ask a boss

‘My Boss Is Insecure and Petty!’

Photo: The Cut

Dear Boss,

For the most part, I love my job and my co-workers about as much as anyone can. I even enjoy working for my current boss. There is one problem, however: she’s really cliquey and kind of a jerk.

Our company is very small, so most of my co-workers are part of my boss’ “inner circle,” myself included. But she’s really petty and mean about people who aren’t. Once you do something that displeases her, it becomes fuel for her to attack literally everything about you. I’ve seen her look up people’s social media profiles (in our open office) so she can publicly and loudly ridicule the appearances of employees who quit so long ago that the rest of us don’t know or care who they are. She’s made fun of people’s weight, teeth, noses, autism, age, disabilities, accents, and all sorts of things they have no control over. (Never mind the fact that she considers herself “woke” and “socially aware.”) 

My boss is very insecure herself, so perhaps she’s attacking other people to try and draw attention away from what she perceives as her own flaws. Regardless, it bothers me. She also tends to hire people with similar attitudes, so my co-workers often join in on her pettiness. I feel very uncomfortable about these conversations, but I’m not sure what to say. My boss has previously responded to push-back by making peoples’ jobs more difficult. She’s denied holiday requests, travel opportunities, or anything else that she can. But this only happens when the disagreement is personal. She doesn’t lash out if there’s a disagreement over how a project should be completed, for instance — just if we don’t humor her personal opinions about people.

Other than this one thing, we all get along really well and I don’t intend to quit my job any time soon. But is there a way to professionally handle situations like this? Or should I just smile and tune her out while she rants about some random ex-employee’s weird dimples?

Oooh, your boss is a real jerk.

I know you know this … but do you really know it, at a gut level? It’s an interesting cognitive dissonance to read that you get along well and generally like working for your boss but she’s also a terrible person.

And that’s not a criticism of you! It’s possible to get along with jerk bosses and even mostly enjoy working for them, as long as their jerkiness isn’t centered on you. Jerks can have redeeming qualities! Who knows, maybe she’s awesome at giving you professional feedback and advocating for raises and providing flexibility when you need it. It’s okay to set your own priorities about what you want from a boss, and she can give you things that are important to your professional growth and overall quality of life at work.

But wow, she’s also an awful person. And it’s hard to imagine that someone who likes looking up former employees in order to ridicule their accents or disabilities is someone you can rely on to be a solid professional advocate for you. At some point you’re going to do something that displeases her, or just have a hairstyle she dislikes, and then you’re going to become her target. Maybe that will happen after you’ve left this job but when you’re relying on her for professional references and job leads. Or maybe it will happen while you’re still there, at which point it sounds like your quality of life will plummet. It’s a precarious situation to be in.

And even if she never turns on you, you still can’t trust her, given what you know about her. And that’s a big problem when she’s in charge of your work evaluations, salary reviews, and overall advancement.

None of this means you need to start job searching tomorrow — most people don’t have the luxury of leaving every job where they have a crappy manager — but at a minimum it means you should be careful not to start normalizing her behavior. When you work in a toxic environment, it’s easy to lose track of what is and isn’t normal, what is and isn’t okay, and how not-okay something is … and it can make it harder to recognize when things reach a point you truly shouldn’t tolerate.

Only you can decide if and when you’re at that point. It doesn’t sound like you’re there now, but at some point you will be — and when you start thinking you are, don’t second-guess yourself.

But until that happens, how do you deal with your boss when she unleashes a rude tirade about someone? If she didn’t have a habit of lashing out at people who disagree with her, I’d suggest that you try responding with something positive about the person she’s badmouthing, like “Huh, I like Jane! I’ve always found her really easy to work with.” Or, “I’m surprised to hear that! She’s always been kind to me.” Sometimes that kind of response will nudge the other person into realizing they’re out of line, or will at least make them decide you’re not a satisfactory audience for their rant.

But your boss is punitive! She turns her ire on people who disagree with her on exactly this kind of thing. If she didn’t have power over you, I’d say so be it — let her dislike you. But because she’s shown she’ll start denying time off (!) and otherwise punishing you professionally, you don’t have a lot of options here. I’d love to tell you to push back and stand up for people who don’t deserve her abuse, but it sounds like you’d pay a high professional price for doing that.

Sometimes in a situation like this, you can get away with cultivating a reputation for being so universally kind to everyone that your boss won’t take it personally when you don’t agree with her criticism of others — because she figures you’re just the office Pollyanna who can’t bear to find fault with anyone. But even that sounds risky with her, and it’s probably a strategy you would have needed to have started earlier.

Your only workable strategy may be to tune her out as much as possible and make non-committal noises when called upon to react (followed by quick subject changes). Just don’t let yourself be lulled into thinking you can trust her. It’s not ideal, but that’s probably as good as it gets with a boss like this one.

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 Her advice column appears here every Tuesday.

‘My Boss Is Insecure and Petty!’