13 Bosses Who Treat Boundaries Like Optional Fine Print

Many of us had a boss who pushed the limits—but some take it to a whole new level. In this article, we’ve rounded up 13 jaw-dropping examples of bosses who ignored personal and professional lines like they didn’t even exist. Get ready to be shocked, amused, and maybe a little too relatable.

• I had a boss who refused to let me take an “unplanned vacation” to see my grandma on her deathbed, so I quit on the spot. It was strange because, up until that incident, she had been really cool and laid-back. But when I asked for the weekend off to visit my dying grandmother, she snapped and lectured me about how I needed to “plan” my “vacation” better. © ostentia / Reddit
• I once worked at a company where the CIO (Chief Information Officer) sideswiped a woman’s car as she pulled into a parking space. The woman, who had the car that got hit, got out and stood beside her car to see what damage was done. The CIO got out of her Mercedes and brushed right past the woman without so much as speaking to her—completely ignored her and walked away, even with witnesses.
  The woman who had her car damaged had to go to the HR department, and the company cut her a check for the damages. (The actual business paid for it—not the CIO. She got away scot-free without ever admitting anything or paying anything.) © lets_start_*** / Reddit
• My supervisor at this nonprofit was maybe a couple of years older than me, and for the six months I worked there, she never bothered to set me up with my own 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 then continue to stand over me as I sat at her desk.
  She was also the Director of Marketing, and for about two weeks, she had me walk around the city putting up flyers in various cafés and buildings for this class we were hosting. Two weeks later, she’s frustrated that no one’s signed up. As the Director of Marketing, you should have some sort of better strategy than putting up flyers in coffee shops... © retrouvailles26 / Reddit

• Several years ago, I started a new job and was told the office would undergo a reorganization in the new year, and my position might be moved to a different work group. A month later, we were in the middle of managing a major year-end event that required full coordination across multiple divisions.
  Everything came to a standstill because of one colleague in my office. She hadn’t prepared adequately, and the entire process fell hours behind schedule, leading to significant issues. She then had a meltdown and stormed around the office, yelling at people. Guess who became my new supervisor? © shrimpcreole / Reddit
• I’m in the Navy and have actually had good experiences with my supervisors. Even the one I’m about to talk about isn’t terrible. It’s just that he’s never around—ever. Whenever you need him, he’s not in the office, not in the building, and his car is gone.
  He has all these pet peeves and enforces rules that aren’t really necessary. But the moment you decide to go against his “ways,” sure enough, he suddenly shows up and demands to know why things aren’t being done the way he expects. © Unknown author / Reddit
• I said “yep” instead of “yes,” and she told me that was inappropriate — even mentioned how much she hated it when her daughter did the same. I was taken aback. I have 13 years of experience in my field, a degree in computer science, and have always treated her with respect.
  It was frustrating to be talked down to like that. Honestly, how someone chose to start a family with her is beyond me. Needless to say, I no longer work for her. © Unknown author / Reddit

• I once worked for a small nonprofit with a terrible Executive Director. She thrived on pitting senior staff against one another by making up stories about things people had said, promising the same promotion to three different people, and orchestrating power plays.
  As you might imagine, staff turnover was extremely high—not just among senior staff. But the board of directors never caught on, largely because their rotation policy meant members cycled off every two years. The whole experience was hideous and nearly drove me out of the nonprofit field altogether. © justaskosh / Reddit
• I worked outside in seven-hour shifts with only a 30-minute break. One day, I stepped inside just to get a drink of water, and my manager told me to get back to work. That was the day I quit. © TheSNStang / Reddit
• I worked for a guy at an ice cream shop who kept cutting my hours for arbitrary reasons. So I found another job and put in my two weeks’ notice. Halfway through that notice period, I came down with the flu and tried to call in sick. He told me that if I didn’t show up, I’d be fired.
  So I dragged myself in—and then he told me I wasn’t being “cheerful enough” for the customers.
  I looked at him, said nothing, grabbed my bag, and walked out. He followed me and threatened to call my new job to say I was a terrible employee.
  I called his bluff and gave my new job a heads-up. Their response? “We don’t care—you’re already hired. Feel better. We’ll see you Monday.” © invisible_23 / Reddit

• I started working at a company where, on my first day, the owner was hospitalized for a high-risk pregnancy during her final trimester. I had no real training, no idea what I was doing, and was left to figure everything out on my own. The final straw?
  She had someone install two webcams—one facing me, one facing my screen—along with a mic and speakers hooked up to my computer. I found out during a phone call that the line was open the entire workday, and she was watching me for eight hours straight. Was it to make sure I was working? Doing okay?
  I have no idea. But it was incredibly creepy. I didn’t stick around to find out. I was out of there. © EntropismAtWork / Reddit
• I worked at a glass company a few years back, and the bosses were incredibly cheap. One of the older guys was out on a job when he got a call that his mother was passing, and he needed to come immediately to say goodbye.
  He called the owner to let him know he had to leave and that they’d need to find someone to cover for him. The owner kept him on the phone for half an hour, arguing with him to stay—just because it would be cheaper than canceling the job or finding a replacement. The guy got to the hospital too late.
  And when the owner found out, he showed no remorse whatsoever. I’ve never seen anyone display that level of heartlessness in my life. © astrohallow / Reddit
• I had a boss who made me work the weekend of my friend’s wedding—just to remind me who was in charge. I was the best man, and there was absolutely no reason for me to be there. The rest of my team was off, so I ended up spending most of the weekend just wandering around the plant. © stljeeper / Reddit
• I was on vacation with my family when I noticed my wife talking to a man. I instantly became alert—until I realized it was my boss. As I walked closer, I froze when I heard him say, “Your husband actually begged me for a promotion. Said he couldn’t feed you otherwise.”
  I felt like I’d been punched in the gut. “Excuse me?” I said, stepping between them. He smiled like nothing was wrong, “Just making conversation. Lighten up.”
  But I was fuming. I had never begged for anything—I earned that promotion and was even told I was overqualified. Clearly, he had a very different story in his head.

Toxic leadership isn’t just frustrating—it can take a serious toll on well-being. Hopefully, these examples remind us all of the importance of speaking up, setting clear limits, and knowing when it’s time to walk away. Find more articles here.