Skip-level meeting questions and how to run them

A skip-level meeting is a conversation between a senior manager and the people who report to their direct reports, without the manager in between in the room. The best skip-level meeting questions ask about recent, specific work: what got in the way last week, what people hear about the plan, what they would change. This guide gives you the questions in six sections with probes, in about 30 minutes, and covers how to run skip-levels without going around the manager.

What is a skip-level meeting for?

It tells a senior leader what the organisation looks like two layers down: which messages arrived, which got lost, what slows the work. GitLab’s public handbook page on skip-levels is one of the clearest written policies. It requires skip-levels for anyone whose reports have reports, at least quarterly, and lists what they are not for: checking on a manager’s performance by going around them, or doing the manager’s job on priorities and careers.

That second list decides whether skip-levels help or harm. Harvard Business Review’s guide to meeting your boss’s boss covers the same meeting from the employee’s side, which is worth reading before you sit on the other side of the table.

How do you run a skip-level without undermining the manager?

Middle managers are already stretched. Gallup found that only 31% of US managers were engaged in 2024. A skip-level that feels like an audit of them makes that worse and teaches their team that the way to fix things is to go over their head. Four rules keep it on the right side:

1. Tell the manager first. Explain what the meeting is for and that you will share themes with them, never who said what.
2. Don’t decide in the room. If someone asks for a rota change or a transfer, say you’ll pass it on to the person who owns it. Then do that.
3. Redirect complaints about the manager to patterns. Ask “What would help your team work better with each other and with your manager?” instead of “What do you think of your manager?”
4. Debrief the manager within a week. Share what you heard as themes, agree what each of you will do, and let the manager tell their team what happens next.

A decision rule that helps with the debrief: one person raising something is a question to explore. The same thing raised in three teams is a pattern you own, and it usually sits above the manager anyway.

Skip-level meeting questions: the guide

Ask about recent moments. “How are things going?” gets “fine”. “What slowed you down last week?” gets the broken scanner and the approval that took four days.

1. Opening (3 minutes)

1. What are you working on at the moment that you’d like me to know about?

Before this, say why you are there: to understand what the work looks like from where they sit, and what you could fix from where you sit. Say that their manager knows about the meeting and will hear themes, not names.

2. The work right now (7 minutes)

1. What slowed you down last week?
2. What’s one thing you do regularly that feels like a waste of time?
3. When did you last have to work around a process or system to get something done?

Follow up with:

• How often does that happen?
• Who else does it affect?

3. Direction and priorities (6 minutes)

1. In your own words, what is the department trying to achieve this year?
2. What have you heard about the plans for next quarter, and where did you hear it?
3. Is there a decision from above that you didn’t understand?

Follow up with:

• What would help it make sense?

This section is where skip-levels earn their time. If three teams describe the strategy three different ways, the message stopped somewhere between you and them. GitLab’s handbook notes that leaders often leave skip-levels saying they thought everybody knew that already.

4. Support and team (6 minutes)

1. Who do you go to when you’re stuck, and how quickly do you get help?
2. What would help your team work better together?
3. What does your manager do that you’d like more of?

Follow up with:

• Can you give me an example from the last month?

The third question is phrased positively on purpose. It gives you useful material for the manager’s debrief without turning the meeting into a review of them.

5. What you would change (5 minutes)

1. If you had my job for a week, what is the first thing you’d change?
2. What’s something we stopped doing that you think was working?

Follow up with:

• What would it take to do that?

6. Close (3 minutes)

1. What do you want to ask me?
2. Is there anything I should have asked and didn’t?

Should skip-level meetings be one-to-one or in groups?

One-to-one gets more detail and more candour about sensitive topics. Groups get more people heard and let colleagues build on each other’s points, though the loudest voice often sets the tone. GitLab allows both and caps groups at 10 to 15 to keep everyone talking. A practical split: one-to-one for a first meeting with someone or after a difficult change; groups of four to eight from the same team for regular rounds. In a warehouse or on a ward, group sessions on shift overlap are usually the only realistic option.

How often should you hold skip-level meetings?

Quarterly is the common baseline, and GitLab sets it as the minimum. If you have more skip-level reports than you can meet in a quarter, rotate: meet a different group each quarter so everyone is covered over the year. Hold an extra round after a reorganisation or a change of manager, when the gap between what you decided and what people experience is widest.

What should you do with what you hear in skip-level meetings?

1. Write notes as themes straight after, without names.
2. Sort each theme by who can act: the manager, you, or someone above or beside you.
3. Debrief each manager on their team’s themes within a week.
4. Pick one or two things you own and do them visibly. Tell people at the next skip-level what changed.
5. Keep a running list across rounds. A theme that keeps coming back is a sign the fix didn’t work.

When is a skip-level meeting not enough?

Picture a regional operations director with six site managers and about 240 people across three warehouses. Quarterly group skip-levels reach perhaps 40 of them a quarter, mostly on day shift, mostly the people who are comfortable talking to the boss. The night shift at the smallest site never gets a slot. Whatever comes back is real, but it is a sample chosen by availability and confidence.

When you need to hear from a whole department at once, for example after a reorganisation, before a new plan or when one site’s turnover starts rising, run an interview round across everyone and use the skip-levels to discuss what it found. Spradley runs one-on-one AI interviews by text or voice, with a follow-up question on each answer; invitations go by email or Slack and people answer on their own phone or computer, on any shift. Within days you get themes and the quotes behind them, compared across sites and teams, and numbers and ratings are never shown for fewer than five people, so a site manager sees what their site raised without seeing who said it. The director can ask their Personal Agent what the night shift said about handovers, get an answer that cites the quote behind each point, and have it draft a conversation guide for the next skip-level that quotes no one. Our HR and People page shows how this fits next to an existing listening calendar, and our post on employee listening strategy covers where skip-levels sit among other methods.

For individual retention conversations, the stay interview questions guide is the closer fit.

Frequently asked questions

Key terms

Skip-level meeting

A meeting between a senior manager and the people who report to that manager’s direct reports, without the manager in between present.

Skip-level report

Someone who reports to one of your direct reports.

Debrief

A follow-up conversation in which the senior manager shares themes from a skip-level with the manager in between and agrees who acts on what.

Rotational skip-level

Meeting a different group of skip-level reports each quarter when there are too many to meet everyone regularly.