The Worst Boss I Ever Had: 11 True Stories That'll Make You Cringe

I once had a boss who knew that I needed to go to physical therapy sessions due to an accident. He told me that wouldn’t be a problem. Yet, when one of those sessions was at the end of the day on Friday—he had plans too. So in front of a very senior leader at the company and a client, he said that I’d take the lead on it, then took off.

My first job out of college was in sales, but it operated much more like a call center (mistake number one). As a result of the high volume of incoming calls, every rep was required to be on the phone and at their desk at all times. That meant we had a ‘bathroom request’ button on our computers. Any time you had to use the restroom you’d click the button, cross your fingers (or legs!), and hope for the best. The requests got kicked up to my not-so-great manager and nine times out of 10 denied immediately.

At my first job, my manager was new to the game too and overbearing (i.e., did things herself rather than empower her employees). We sat at a star-shaped table, so every time I looked up I made awkward eye contact with her. Initially, I liked the micromanagement since I had no clue how to do my job. After finally working up the confidence to lead a call, I remember working to lighten the mood by saying a joke to the client. I watched as my manager (in my direct line of sight) immediately made a painful over-dramatic cringe in response. My stomach dropped, and so did my excitement for the role.

I once had a boss who, in weekly team meetings, would treat one person like a hero and another person like a total loser who wasn’t doing anything right and was going to bring the team or even the whole business down. We’re talking full-on hazing in a group setting. You never knew who was going to be the victim, so we all dreaded the meeting. Once you realized you weren’t going to be picked on that week, you could breathe a sigh of relief for a second, but then you felt just horrible for the person who was the victim (and you felt really guilty if you were the praised hero that week). Not surprisingly, there wasn’t a lot of substance behind why an individual was being praised or hazed so much; it was just a management technique.

When I was an intern at a PR firm, my manager would make me run her personal errands (pick up dry cleaning, ship things, drive her and her friends to SXSW events, etc.). She would get my attention by calling me ‘Intern.’ At more than one off-site team building event where alcohol was served, she not only pressured me to drink and made fun of me when I didn’t give in, but she also told me, at length, about her recent sexual exploits with a married real estate agent. Needless to say, when they asked me to stay on full-time, I politely declined.

I once had a boss who decided that, despite very strong performance, they didn’t like someone on our team and wanted to see them gone. They didn’t have the ability to fire them, but looped the employee out of emails and conversations, talked poorly about them behind their back, and disregarded any good performance. Not only is that unethical (and possibly illegal), but it also made actually getting our team’s work done way, way harder.

I once had a boss who, while I was replying to a question addressed to me by their boss in a meeting (with whom I had worked before and had developed rapport), actually put their hand less than an inch in front of my face to silence me so that they could answer instead.

Early on in my career, I worked at a company that would rotate employees around to different projects with different managers. One of my bosses during this time was The Worst: He’d interrupt me in the middle of focused work on a model to ask intensely, ‘How are things going?’—and then, if I was at all slow in answering something (because my concentration had just been 318 rows deep in Excel), he’d jump on me with questions like: ‘You seem nervous. Is there something wrong?’ or ‘Why did you choose that exact word there? Were you implying something?’ I later found out he was a former interrogator and it he was probably using the same hard-nosed skills on me. I couldn’t have been more relieved when my rotation ended!

I once had a boss who nearly always multi-tasked in meetings by being on her phone and present in the meeting. In both 1:1’s and in group settings she would shift her attention constantly from the speaker to her phone—back and forth, back and forth like this for the entire time. At first, I just thought she was extremely busy, and it was the only way for her to get everything done—until one day, I caught her doing crossword puzzles on her phone while doing a check-in with me.

Once after finding out that I was a lesbian, my older boss (who was a woman) asked me, ‘Would you ever...you know…with me if I was a lesbian? You know I’m not, I’m happily married, but if I was, would you?’ Being at work with her every day made working there miserable.

Although I’d gotten approval to work from home one day a week (my boss WFH three days a week!), if I took my eyes off of my computer screen (we used Gchat to communicate throughout the day) for three minutes, my manager harangued me. She told me I’d lose my remote privileges unless I started letting her know when I was getting up to take the dog outside, make a cup of tea—or use the bathroom.