terrible bosses

‘My Boss Texts Pictures of Strippers to My Co-workers’

Photo-Illustration: Marcus Peabody/Getty Images

What makes a boss truly terrible — and how should you deal with it? Advice columnist Alison Green addresses the stories of your worst bosses ever, as part of a weeklong series about what makes a bad boss, and why we’re so tortured by them.

Dear Boss,

The guys in my office circulated pictures of strippers on their cell phones. I was older than most of them by a good 20, 25 years. My boss’s dad helped him carve out some business, he brought his friends over, his wife worked there doing payroll. He was a millennial, and ran the office with his dad’s wallet and a college kid’s mind-set.

My cubicle was next to the main office so I heard everything. The guys spoke to each other like they were in the club. With the stripper pictures, I was standing right there and I saw everything. They weren’t trying to hide it. It was almost like they dared anyone to tell his wife, you know? It was showing off. They didn’t just share pictures, they’d also brag about what they did and where. Not in graphic detail but it would be like, “Oh, you know, we were hanging out last night and there were beautiful girls, blah blah.” It was like working in a frat house.

I was the only brown person there but I think it was more of a sexist thing … I can’t say because I was the only minority, but I never got attacked for being brown. It was just very sexist. And knowing the wife complicated things. It was like, Oh my god. Does she know that they are such douchebags behind her back? My next-door cubicle mate, she was like, “Yeah, did you see all that?” I felt really bad. But then again you gotta say that she knows what she got into, the way he acts, you know …

The law does give you some protection in this situation — although of course sometimes you might calculate that you don’t want to go that route. But it’s important to know that this was sexual harassment and it’s illegal under federal law. Often people think sexual harassment is just about comments or behavior directed specifically to you as an individual, but it also covers situations where unwelcome sexual comments or jokes are pervasive in your work environment.

In theory, this was something that you could report to your employer and they’d be required by law to investigate and put a stop to it. In reality, not every employer handles this well — and while retaliating against an employee for making a good-faith complaint of sexual harassment is also illegal, in practice some forms of retaliation can be subtle and hard to prove. Those factors mean that a lot of women end up staying silent when they’re subjected to this kind of thing, or just moving on to another job. It can be a really tough calculation to make.

Dear Boss,

One of my close family members had passed away, and I went into work that day not feeling very good. I told a couple of folks what happened, a couple of them helped me so I wouldn’t lose step with clients but also make them understand that I’m not going to be available for a little bit. And then my manager pulls me in and starts very friendly, “Are you feeling okay? How are you doing? I’m so sorry that this happened to you. Tragic loss.” I’m like, “Yeah, I’m gonna head home. We’re going to do things over the weekend and I’m just not feeling all that good and I think I’m going to take two or three bereavement days.” And my manager then says, “Interesting. Two or three?” And I’m like, “The company gives them so I think I might take them.” He says, “I’m worried about your momentum. I think we can probably swing one but I’m worried about more. Can you minimize? Can you get that down to one?” 

I was fairly new at the job and worried about making a bad impression. I was like, “Yeah, sure?” So I called my mom and I was like, here’s the situation. We actually moved the funeral to Sunday so I could attend. Then I had to go back to work on Monday, so I missed the burial because they couldn’t do the burial on a Sunday. When I told colleagues what had happened, they were like, “Uh, I would have told this person to go fuck themselves.” I was just not in that space.

He was worried about your momentum because you were going to take two or three days off when a family member died? He’s an ass.

That said, ideally in this situation you would have pushed back and said, “I do need to take the time. I’m going to take the three bereavement days the company provides.” Or, if you didn’t think to do it in the moment, it would have been fine to send an email later saying you realized that you’d need the full three days so you could attend the burial. Your boss wasn’t saying you couldn’t do it; he was pushing (really inappropriately), but if you’d pushed back, he likely would have okayed the days. (In fact, he probably wouldn’t have had a choice since it was company policy.) But it can be hard to know how to navigate that when you’re in the middle of a crisis — and he was a jerk regardless.

Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email askaboss@nymag.com. Her advice column appears here every Tuesday.

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‘My Boss Texts Pictures of Strippers to My Co-workers’