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The Male Gaze, Averted
You should definitely not let it go. Especially, as you say, because it’s eroding your self-confidence. That’s an enormous red flag and one that you’re not going to be able to ignore, or wish away, without addressing it head-on. I think you’re right in assuming that your boss’s tendency to render you invisible is subconscious, but that doesn’t make it OK. (Multiple times a day!?) Men with the best of intentions and progressive “politics” can also be sexist or behave in sexist ways.
A few questions: What, exactly, is your relationship with the principal of your firm? Have you ever had any “hard” conversations with him in the past? How did he react? This could tell you a lot about how he might respond to a more pointed conversation about your personal feelings within the professional setting he has created.
Also: How many other women work in your company, and at what level? Have you ever had a discussion with one or more of them about feeling invisible in the presence of male colleagues? If not, why? In initiating a discussion with one or more of them, you’ll no doubt learn a lot about what your boss’s interactions with other women are like, and how those interactions are understood and received.
It’s important to phrase and communicate your feelings in a way that puts the focus on just that — your feelings — rather than on his actions. This a fine line to walk, I know, but it’s important because it will help you avoid a situation in which your boss feels attacked or criticized. Try to frame your comments in terms of the discomfort that you feel rather than the egregiousness of what he’s doing. (“In group work settings, I sometimes I feel invisible, especially compared with our male colleagues,” you might say. “I’d like to have a more direct back and forth with you.”) In this sort of formulation, you’re “owning” your feelings rather than making accusations, which can lead to defensiveness or shutting down altogether.
As for when to mention it, well, I’d tack it onto the end of a one-on-one conversation about work that’s already in progress. This allows for the actual “work” aspect of the meeting to be addressed and left uncomplicated by a more difficult discussion. And it gives him some breathing room after the meeting in order to process what you’ve just told him, because he’s going to have to sit with it. No one wants to hear that they’ve hurt someone else’s feelings, and the added gender aspect of it will most likely throw him for a loop, based on what little you’ve said about him. But I hope he’ll take your comments seriously and start to be a little, or a lot, more self-aware about his behavior vis-à-vis you and male colleagues, both in groups and outside of them.
Calling Out a Bully
Oof. This is … a lot. First, I’m sorry you have to deal with this. (I’ve been there, to a certain degree. And someone being smart has nothing to do with whether they are toxic.) Second, I don’t feel strongly enough, or know enough, about the experiences of your female colleagues to be able to respond with any confidence as to whether their gender has anything to do with your boss’s behavior, though I’ve seen evidence of this with my own eyes in a few jobs I’ve had over the decades.
But to address the meat of your comment — I think that talking to your boss about his behavior will only engender more of what you describe as contempt and aggression, so don’t even think about doing it. He’s shown you who he is, full stop. What you have to do is figure out how to take it from here.
One: I would not seek out potential incoming employees to share your observations and experiences with but I also wouldn’t hold back if asked. It also doesn’t sound like you’re particularly anxious to leave — you say “at some point” — but I think you should take into consideration just how much longer you’re willing to tolerate your boss’s toxicity. It sounds like a challenging place to work at.
Two: If you’re not documenting your boss’s behavior, start doing so. Now.
Three: You mention that you’ve helped build your company from its start-up days to where it is right now, which, as you describe it, is a positive place. From this vantage point, I think your experiences will count for a lot, even to the “top dog” you mention your boss has wrapped around his finger. So I’d seriously consider communicating with this higher-up both face to face and with a follow-up email reiterating your observations about your boss. If this top dog has concern for the future of the company — it’s possible that your boss’s behavior could be grounds for a lawsuit — he or she will take what you have to say seriously. I also don’t think it can hurt to point out that the top dog probably isn’t aware of how your boss behaves precisely because your boss puts on a much different, more manager-competent face when the top dog is around.
I don’t believe that your boss, whom you describe as smart, doesn’t know what he’s doing. I think he probably knows, but can’t help himself, which is not so much an excuse as it is a piece of information you can use to your advantage when talking to the higher-up(s) or to human resources. It’s one thing for toxicity to exist in a workplace; it’s quite another when it’s unmistakably pathological. There should be no tolerance for bullies in the workplace, no matter how successful their other contributions may be.
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