Business
20 skip-level meeting questions that lead to a useful conversation
Stefan Weiss
The most useful skip-level meeting questions connect a concrete experience to something a senior leader can clarify, influence or follow up. Ask about direction, obstacles across teams and the support needed to do good work. Bring a small number of relevant questions and leave time to explore the answers.
A skip-level meeting usually brings an employee together with their manager's manager, without the direct manager attending. It can help both people understand work beyond the normal reporting relationship. It should have a clear purpose, including what may be shared afterwards.
GitLab's public handbook describes skip levels as a way for senior leaders and indirect reports to communicate, build rapport and discuss company direction. It distinguishes that purpose from taking over a direct manager's responsibilities. Read GitLab's overview. Your organisation may use a different format, so check the invitation and local expectations first.
The questions below are original suggestions for employees and senior leaders. They are selected for three reasons: they invite a specific example, address something relevant to the other person's role and create a possible next step. They are not a script to complete in one sitting or a ranking based on measured performance.
Choose the right questions for this meeting
For a first conversation, start with context and mutual understanding. For a recurring meeting, bring one development since the previous discussion and one issue that would benefit from the leader's perspective.
If you are the employee, choose two or three questions from the first twelve. If you are the leader, choose a few from the final eight and make room for the employee's agenda. The number is a practical starting point, not a rule about how much a good meeting must cover.
Prefer a question you can connect to a real example. “How do we improve communication?” is hard to answer usefully. “When two teams give us conflicting priorities, who should resolve the trade-off?” points to a decision and a process.
Questions employees can ask about direction
1. Which outcome should our team protect when priorities compete?
Use this when several requests appear equally urgent. Bring a specific trade-off rather than asking the leader to repeat the company strategy. A useful follow-up is to ask how that priority should be communicated back through your manager.
2. What has changed in the wider organisation that we may not yet see?
This invites relevant context about customers, dependencies or strategy. It does not require the leader to disclose confidential plans. Ask which part of the context should change how your team approaches its current work.
3. Where does our team's work contribute most to the next company goal?
Use this to connect everyday effort with the wider outcome. Offer a brief description of what you are doing, then check your understanding of the connection. If the answer is unclear, agree where the team should seek more detail.
4. What would make you reconsider the current direction?
This asks about assumptions and signals rather than demanding certainty. For example, a leader might need evidence about customer adoption before revisiting a plan. Clarify which signals the team can usefully observe and which decisions remain outside its remit.
Questions employees can ask about obstacles and support
5. Which cross-team dependency should we raise earlier?
Bring a recent example of a dependency becoming urgent too late. Ask what an earlier signal would look like and who needs it. This gives the leader something more actionable than a general complaint about another department.
6. Who can resolve a priority conflict that spans two teams?
Use this when the normal team-level route has not resolved a recurring conflict. Describe the competing requests and their effect on the work. Seek a clear route for a decision, then keep your manager involved through the agreed process.
7. What should we stop doing to make room for this priority?
This is useful when new work arrives without a corresponding capacity decision. Offer a concrete trade-off. The desired answer is a clarification of what can change or who can decide, not an informal promise that the team will absorb everything.
8. What evidence would help you assess this obstacle?
Ask this when you can describe a problem but do not yet have enough information to support a broader conclusion. Agree what to collect, from where and for what purpose. Avoid gathering personal or sensitive material simply to make a concern look more convincing.
Questions employees can ask about growth and follow-through
9. What capability will become more valuable as the team develops?
Use the leader's broader perspective to understand future needs. Ask for an example of where that capability would help. Discuss personal development commitments with your direct manager through the usual process rather than treating the skip level as a separate career agreement.
10. What work would help me understand the wider business better?
This can open a conversation about exposure to customers, another function or a decision process. Keep the request specific enough to assess. A useful outcome may be a suggestion to explore with your manager, not an immediate new assignment.
11. How would you prefer us to raise an emerging concern?
Ask about the appropriate channel, useful context and expected response. Routine operational issues and sensitive personal concerns may require different routes. Do not assume that access to a senior leader replaces the organisation's established support or reporting channels.
12. What should we each take away, and when should we revisit it?
Use this near the end. Separate information, proposed work and accepted commitments. If the leader needs to consult someone else, record that consultation as the next step rather than describing the underlying request as approved.
Questions senior leaders can ask to understand the work
13. Which part of your work is harder than it appears from my level?
Invite one recent example and ask what made it difficult. Avoid jumping immediately to a solution or asking the employee to speak for everyone. The value is the perspective you may be missing, including where your current picture is incomplete.
14. Where do our stated priorities conflict with what the team is asked to do?
Ask for the competing expectations and their source. Check your understanding before judging the conflict. You may discover a communication gap, a genuine capacity problem or a local interpretation that needs clarification with the manager.
15. Which decision is taking too long, and what is waiting on it?
This focuses on a concrete bottleneck. Establish who currently owns the decision and what information is missing. Do not take ownership automatically: sometimes the useful intervention is to clarify a decision route or unblock an existing owner.
16. Whose contribution deserves more visibility, and why?
Ask for the contribution and its effect, not a popularity nomination. This can reveal useful work that routine reporting misses. Verify the context before making a public attribution or sharing details with a wider audience.
Questions senior leaders can ask about feedback and action
17. What could I explain more clearly about our direction?
This makes the leader's own communication available for discussion. Ask which message was difficult to apply and where the uncertainty appeared. Rephrase what you heard before offering another explanation, so the employee can correct your understanding.
18. What is one small change we could investigate to improve the work?
Keep the request open to observation rather than requiring a polished proposal. Ask who would need to be involved and what would count as a useful result. Investigation is a valid next step when an immediate commitment would be premature.
19. What do you want me to understand before I respond?
Use this when a concern has important context or your first reaction is to defend the existing approach. Give the employee time to finish. Then describe what you understand, what remains uncertain and what you can reasonably do next.
20. What may I share, with whom, and what should we clarify first?
Ask before circulating feedback. Explain any limits on what you can keep confidential and follow the organisation's process. Agree the wording of an ordinary action recap where appropriate; do not promise secrecy that your role or the situation does not permit.
Prepare an example, a question and a useful outcome
You do not need a presentation to make the conversation worthwhile. Prepare three short elements for each topic:
Example: What happened, and what did you observe directly?
Question: What do you need the other person to clarify or consider?
Useful outcome: What would help you move forward after the meeting?
For example, an employee might bring this fictional situation: two teams requested the same delivery week, the conflict remained unresolved at their normal planning meeting, and both requests were still treated as priorities.
The question could be: “Who should decide which outcome takes priority when these requests conflict?” A useful outcome is an agreed decision route. It is not a guarantee that the employee's preferred project will win.
A senior leader can prepare by reviewing the employee's context, known contributions and previous accepted follow-ups. GitLab's engineering guidance describes preparation and recognition as part of its own skip-level practice. It also explicitly explains when feedback may be shared with a manager. See the engineering team's guidance. Treat that as an example of a disclosed process, not a policy that automatically applies to your company.
A simple agenda for a 30-minute conversation
Use this as an adjustable starting point:
First five minutes: confirm the purpose, context and any expectations about notes or sharing.
Next fifteen minutes: explore the employee's most useful questions, with concrete examples and follow-ups.
Next five minutes: give relevant wider context and clarify what remains unanswered.
Final five minutes: confirm any accepted next steps, ownership and a review point.
If a sensitive or complex issue emerges, it may need a separate conversation through the appropriate route. Do not rush it to fit the agenda or leave an employee believing it has been resolved because the meeting ended.
A regular manager one-to-one serves an ongoing relationship and management purpose. Use our manager one-to-one guide for that different conversation. A skip level should add perspective and a route for communication, not create two competing managers.
Decide what should be recorded before the meeting
Do not assume that a skip-level meeting needs an audio record. GitLab's leadership handbook explicitly excludes recording from its skip-level process to support trust. That is GitLab's policy; establish your own organisation's requirements and the participants' expectations before choosing any tool. See its recording boundary.
For some conversations, a small set of agreed action notes is more appropriate than a detailed record. Clarify what you will note, who can see it and how corrections will be handled. A leader should explain the limits of confidentiality before asking for sensitive feedback.
Weeve can help with preparation from existing material that you are authorised to use. For example, you might review earlier project discussions and draft the open questions you want to bring. Keep the source scope narrow and check any generated account against the underlying material. Explore working with saved recordings.
Genuine Weeve interface capture with synthetic demonstration content. It illustrates an editable proposed document, not a recorded skip-level meeting.
The preparation document remains your draft. It is not evidence that the leader accepted a request, and it should not pull another person's confidential feedback into the meeting without authorisation. Local processing and optional external AI have different data boundaries; check the provider and material before using either workflow.
Close the loop without overstating agreement
Afterwards, keep only the account needed for the agreed purpose. A useful recap distinguishes:
Context received: information the leader explained.
Open question: something still requiring an answer.
Proposed change: an idea someone may investigate.
Accepted action: a specific next step with an owner who agreed to it.
For the fictional priority conflict, the accepted action might be that the leader will identify the decision owner and reply by Thursday. That does not mean the delivery date changed or either request was cancelled.
Share the recap only through the agreed route and invite corrections where appropriate. Our guide to writing a meeting summary explains how to keep the account clear and usable.
At the next meeting, check what happened to the accepted action before introducing a fresh list. A skip-level conversation earns its place through clearer understanding and responsible follow-through, not through the number of questions asked.
