my boss’s constant self-deprecation and oversharing make me uncomfortable

This post was written by Alison Green and published on Ask a Manager.

A reader writes:

I want your help in understanding what, if anything, I can/should do about the way my boss talks about herself. I like my boss, but it’s exhausting!

My organization recently went through huge layoffs, so everyone feels overworked and off-balance. As part of that I got a new boss. I get the feeling she’s nervous about doing a good job, and wants us all to like her. I do like her! But during 1-1s and team meetings, she tends to monologue — and it’s all overly personal, self-deprecating, or sad. Too-intimate details about her personal health, negative comments about her body, “funny” stories about being mistreated as a child, general self-deprecation (“stupid” “failure”). The tone is always light, but these stories are sometimes all strung together, and I find it emotionally tiring!

I’ve struggled with self-esteem in the past (I’m doing much better today) but hearing someone constantly self-deprecate themselves, especially someone who has power over me, brings me back to … less fun times. Every meeting where she does this, it takes a lot out of me. It’s as if she thinks these things are normal, or a way of putting herself lower down so that we’ll like her more — but the more it drains me, the more I’m starting to brace myself to be around her.

Approaching her directly: I think she would be horrified to know this affects me, but sometimes people react unexpectedly to things like this and get weird/cold — if she doesn’t have the emotional awareness that this is not good, could this rebound on me in some way? She might stop if I asked her, but I think she would feel really bad … and can I even ask her to stop, if it’s only me having a problem with it? What if she feels uncomfortable around me forever? Or if it affects her treatment of me? What if she tries and fails, and then is apologizing to me on top of the self-deprecation?

Talking to my skip-level is another option. But would it make my boss feel even more paranoid that an unknown “someone” doesn’t like her, as if I were leaving a negative note on her chair? My skip-level is in all these meetings and doesn’t try to correct it — he’s a bit oblivious to social cues, I think. I know my skip-level well and he’s a supportive boss who advocates for his staff and would take this seriously — both for my sake and for my boss’s — but he also has a tendency to interrupt people and publicly correct them in meetings in ways that he really shouldn’t. “You shouldn’t have made this mistake…” “We talked about you not doing that, why did you do it?” What if he starts correcting her about this in front of all of us? Horror…

But I do not dream of labor, much less emotional labor on top of labor! Should I start with her privately, then continue to my skip-level if that doesn’t work? Talking to HR is the nuclear option, so I would want to leave it for last. I think I’m overthinking all this, and possibly thinking about my boss as too fragile, but this situation is definitely bringing up old feelings / maladaptive instincts from my distant past that served me once but no longer do.

Oh, this sounds really uncomfortable. And when I imagine what it might be stemming from in your boss — ugh, it’s just bad all around.

I’m curious about whether you might get some traction by changing the responses you’re giving in the moment when it’s happening. For example, when she tells a “funny” story about being mistreated as a child, what if you said, “That’s really sad, I’m so sorry that happened”? When she calls herself “stupid” or a “failure,” could you say, “It makes me feel terrible to hear you say that”? if she makes a negative comment about her body, what if you said, “I don’t think any of us should talk about bodies that way”? Basically, let your natural reaction show. Look stricken! Respond accordingly. It might make her realize that these stories and comments aren’t landing the way she wants them to.

I’m also curious about whether your coworkers are picking up on the same things, and whether there might be room for the group of you to collaborate on how to respond when it happens.  Depending on the dynamics you have with her, you could even say, as a group, “Hey, we don’t like the way you talk about yourself, please don’t do that.”

If that doesn’t work, I do think the next step is to talk to your skip-level, especially since it sounds like you have a good rapport with him. Yes, that might mean that he corrects her publicly … but that might be what it takes to get this to stop. It would be better if he had the skill to handle it privately (and maybe it’ll turn out that he does) but I’m more concerned that your boss hears that she needs to stop doing this, even if it’s not delivered with perfect delicacy from above.