The conversation your org chart doesn't naturally make room for. A skip level is a direct conversation between a leader and someone two or more rungs below them, an executive talking with an individual contributor without their manager in the room. Not behind the manager's back, the point is to skip a layer of filtering, not to go around anyone.
Every layer of management filters information a little, usually with good intentions. That also means the people at the top can go a long time without hearing what's actually happening on the ground. Skip levels are how you hear it directly, on a regular cadence, before it becomes a surprise.
- Set a real cadence. Quarterly works for most orgs, or triggered when someone joins a new team. Sporadic skip levels read as inspections, not relationships.
- Tell the manager it's happening. Always, before it happens. Secrecy is what turns a skip level into something political.
- Let the employee lead. Open questions, real silence after you ask them. If you're doing most of the talking, you're doing it wrong.
- Take notes, protect the source. Write down themes you can act on. Don't repeat specifics back to a manager in a way that makes it obvious who said what.
- Close the loop. If you can influence something that came up, follow up on it, and let the person know you did. That's what makes the next one worth showing up to.
A starting set of open-ended questions across four areas. Swap in your own before your next round of meetings.
Build the room
- How's it going, really, not the elevator version?
- What's something you're proud of from the last few months that nobody's asked you about?
- What would make the next hour worth your time?
The role itself
- What's taking up time that shouldn't be?
- Where do you want to be in a year, and what's in the way of that right now?
- What would you change about your role if you could change one thing?
What's it like day to day
- Do you feel like you get useful feedback, and often enough?
- What does your manager do that you wish more leaders did?
- Is there anything slowing the team down that leadership doesn't seem to see?
The bigger picture
- What's something people talk about privately that never makes it into an all hands?
- If you were running this place for a day, what's the first thing you'd fix?
- What would make you seriously consider leaving?
Keep it thin. Themes and commitments, not a transcript.
| Date | Person | Key theme | Follow-up action | Status |
|---|---|---|---|---|
| Mar 4 | J. Alvarez | Wants more context on roadmap priorities before sprint planning | Add a 10 min roadmap recap to sprint kickoff | Closed |
| Mar 4 | R. Chen | Feels growth path is unclear past senior level | Loop in HR on a staff level rubric | In progress |
| Mar 5 | T. Boone | On call rotation feels heavier on their sub team than others | Pull on call hours data across teams to check | Open |
- Ask one real follow-up question and then stop talking, silence does the work.
- End by asking what they'd want you to remember from the conversation.
- Send a short thank-you afterward, it costs nothing and it's rarely done.
- Don't turn it into a performance check-in, that's what the manager relationship is for.
- Don't promise something you can't actually influence.
- Don't skip the follow-up, a skip level with no visible action becomes a box-checking exercise fast.
The download includes a second tab, "Why & How to Use," with the same guidance above plus the use cases, so you don't have to come back to this page before your next round.