my boss overshares, makes sex jokes, and gives me unsolicited birth advice

A reader writes:

I work at a feminist tech company. Our app is focused on sex and intimacy. We’re a very small team, primarily remote, but every month we have an in-person get-together and workshop. The issue is with the CEO of the company, who also oversees all the engineers. I’m not an engineer and I don’t report to him, but I am in a director role and the nature of my job does mean that I have to talk to him a lot. For the most part, I respect this man professionally. I think he leads the engineers well, and he takes my advice seriously when it’s about something I’m clearly the expert in.

However, he’s a chronic over-sharer, discusses things that make me uncomfortable, and most recently, after I’ve told the company I’m expecting a child, has started giving me unsolicited birth and parenting advice. I’m writing this the day after he started telling me about the benefits of home birthing over hospital birthing, which I felt was a step too far — no matter what your stance is, it feels very out of bounds to weigh in on your employee’s birth plan when she didn’t ask! The first time we met in person he told me about the problems in his marriage and his ethically non-monogamous / swinger lifestyle. He also makes dirty jokes (admittedly to everyone, not just to me!), and yesterday also told me about the softcore “porn with plot” books he enjoys reading.

I know we work on a product that is related to sex, so some of these have come up in a way that was at least vaguely related to a work discussion. But I haven’t found that anyone else in the company takes the conversation to uncomfortable places quite as often. We all make jokes and have a pretty convivial vibe (which I like!), but it’s starting to get out of hand. I do find his personality in general just not to my taste, which I worry colors my experience of him, and I also recognize that I’m generally more reserved and less “free” — I don’t like discussing my sex life or bodily functions even with my friends, I’m not somebody who enjoys physical contact, and, while I’m super excited for the baby, I’m just not the kind of person who enjoys discussing symptoms / supplements / birth / etc. with anyone, let alone the CEO of my company!

I have made it pretty clear (in my opinion, at least) that I am, for lack of a better word, a “prude” and clarified that I wasn’t really the kind to talk about my pregnancy at work, but it hasn’t stopped. I look visibly uncomfortable when these things happen, but that doesn’t put a stop to them. Most of my exposure is limited to these monthly in-person events, but it’s wearing on me.

He’s open about being neurodivergent, and he takes criticism really personally. I’ve seen him get extremely touchy when someone gives feedback on the app or disagrees with him in a meeting. The people I’d otherwise complain to — those I work with directly and my manager (who is also our sole HR person) — are extremely close with him. Some are even family. It feels like it isn’t an option because of the years-long personal relationships they have.

I love my job. I really love the company’s mission, I like the team I work with. Being fully remote is an absolute godsend which means I’ve been able to move closer to my family and enjoy sunny weather all year round, I am paid well, and I find my work really fulfilling. This isn’t a bridge I want to burn, or a job I want to leave.

I’m keen to set some boundaries, but I’m nervous about the fallout, and have really no sense of how to at this point!

I wrote back and asked, “When you told you him you didn’t want to talk about your pregnancy at work, do you remember exactly what you said? And what did he say in response?”

Admittedly, I was way lighter than I wish I’d been in hindsight. I’d told him and my manager because they were senior leadership, and I wasn’t keeping it a “secret” anymore at all (I’m six months along, so really starting to show anyway).

He mentioned me “having a child soon” loudly enough in a small group setting that I felt a little obliged to share and say, “I’m having a child,” etc. (this was a little annoying, but I did tell him that it was okay to let people know and not treat it like a secret, so that’s on me). When people started congratulating me, I took the opportunity to say, “Thanks so much — I’m really excited! Although I’ve really learned about myself that I find talking about it quite embarrassing, haha.” I can’t remember whether he reacted specifically because this was said to the group, but he launched into full pregnancy stuff straight afterwards, asking me about cravings and recommending a supplement for thrush (?).

Regarding the other stuff, I know he knows it makes me uncomfortable because 1) I say stuff like, “Oh, I’m just quite prudish, isn’t that ironic given our industry” a lot and 2) he’s poked fun of me for tuning out during an extended dirty joke bit a few of my colleagues were doing.

Okay, yeah, I think you were not really as direct as you’ll need to be with him. He’s not picking up on “I find it quite embarrassing to talk about” (whether that’s pregnancy, or describing yourself as “prudish” about sexual humor or so forth) or uncomfortable looks and is going to need you to say, more or less, “Please do not do this.”

Specifically, the next time he crosses boundaries about pregnancy and birth, say this: “I really don’t want to talk about it at work, thank you for understanding.” And if he continues: “I’m sorry if I wasn’t clear — this topic is completely off-limits for me at work. I am just not comfortable with it and need to change the topic.”

Similarly, if he ever again says anything about problems in his marriage or his non-monogamous relationships or swinging (!) or the soft porn he likes to read, say, “I need to stop you there — this is way too personal and I am not comfortable hearing it at work.”

The next time he makes a dirty joke, say, “I really don’t like hearing dirty jokes at work. Please don’t make them around me.”

I know you’re worried because you’ve seen him react badly to criticism, but (a) this isn’t criticism; it’s you setting a boundary about what discussions you will have at work and (b) because hints haven’t worked, a direct “I’m uncomfortable; please stop” is the only effective way to deal with it. If he’s otherwise a decent guy, he might be embarrassed in the moment or even feel stung, but that’s okay and he will get over it. If he gets angry or holds it against you, then he’s really not a decent guy and it’s better to get clarity on that sooner rather than later anyway.

You might also consider confiding in some of the people you put in the category of “people I’d complain to if they weren’t so close to him.” It doesn’t need to be a formal complaint (although you certainly have standing for it to be); it could simply be, “I’m really having trouble with this and wonder if you can back me up when those topics come up.” If you frame it in terms of asking for their help, it might be pretty effective … and if they’re close to him, they likely know he’s like this and know it doesn’t land well with everyone. The fact that they’re close could actually make them more comfortable helping to manage this aspect of his work behavior once they know there’s a need to. (Or, of course, it might not — but it’s a reasonable thing to ask for advice on and for help with, and it shouldn’t blow up your relationships there unless this company is so dysfunctional that the relationships aren’t especially worth saving anyway.)

You can do all of the above despite working on a product that’s related to sex. When your work intersects with sex in some way, it does mean that there will be more sex-related topic in your office than there otherwise should be — but it should be work-related sex talk, and this is not.

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