Q I work in a small office (nine employees) with a tight-knit, friendly culture. I am a 32-year-old woman. The principal of the firm is a man in his 60s who is generally well intentioned. I know he holds progressive values, and is not an outright misogynist. But the thorn in my side is that he exclusively addresses (and makes eye contact with) my male colleagues (with whom I am at equal status, organizationally) when we are in a group. When we are one-on-one, he can make eye contact with me, but if there is another man in the room, I feel invisible; we will go the entire conversation, and he will not look at me once. This feels particularly egregious when he looks at my male colleagues while responding to a question that I asked. This happens multiple times a day, and it is wearing on my self-confidence. Should I mention this perhaps subconscious habit to him, or just let it go?

— Anonymous

A 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’ tendency to render you invisible is subconscious, but that doesn’t make it OK. Men with the best of intentions and progressive politics can also 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? 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 any of them about feeling invisible in the presence of male colleagues? If not, why? In initiating a discussion, you’ll no doubt learn a lot about what your boss’ interactions with other women are like, and how those interactions are understood and received.

It’s important to communicate your feelings in a way that puts the focus on 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 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.

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 to process what you’ve 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.

Anna Holmes is an award-winning writer, editor and creative exec whose work has appeared in numerous publications, including the New York Times, Washington Post, and The New Yorker.