Skip-level meetings can feel awkward. You're in a room with your boss's boss. You don't report to them. You're not sure what they want, and you don't want to waste their time or yours. So you default to small talk, or a vague "things are going well," and you leave wondering what the point was.
I've been there. The fix is to show up with a clear sense of what the meeting is for and a little bit of prep—not to avoid the meeting or hope they drive it.
What the meeting is for
A skip-level is a chance for someone higher up to hear the pulse of the org—how strategy lands on the ground, what's working, what's sticky, and who's doing what. They're also often trying to put faces to names and get a read on talent. So you're not there to replace your 1:1 or to get day-to-day direction; that stays with your manager. If you show up with that in mind, you can shape the conversation instead of waiting for them to fill the silence.
Don't use the meeting to air grievances about your manager or go around them. You can be honest about how things work, such as processes, blockers, how information flows, without making it personal. If something's broken at the org or team level, you can name it. If you're frustrated with your direct manager, that's a 1:1 conversation or a different channel. Skip-levels work when they build trust. Going around your manager usually does the opposite, and they'll wonder what you say about them when they're not in the room.
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