In partnership with
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.
A thank you from this week’s sponsor:
You Can't Automate Good Judgement
AI promises speed and efficiency, but it’s leaving many leaders feeling more overwhelmed than ever.
The real problem isn’t technology.
It’s the pressure to do more with less — without losing what makes your leadership effective.
BELAY created the free resource 5 Traits AI Can’t Replace & Why They Matter More Than Ever to help leaders pinpoint where AI can help and where human judgment is still essential.
At BELAY, we help leaders accomplish more by matching them with top-tier, U.S.-based Executive Assistants who bring the discernment, foresight, and relational intelligence that AI can’t replicate.
That way, you can focus on vision. Not systems.
Come prepared with 1–2 topics
Don't walk in empty-handed. Pick one or two things you actually want to discuss: a project you're leading, your career goals, a question about where the org is headed, or something you've noticed that might be useful for them to hear. You don't need a deck. You need a clear point and maybe a sentence or two of context.
If there's something you want them to read beforehand—a brief doc, a link to a launch, a short update—send it in advance. Skip-levels are usually time-boxed. Giving them a chance to skim before the meeting means you spend less time on "here's what this is" and more time on the conversation. It also signals you're serious about using the time well.
Stay out of the weeds
Give them the shape of the work: what you're focused on, what's going well, what's hard, and what would help. The play-by-play of your last sprint or the details of a bug you fixed—skip that. If you're explaining architecture or walking through a ticket list, you're too deep. Pull up a level.
For instance, we're doing a heavy AI enablement push at Zapier, and I might speak with my skip-level about how that push is being perceived by my teams—adoption, skepticism, where people are excited or stuck. That's the org-level insight they find valuable. Not "we built this specific Claude skill and here's how it works."
What's the outcome? What's the one thing they should know or do with what you're sharing? That's the version that's useful for someone who's not in the day-to-day with you.
What they're usually listening for
It helps to know what's in it for them. They're often trying to hear how initiatives are landing, spot blockages, and get a sense of who's doing interesting work. So when you pick your 1–2 topics, lean toward things that give them that: how your team is responding to a change, something you'd want leadership to know that doesn't always make it up the chain, or a win (or lesson) that's worth highlighting. You're giving them signal they can't get from a status report.
Skip-levels don't have to be weird. Show up with 1–2 topics, share context ahead of time when you can, stay high level, and don't use the room to go around your manager. Do that, and you'll leave with something more useful than "that was fine, I guess."