The 11 Worst Boss Stories We’ve Ever Heard

“So I was home from college for the summer and agreed to work for my dad at his insurance agency. I didn’t have a car, so he agreed to carpool with me. He would go to the gym every morning, then swing by home to pick me up.

“One night, he and I got into a big argument (I think over politics?), and we both stormed off to bed. The next morning, I got ready for work, prepping myself for an awful commute. But he never showed up. When I texted him, he responded that he couldn’t let me come into work because it reflected poorly on his business having an employee who couldn’t keep their room clean (there were literally two pairs of shoes on my floor). I should consider myself suspended without pay until such a time that I could clean my room to his satisfaction.

“I ended up thoroughly enjoying a week off of work (during which time I did zero cleaning) until finally my mom explained that if I didn’t have a job, my dad would be paying for 100% of my living expenses. Also he couldn’t actually suspend an employee because their room wasn’t clean or something, I dunno.”

“One day, after work, I was heading to the gym in the office I worked. When I walked into the locker room, the CEO of the company was standing there naked, dripping wet, and making a call on his cell phone. It was a pretty small locker room and there wasn’t really anywhere I could go to give him any space or minimize the awkwardness. His call went to voicemail, and he left an angry message for the head of facilities, telling him that there were no clean towels in the locker room. I offered to go into the gym and get him a towel. The only towels in the gym were small hand towels, so I grabbed a few and took them back to him. He wasn’t very grateful, though. He was just angry that I didn’t find a full-sized towel.”

“I emailed my boss, notifying them I was in the emergency room and wouldn’t be able to come into work for what I thought was an obvious reason. My boss replied, asking me what was on my to-do list for the day and if I could send them the projects I was working on. I begrudgingly complied. They followed up, asking for more information with additional questions—all while I was in the ER.”

“My boss was an ex-con who was the least honest person I’ve ever met in my whole life. He was also in the list of top ten dumbest humans ever to live. His favorite activity was sending me and my SEO coworker outdated/wrong/black-hat SEO ‘tips’ that, if we had followed, would have gotten our sites penalized pretty effectively.

“He was particularly bad at managing the company we worked for, which he was the CEO of. By consistently overpaying what was basically a mafia of account managers and by underpaying writers, devs, SEOs, etc., he ensured that there was a race to the bottom of talent. People who were any good left for a better, less toxic work environment. People who were fresh out of college or prison stayed because that’s all they could do. (This was 2009. Not the best time to be looking for a job.)

“Something I found out later was that this boss was also scamming our customers by telling them that the sites we ‘sold’ them were actually theirs, although our company retained ownership of the domain. I’m pretty sure this is fraud. When bad decision-making eventually led to the company running out of money, we didn’t find out until our paychecks started bouncing. Instead of being up-front about it, the boss told us all that he’d just secured a round of investors and that we’d be reimbursed on bounced paychecks.

“That was a lie. The office was closed up and all the furniture was sold the next week. There was no official announcement, and some of my coworkers who hadn’t quit already found out when they went to work on Monday and the building was locked up.

“They still owe me about $800 in bounced paychecks. I’m one of the lucky ones, as some were owed more.

“This boss moved immediately to California and couldn’t be found. Pretty sure he was afraid of lawsuits from both his clients, who he scammed on purpose, and his employees, half he scammed on purpose and half because of extreme carelessness.”

“Early in my career, I was the number-two assistant manager at a chain restaurant, working under a new general manager (let’s call him Jim) who had been a stern drill sergeant in the Marines during the Vietnam Conflict. Our previous boss had been quite laid back, and some company rules and regulations were not strictly enforced under his regime. So when Jim arrived, it was a bit like Clint Eastwood taking over the recon platoon in the movie Heartbreak Ridge. Jim was a stickler for enforcing his rules to the letter. But unlike company-wide rules and regulations, Jim’s personal rules weren’t written down anywhere. And under those circumstances, the crew initially made a lot of unintended mistakes while they tried to figure out exactly what Jim required. Unfortunately for us, Jim’s disciplinary solution was immediate termination. We all lived under a reign of terror (of sorts) for months as employee turnover climbed toward 200%. When Jim announced that he was taking a job at another company, I nearly jumped for joy. While I worked for him for only 10 months, I learned a lot about bad management during his tenure, and I think those lessons helped me become a much better leader.”

“At a previous company, our standard management call usually included a handful of sales staff and sometimes operations folks. We had many different facilities, and many people worked from home, so the call was always over a big web conference. On one particular day, I opened up the conference window and saw that there were actually closer to a dozen callers, including a marketing consultant and one of our investors. Our CEO called in with the characteristic chime. And unlike most days, a video window opened, showing his hairy torso in living color. I assume everyone else saw it too, but nobody said anything. There were a few moments of apparent hesitation in people’s voices, but not a word spoken. I feverishly private-messaged him that his webcam was on, but he must not have noticed because he made no effort to cover up. Now, working from home myself sometimes, I understand the inclination to keep it casual, but shirtless is a bit much. This was a comedic moment (and a severe cringe-inducer) that I’ll always take as a cautionary tale. A real case of the emperor wearing no clothes. My takeaway: always wear clothes on a conference call!”

“My first job out of college was a sales job, and I was really terrible at it. However, somehow (WHY?), the vice president of talent and acquisition really loved me and promoted me to the recruiting manager. I had no recruiting experience, and before I knew it, I had to hire 7+ people a week. Hello, revolving door! Anyways, my manager was legit CRAZY. Everyone at the company hated her, and at our company party, she sang love ballads the whole time. I quit that job after three months in total when I realized the CEO was a skeeze. Cheers to terrible companies!”

Back when I was abroad in Scotland, I came across an indie film group. I pitched to them the idea of me scoring their short-length movie, and I was hired to do the job. With experience writing for film and theater under my belt, I explained to them before shooting began what the typical process for a film scorer is. They said that it wasn’t correct and said their way was more efficient. It wasn’t.

“First, they didn’t give me a full copy of the film. Ever tried writing music for a movie you’ve seen only once on a laptop in a dark room? It is not a fun experience. You have to guess and hope the music hits the right moment. But hey, they asked me to write music without looking at the film—then criticized me for not hitting the dramatic points. My fault, I guess. To make things worse, there were three directors working on this film and each had a different taste in music. Trying to combine solo acoustic piano, industrial synthwave techno, and Wagnerian opera themes into a 10-minute short was not only difficult but completely impossible in terms of satisfying any one out of the three directors.

“During all the feedback sessions, I received interesting critiques. I can easily take negative criticism, but telling me that the ‘correct way’ to write for a piano is to just keep to an octave (for you non-music folk out there, basically think a measly eight-note span) is beyond absurd.

“If you thought that was weird, try appeasing demands to write music for a 45-second scene as ‘a battle between acoustic piano and electronic music, where it seems the electronic music at first is winning, but the underdog piano fights back and wins—transitioning into the next scene.’ Funny how after I was fired, the next hired composer was asked to write a single note drone underneath.

“In the end, I’m glad I cut ties with them.”

“One of my first jobs out of college was writing for a local newspaper. My relationship with my editor, a.k.a. my boss, started out great but quickly took a turn for the worst.

“One of the most memorable moments I have of just how screwed up my job was happened after I wrote a story about a book fair the local library put on. (Real compelling news, I know.) The librarians hosted a bunch of games for the children, one of which was a game where they’d try to throw a hula hoop around a bookend.

“After writing the story and submitting it to my editor, I got an email back requesting a certain photo to go with the story.

“But let me back up for a second and explain how my editor sent emails. The subject line would include all of the contents of the email. That’s right, when you opened the email you’d find nothing else inside.

“So my inbox dings and here pops up this email with the subject line: ‘Send me the photo of the hula hoop flying child.’ Word for word. I will never forget my train of thought as I tried to puzzle out just what the heck a ‘hula hoop flying child’ was.

“Eventually I figured it out, but that will always be one memory that never goes away with time.”

“I once got into a disagreement with another female coworker, and when my boss called us both in, he said, ‘I actually just listened to a podcast about how conflict is a common thing when you have multiple female employees working in the same office, so I’m prepared to handle this.’”

“I had a boss who refused to leave his office. He’d lock the door and make himself ‘unavailable.’ While that in itself is definitely irksome, it reached a whole new level when the cleaning crew complained about the bottles of urine he’d leave in his office. So yeah, he really wouldn’t leave for anything . . . even to relieve himself. I still shudder thinking about it.”