TL;DR: Use these skip level meeting questions to build trust without undermining the manager in the middle. Managers should ask about work, support, culture, and growth—not run a secret performance review. Employees should prepare upward questions that clarify strategy and blockers. Share intent beforehand, protect confidentiality, and follow up on themes. Aim for a quarterly cadence when your span of control allows it.
A skip-level meeting is a conversation between a leader and someone two (or more) layers down—without that person’s direct manager in the room. Done well, it surfaces reality. Done poorly, it turns into a kangaroo court. This list of skip level meeting questions is built for both sides: what managers ask, what employees ask, and how to stay out of the common traps described by resources like The Management Center’s skip-level toolkit and the GitLab Handbook skip-level guidance.
What a skip-level is (and is not)
The Management Center defines it as a one-on-one between a manager and a staff person they do not manage directly—usually a direct report of someone they do manage. GitLab adds that skip-levels should help the wider team communicate with senior leaders, not replace 1:1s or “go around” a manager to check performance in secret.
| Do | Don’t |
|---|---|
| Explain the purpose to managers and staff beforehand | Hide the meetings or spring them as surprises |
| Listen for themes; coach the middle manager later | Overrule the manager lives in the room |
| Protect individual confidences | Quote people back to their boss by name |
| Meet equitably (everyone or a fair rotation) | Only skip with favorites or complainers |
| Follow up on commitments | Collect feedback and vanish |
How managers should open the meeting
- State why you do skip-levels (relationships, insight, transparency).
- Say what you will and will not do with the information.
- Invite honesty, then stay in listening mode unless they ask for problem-solving.
- Leave 15 minutes after each meeting to capture themes, as The Management Center suggests.
20 skip-level questions for managers to ask
Mix rapport, manager-support, and org-insight prompts. Prefer open questions over yes/no.
- 1. What brought you to this role or team?
- 2. What is the best part of your work week right now?
- 3. What is draining more energy than it should?
- 4. What does great support from your manager look like for you?
- 5. What is the best part of working with your manager?
- 6. What is the hardest part?
- 7. What do you wish your manager did more of—or less of?
- 8. Tell me about a recent situation you wish had been handled differently.
- 9. How clear are priorities when work collides?
- 10. Where do you need more autonomy, and where do you want more guidance?
- 11. If you could fix one process, what would it be and why?
- 12. Which team or company value do we live every day—and which do we miss?
- 13. What is something you see from your seat that I probably do not see from mine?
- 14. Where are we making decisions too slowly—or too fast?
- 15. What would help you do the best work of your career here in the next year?
- 16. Who on the team is doing under-recognized work?
- 17. What should I stop, start, or continue as a leader of this org?
- 18. How are cross-team handoffs going from your point of view?
- 19. Is there anything you have been hesitant to raise that I should hear?
- 20. What should I make sure we cover next time?
Those prompts echo themes in The Management Center’s sample table (rapport, manager feedback, organization feedback) without turning the chat into an interrogation.
20 skip-level questions employees can ask upward
Employees freeze when they only answer. Bring a short list. GitLab notes skip-levels are also for clarifying objectives and asking questions—not for handing your career plan to your boss’s boss.
- 21. What does success for our team look like over the next two quarters?
- 22. Which company priorities should shape how I say no to work?
- 23. Where do you want more visibility into our team’s work?
- 24. What risks keep you up at night for this function?
- 25. How should I escalate when my manager and I disagree on priority?
- 26. What skills will matter most on this team a year from now?
- 27. Are there projects where you need volunteers from our level?
- 28. How do you prefer to hear bad news?
- 29. What is one thing leaders think is clear that still confuses the floor?
- 30. How should we measure customer or user impact, not just activity?
- 31. Where can individual contributors influence strategy—not only execute it?
- 32. What does “good upward communication” look like to you?
- 33. Which meetings or rituals would you trim if you could?
- 34. How are you thinking about hiring versus capability building on this team?
- 35. What support should I ask my manager for before I come to you?
- 36. How do skip-level themes usually get acted on here?
- 37. Is there context about org changes I am missing?
- 38. Who else should I build a relationship with across the company?
- 39. What would you want to know if you sat in my role for a week?
- 40. How can I make these skip-levels useful for you, not only for me?
Cadence and format tips
GitLab recommends at least quarterly skip-levels, one-on-one or in groups of no more than about 10–15. The Management Center suggests aiming for twice a year with each person, or quarterly if the group is small, and meeting everyone rather than cherry-picking. Large orgs can rotate cohorts so coverage stays fair. Do not record the meeting if trust is the point—GitLab explicitly avoids recording skip-levels.
After the meeting
- Send a short thank-you.
- Repeat key themes and any commitments you made.
- Share generalized insights with the middle manager to help them grow—without burning the source.
- Encourage staff to raise manager-specific issues with their manager when it is safe and appropriate.
Skip-levels pair well with strong everyday delegation habits. If your managers struggle to hand off work cleanly, point them to our guide on how to delegate tasks effectively and the practical how to delegate a Gmail account walkthrough for ops-heavy roles. For a sharper org-design lens, see whether software or strategy is the bigger problem.
Bottom line
Great skip level meeting questions open with trust, dig into support and systems, and leave room for the employee to ask upward. Forty prompts are plenty—pick eight to ten per meeting. Tell people why you are meeting, never use the session to ambush a manager, and close the loop so the next skip-level is easier than the last.
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