Let's be clear, though: I'm not her boss. She's two levels below me and not in my direct chain of command, currently. I'd actually be less down on it if I we

Let's be clear, though: I'm not her boss. She's two levels below me and not in my direct chain of command, currently. I'd actually be less down on it if I were her boss, and she was speaking just to me, seeking advice or something. There's a sort of "Let's have an open discussion about career stuff" venue in which you kind of agree to suspend judgment. Just randomly dropping that factoid in a group discussion where it's difficult or impossible for me to probe deeper and understand what's behind it is not a great idea. That makes it easier for someone to take a bad impression from it. But, also, yeah, I agree, your boss is never fully your friend. I like a lot of the people who work for me, and in other circumstances I think I could be friends with most of them, but part of my job is to evaluate them, including negatively. There is an art to expressing vulnerability in a way that creates intimacy without making a person question your abilities. You can't just assume that everything that you say will have only positive consequences.