Ask a Boss: I Have Two Bosses, and They Hate Each Other!

Dear Boss,

I just left my job to start what I thought was my dream job at a much smaller company. I report to Sandy but have an indirect reporting relationship to Michelle, who also reports to Sandy. Sandy and Michelle are both significantly older than and senior to me, and they hate each other.

For Sandy — my actual manager — it manifests in how she directly treats Michelle. In meetings, she talks to Michelle like Michelle is stupid, and questions her constantly. It’s uncomfortable to watch. (It’s worth noting that Sandy is, in general, kind of an asshole. She’s pretty rude and condescending to everyone — but treats Michelle way worse than the rest of us.)

Working for and with Michelle, though, is worse. Because we both report to Sandy, and I’m the next highest-level person on Sandy’s team, Michelle is trying to make me her confidant as she vents about Sandy. She has even called me twice late at night to complain about her, and then I felt sick and anxious all night. The thing is, she’s not wrong in her complaints about Sandy — Sandy truly can be terrible — but I’m having a hard enough time navigating this weird environment on my own without dwelling on it via 10 p.m. phone calls.

It’s putting me in a terrible position — I don’t want to join in, but I need Michelle’s support on day-to-day projects. She’s sensitive, and the few times I tried to get out of the conversation, it was clear that it hurt her feelings, and she took it out on me in, for example, the time it took for her to approve some of my requests.

The company has no HR. I’m at a loss for what to do — I moved my entire life to a new city for this job, and it is starting to feel like a giant mistake.

Any advice?

Don’t conclude that the job was a giant mistake yet, at least not before you try a few strategies to see if you can make things more bearable. It’s possible that in the end you’ll conclude that this setup is toxic enough that you want to get out, but it sounds premature to conclude that at this point.

It might help to think of this as three separate issues: (1) Sandy is kind of an asshole, and is particularly rude to your colleague/co-boss, (2) you don’t want to be Michelle’s confidant about her frustrations with Sandy (and you especially don’t want her calling you at home to vent), and (3) Michelle reacts unprofessionally when you try to assert perfectly reasonable boundaries.

I’d argue that No. 3 is causing the biggest problem for you here, and that if you solve that, it’ll also take care of No. 2 … leaving you with a rude boss. That’s no picnic, but it shrinks the problem to a size that might be more manageable.

So, what can you do about Michelle’s hurt feelings when you try to put up boundaries with her?

First, to be clear, Michelle is really in the wrong here. Calling someone she semi-supervises late at night to complain about a mutual boss is not okay to do. It’s extra not okay because you presumably haven’t given her any signs of encouragement, so she’s creating awkwardness for you in order to fulfill her own emotional needs. And it’s very, very not okay for her to bristle when you try to set boundaries, and especially not okay for her to then penalize you at work for it. So there’s a lot of Not Okay going on with Michelle.

Sometimes with people like this, you can get more traction if you make your request for boundaries more about you than about them. People often have an easier time accepting that you’re on a personal kick to stay positive this year, or that you have an especially high need to disconnect from work once you leave in the evening, or anything else that’s about you rather than about their own lack of social and professional boundaries. So one option is to say something like this to Michelle: “I’ve realized that I’ve been getting really stressed out when I talk too much about work stuff, and I’ve resolved to keep a positive mind-set and not vent about frustrations so much, especially after hours. So I’m going to try to stay out of the issues you’re having with Sandy. I hope you understand.”

Or you could try the more straightforward approach: “Michelle, I love working with you, but because Sandy is my boss too, I’m in a really awkward position here. I know the two of you have a tough working relationship, and believe me, I sympathize. But because I work for both of you, I have to find a way to stay out of it as much as I can. I’m sorry I can’t be more of a sounding board, but it’s important to me to try to have good relationships with both of you.”

Also, on a more practical level: Stop answering her late-night calls. If she continues to call you at home, it’s perfectly plausible that you were sleeping or otherwise occupied when her call came in.

Now, will this guarantee that Michelle’s feelings won’t be hurt and that she won’t take it out on you at work? Maybe, maybe not. But you’ll have said something entirely reasonable in an entirely kind way, and if you ignore her weirdness and continue to be cheerful and friendly to her, it’s likely that it’ll pass pretty quickly. If it doesn’t and if it’s impacting your work, that’s a big deal, and at that point you’d need to address it head-on, either with Michelle or possibly even with Sandy … but it’s more likely than not that she’ll pull it together, especially if you make a point of continuing to be warm and friendly. (In fact, in the week after your boundary-setting conversation, you might make a particular point of saying something admiring to her about work she did that you genuinely think is good or asking for advice on something she has expertise in. That’s not to suck up, exactly — well, it’s a little bit to suck up — but it’s more to nudge her back to normalcy with you again.)

So. Now we hopefully have you in a situation where Michelle is no longer venting to you, but where you’re still having to watch Sandy condescending to Michelle. And that sucks — it’s not pleasant to work in an environment where people are talked down to and otherwise poorly treated. However, if there’s a silver lining to Sandy being kind of a jerk in general, it might be that everyone there presumably knows that’s her way, and takes what she says with a hefty dose of eye-rolling.

At that point, it really comes down to what your tolerance for that kind of behavior is. Different people have different tolerances for that. Some people are great at working with difficult bosses like Sandy and have cracked the code for getting along with them; others will forever be miserable in that setup. But I think you’ll have more clarity and be better able to figure out what you can and can’t live with if you get yourself un-stuck from the middle of Michelle and Sandy’s relationship.

You might also lean on your other co-workers for some insight. Do you have a co-worker who seems levelheaded and whose opinion you respect? If so, it could be worth taking that person to lunch and seeing what they can tell you about what’s going on there. You might learn that things are coming to a head with Sandy and Michelle because of some specific event, or that they’ve been like this for years, or that Sandy talks like a jerk but is also a really good mentor in some areas, or that Sandy plans to retire in a year and everyone is waiting it out, or that there are no redeeming qualities to the situation and everyone is trying desperately to leave. Who knows what you’ll hear — but whatever it is, it will give you more data to factor in as you think about what you want to do.

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