my terrible boss

He Showed Me a Dick Pic and Got Promoted

Illustration: Miranda Dempster

Everyone has had a terrible, horrible, no good, very bad boss at least once in their lives. In the bimonthly My Terrible Boss series, people vent about theirs.

When I interviewed with Sean* for a job at an online university, I had just moved across the country and I was desperate for a job. He was really charismatic and he made his work sound really important, so I accepted immediately when he offered me the gig.

When I started working with him, I learned that he made everyone feel like they were his favorite. I thought he just really liked me because I was one of the only younger people, and we were roughly the same age (28).

About a month in, he started asking me a lot of questions about my personal life and telling me about his. He had three kids, he was married. He always talked about his wife; she was either a monster or he was totally misrepresenting her. He said she didn’t wear a wedding ring to work. He told me that she was always pushing him to work harder, even though he made all the money. I was trying to be friendly and sympathetic to a point but I also didn’t want to be friends with him. It was hard because he was my boss and I wanted him to like me. I tried to laugh when it seemed appropriate, but I stopped initiating conversations with him.

Right around the time that Caitlyn Jenner came out as transgender, I was walking by his desk one day and he called me in, apropos of nothing, and said, “Oh, you’ll think this is funny, my brother sent me this picture.” I looked at this phone screen and there was a picture of a penis stuffed up behind butt cheeks in a pair of underwear with “The backside of Vanity Fair” written over it. He looked up at me waiting for my response. I didn’t even know what to say. I thought it was really offensive. I think I said something like, “Oh, I’m not sure that’s my humor. I’m not sure I get that.” I could tell he began to feel nervous then.

I went to lunch with the other people I worked with that day, and one of the people I recounted the story to was the director of academic support, who reported it to HR. Then HR called me in and asked me to tell the full story. I really didn’t want to because I was worried about what would happen to me and my job. I was really afraid that he’d retaliate in some way. But it was clear that HR wasn’t very worried about me or what I wanted.

They asked me a lot of questions about my relationship with Sean — whether I had given him any indication that we were friends, whether I had flirted with him, whether we hung out outside of work. I still have no idea why any of that was relevant. Why would any of what he had done be my fault? They asked me if I wanted an apology from him. I didn’t want an apology, I just didn’t want to talk about it ever again.

At one point, the HR woman said, “I know Sean and I know him to be a good person. This was just a lapse of judgment, he was just trying to make a joke.” Later that afternoon, HR sent me an email saying, “Sean’s really sorry, he understands why what he did was wrong, he just wants to make sure you accept his apology.” I didn’t really say much except, “Thanks for letting me know.”

Within two weeks, he was promoted. It was so quick that I thought there was no way it wasn’t related to the dick-pic incident. When he got promoted, he called us into a conference room to tell us. I didn’t say anything. He was nodding really faux-humbly. I was trying to calculate how likely it was that he was given this promotion because of something great he’d done or if it was a way to move him after this HR complaint.

They also gave me a small promotion immediately after, too. I thought part of it probably was to make me feel good and make me happy and make me stay. Another person that I reported to thought that the whole thing was really shitty. When we went down to HR, she said, “Watch, he’ll just be promoted.” I thought that was something that only happened on Mad Men.

Not long after I gave my notice, Sean had said something to me when I ran into him on campus, “Can we go to lunch before you leave?” I just kept walking. Every once and awhile, he’s recommended to me on social media. I just close the box.

*All names and signifying details have been changed.

Have a terrible boss story you want to get off your chest? Send an email to work@nymag.com and tell us about it.

My Terrible Boss Showed Me a Dick Pic and Got Promoted