she was getting a raise. When she mentioned it to him the next day, he took it back and reminded her that he was drunk every afternoon and anything he said after noon couldn’t be taken seriously.

Chemotherapy isn’t a walk in the park from what I’ve heard, and because chemo and cancer aren’t happy things, this one has to take the cake. This one employee was in the middle of chemotherapy sessions when her boss would repeatedly barge in on her chemo treatments to chat about work.

Nightmare bosses don’t hold a candle to these 25 Two-Sentence Horror Stories That Are Actually Scary