14 Real-Life Bosses Whose Antics Could Inspire the Juiciest Office Drama

Many people have encountered challenging bosses at some point, and the stories of their outrageous behavior never seem to end. Whether you’ve lived through something similar or just love a good story, these accounts show just how wild the professional world can get.

• I had to stay late at work to finish some reports. The office was eerily quiet, and I thought I was alone until I noticed my boss sneaking out of his office. He didn’t seem to notice me and headed straight to the office kitchen, looking around like he was up to something. Curious, I peeked in to see him frantically waving a towel at the microwave, where smoke was pouring out. He’d tried to reheat something but forgot to take the metal spoon out. The next morning, he blamed the entire mess on “poor maintenance” and sent out a memo banning personal food in the kitchen.

• I accidentally scraped a car in the parking lot. My boss came sprinting out of the building, screaming, “Who hit my car?!” Embarrassed, I admitted it was me and said I’d cover the repairs. Instead of calming down, he launched into a full-blown lecture about responsibility.
  That’s when my coworker walked by and said, “Boss, isn’t this the company car you scratched last week?” My boss turned beet red, muttered something under his nose, and stormed back inside.

• That morning I spilled coffee on my shirt, the kids were slow getting ready, and traffic was a nightmare. I arrived at work just five minutes late, only to be immediately called into my boss’s office. “Why were you late today?” he asked. I explained about dropping off my kids and traffic, but he cut me off, pointing to a photo of his family on his desk.
  “I also have kids, but I’m never late,” he said. I apologized and went back to my desk, but here’s the kicker: the next morning, he didn’t show up until nearly 10 a.m. I overheard him joking with a coworker about how he “had to swing by the gym and grab a smoothie.” It took all my willpower not to laugh out loud.

• I worked for a small independent company, running the little office doing admin, accounting, etc. I hated the boss. He decided to plant a hidden camera disguised as a movement sensor, perfectly placed to watch me. He told me off for doing a crossword while he was out of the office; I had to snoop around, find it, and quit. © Unknown author / Reddit

• The vice president told me I was being disrespectful during a conversation. I asked how, and she told me that I “knew what I was doing.” I asked again, stating that I had asked because I didn’t actually know, and she replied, “I know what you’re doing, and I don’t have time for this.”
  You’re the vice president, not a 15-year-old angry at her boyfriend. © thatskyguy / Reddit

• I had a boss who refused to let me take an “unplanned vacation” to see my grandma on her deathbed. I quit on the spot. It was strange because up until that incident, she was cool and laid back. But when I asked for the weekend off to go visit my dying grandmother, she snapped and lectured me about how I needed to “plan” my “vacation” better. © ostentia / Reddit

• My boss routinely called me in the middle of the night (11 pm–3 am) to complain about things that could wait until work hours. She would also call in the middle of my evening workouts to tell me to get to my computer and do some more work instead. She would do this on weekends in the middle of dates with my fiancé too. © allonsy90 / Reddit

• I’m a personal assistant and I have worked for some very wealthy and insane people. One of my bosses would tell me every day about the new jewelry and sports cars he was buying his wife. Every day she’d get a gift that cost over $50k!
  He spent more on her daily than I would make working for him in one year. She wouldn’t even look at me or even speak to me unless she had no choice. She would just make hand gestures, or the maid would “translate” her glares to me. © TheLifeofDime / Reddit

• My mom got yelled at by the president of the company for coming back 2 minutes late from lunch. She was pregnant with me at the time. © darth_stroyer / Reddit

• At my last job at a marketing company, our president and owner went on an hour-long tirade to a client, basically calling them "stupid' and "ungrateful". It started because the client, a dentist, presented my boss with some ideas that came from her receptionist.
  They were just the standard advertising suggestions (bench signs, radio ads) that the layperson would know, but nothing so bad that someone deserves to get ridiculed over. © bucaqe / Reddit

• I once worked for a small nonprofit with a terrible executive director. She enjoyed pitting all the senior staff against one another by making up stories about things people had said, promising three people the same promotion, and generally orchestrating power plays.
  Staff turnover, as you might imagine, was super rapid (and not just among the senior staff), but the board of directors never caught on that anything was amiss because the rotation policy was built in such a way that board members rotated off every two years. The whole experience was hideous and nearly drove me out of the nonprofit field. © justaskosh / Reddit

• I said "yep" instead of "yes". She then told me that was inappropriate and that she hated it when her daughter would do the same thing.
  I have 13 years of experience in my field, and a degree in computer science, and have never been anything but polite to you. I hate that woman. I obviously don't work for her anymore. © Unknown author / Reddit

• My supervisor was maybe a couple of years older than me, and for the six months I worked there, never bothered to set me up with my computer. I'd work in the mornings, and she tended to show up around lunchtime, so she told me I could use hers, which was pretty annoying in and of itself.
  But more often than not she'd come in about an hour before I was scheduled to leave, and stand over me, eating her lunch, as I worked at her desk. I'd say things like, "Oh, I'll go find somewhere else to work," and she'd say, "No, no, you're fine." And continued to stand over me as I sat at her desk. © retrouvailles26 / Reddit

• I worked for this guy at an ice cream store. He kept cutting my hours for arbitrary reasons, so I got another job and put in my two weeks' notice. Halfway through my two weeks' notice, I got the flu and tried to call in. He told me if I didn't show up, I would be fired.
  So I showed up, and he told me I wasn't being "cheerful enough" for the customers. So I looked at him, said nothing, grabbed my bag, and walked out the door.
  At this point, he followed me and threatened to call my new job and tell them I was a terrible employee. I called his bluff and then called my new job to give them a heads-up. They said, "We don't care, you're already hired. Feel better, we'll see you Monday." © invisible_23 / Reddit

Every profession has hidden depths and unexpected details that aren’t immediately apparent. In this article, women share eye-opening revelations about their careers, offering a fresh perspective on the work they do.