Can I be friends with my direct reports? Is it okay to hang out with them or is that a boundary violation? Am I not like regular moms — am I a cool mom?

Emma: There aren’t really rules for this stuff — at least, I’ve never worked in a place that’s tried to define friendship and platonic boss/subordinate relationships.

Andy: No rules! No rules! My neighbors used to chant that every weekend before they would party. It always seemed like the beginning of a bunch of bad ideas… But, yeah, it’s really your call. We can’t tell you whether or not it’s crossing a boundary to hang out with your team outside of work.

Emma: Or provide Official Answers to other cool-mom questions I’ve asked myself over the years: What subjects are off limits to talk about? If I’m friends with one person, do I have to be friends with the whole team? Do my reports even want to be friends with me?

I’ve asked these questions because I definitely have had the impulse to be friends with the people I’ve managed. For most of my career I’ve worked in tech-adjacent companies with flat orgs and young, vibrant employees. Often, friendship felt inevitable after working long hours for weeks on end alongside people I really liked. Not connecting on a deeper social level would have taken more energy and intention that I wanted or knew how to give.

Andy: Yes, definitely. When you’re with cool, smart people all day, it’s natural to want to be friends. But it’s also tricky. The goody-goody rule follower in me says: No friendship! Too risky! Danger! Danger!

Emma: I don’t think we need to spend too long discussing the risks of getting really close with the people on your team. They are all fairly obvious. You’re vulnerable to accusations of special treatment — both perceived and real. You’re obligated to keep secrets from them, or risk losing your job.

Andy: You’ll be in the room when you have to decide that your friend is the one getting laid off, or deliver the news that they’re getting passed up for a promotion, or you don’t think they deserve the raise they want. The list goes on. All the hard parts of managing get that much harder when the person is your friend.

And there are so many other places to find friends. Join a hiking club! Or a book club! A community garden! Get really into a Reddit forum! Go out with your co-managers! I say steer clear of your team. I don’t typically befriend my reports, and I especially didn’t when I was first managing. I wasn’t angsty or rude — at least, I tried not to be — but it was already hard enough to understand the basic manager-report relationship without complicating it more.

Emma: The best blanket “rule” I’ve been able to come up with is to be friendly with your direct reports, but not friends. If you can do that, you will stay safely appropriate and I think you will be satisfied with the relationship.

Have I followed this rule throughout my career? Absolutely not. Do I regret it? No way — I love my friends! Has that led to some awkward situations that kept me up at night? Of course.

One thing that’s helped me navigate friendships with my team members is simply following their lead: responding instead of initiating. I won’t ask you about your dating life, but I’m delighted to chat about what you’re going to wear on Friday’s blind date. I’m not going to surprise show up at your community theater production of Grease: The Musical, but if you invite me, I’ll at least check my calendar. What can I say? I love musicals!

Andy: Oh, that’s super interesting. I take a harder line: I’m definitely going to squash the Tinder talk and am pretty much a guaranteed no on the musical. I’ll smile, ask questions about rehearsal, do my best to notice when you’re dragging and might need to take a half day, but that’s it. I’ve gone to the equivalent to the musical before and it just felt too complicated.

Emma: That makes sense. It sounds like you know your own boundaries, and I think that’s as important as knowing and respecting your team members’ boundaries. Over the years, I’ve gotten much better at understanding the information that will impact my perception and trust of my team and their work, and then making sure I stay out of situations where that information is present. If the vision of your new hire doing a lot of pelvic thrusts dressed as Danny Zuko is going to haunt you, skip the show. If it’s going to bum you out seeing your top performer black out and puke on their shoes, for god’s sake, don’t go to any holiday afterparties.

Andy: Yes. To sum up my stance: friendships take a lot of work. Complex friendships, like the one between a manager and her report, take even more work.

I say all this, and feel I should confess to our dear readers that I became friends with you, Emma, when you were my report.

Emma: It’s true! I win!

Andy: Lol I for sure don’t regret it — and it also never felt that complicated. I think there are lots of extenuating reasons for why that might be: I was on a short-term contract and you were going to take over my role; we worked together practically non-stop; I thought of you as my partner more than my report.

Emma: Any maybe you just can’t stop true friendship.

Andy: Who am I to say no to destiny?

Emma: It makes me glad there are no strict rules governing interoffice friendships, even though neither of us recommend actively seeking friendship with your reports.

Andy: There’s another way you may “become” friends with your reports: when you get promoted and suddenly find yourself managing your former friend group, which is what one of our readers wrote in asking about last week. It’s a challenge worthy of its own newsletter. We’ll be tackling it next week.

Emma: ‘Til then!

Good Boss Achievement Stickers: BFF Edition

The Bent Good Boss Achievement Stickers BFF Edition