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Skip level meeting questions: what to ask, from either side of the table

A skip level meeting is a one-on-one between someone and their manager's manager. The best questions are open, about the person's own experience, and never put them in the position of reviewing their boss: "What's one thing that would make your work easier?" beats "Is your manager any good?" Pick five questions for a 30-minute meeting, not thirty, and send a short note afterwards saying what you'll do with what you heard.

As a new manager you may be on any side of one. Your own boss's boss may book one with you. Your boss may hold them with your team. Or you may lead a team lead and hold them yourself. This guide covers all three: questions for each, a 30-minute agenda, the opening words, what not to ask, and what to do afterwards.

What a skip level meeting is for

A skip level meeting lets a senior manager hear directly from people two levels down, without the middle manager in the room. Done well, it does three things:

• It tells the senior manager what's really happening day to day, which reports don't.
• It gives the employee a direct line to someone who sees more of the company.
• It surfaces problems early: workload, unclear priorities, blockers between teams.

It is not a performance review of the middle manager, a status update, or a way around them. If it turns into any of those, people stop speaking openly within a round or two.

Pick five questions, not thirty

Most lists hand you 30 to 100 questions. In 30 minutes, you'll get through five or six well, and the real value is in the follow-up questions ("Tell me more about that"). A good set covers one question from each of these:

1. Warm-up: "What are you working on right now that you're enjoying?"
2. The work: "What's one thing that slows you down most weeks?"
3. The team: "How would you describe how the team works together right now?"
4. Support: "What could your manager or I do that would help you most?"
5. Growth: "Where would you like to be in a year or two?"
6. Close: "Is there anything I didn't ask that I should have?"

That's the default set. Swap one or two for the questions below when there's a reason: a reorganisation, a new manager on the team, a project that went wrong.

Skip level meeting questions to ask employees

For when you're the senior manager meeting someone on a team you lead through another manager.

To start

• "What's been the best part of your last month at work?"
• "What does a normal week look like for you right now?"
• "What's something you're proud of that I might not know about?"

About the work

• "What's one thing that gets in the way of doing your best work?"
• "If you could change one process tomorrow, what would it be?"
• "Is there anything we do that you think we should stop?"
• "Do you know what the team's top priority is this quarter? How does your work connect to it?"
• "Which other team is hardest to work with, and why?"

About the team

• "How does the team make decisions? Does it work?"
• "When there's a disagreement on the team, what usually happens?"
• "Who on the team helps others most, in ways that might not show?"
• "What would make this a better team to be on?"

About support and their manager (asked safely)

• "What's one thing your manager does that really helps you?"
• "What support would you like more of, from your manager or from me?"
• "Do you get the feedback you need to know how you're doing?"
• "Do you have what you need to grow here?"

Notice these ask about the support someone gets, not whether their manager is good. You'll still hear about the manager. You just won't be asking someone to judge their boss to their boss's boss, which most people won't do honestly.

About growth

• "What skill would you most like to build this year?"
• "Is there a project or area you'd like to be part of?"
• "What would make you want to stay here for the next two years?"

About the company

• "Is there a company decision that's been confusing? I'll try to explain it."
• "What do you hear people on the team worrying about?"
• "If you were in my seat, what's the first thing you'd change?"

To close

• "What's one thing you'd like me to take away from today?"
• "Is there anything I didn't ask that I should have?"
• "Is there anything you'd like me not to share, even as a theme?"

Skip level meeting questions to ask your boss's boss

When you're the one invited, as a new manager or a team member, come with three or four of your own questions. It's the best chance you'll get to understand what senior people care about, and to be seen as someone who thinks beyond their own task list.

About direction

• "What are the two or three things that matter most for the business this year?"
• "How does our team's work fit into that?"
• "What would you like our team to be known for a year from now?"
• "What's the biggest risk you see for our area?"

About how you're doing

• "From where you sit, what does our team do well? Where could we be better?"
• "What does a great manager look like at this level here?"
• "Is there anything you'd like me to do more of, or differently?"

About growth

• "What skills do you think matter most for someone in my role to move up here?"
• "What do you wish you'd known when you first became a manager?"
• "Is there a project where you think I could help?"

What to bring up yourself

Raise one blocker you can't solve at your level, framed as a question with a suggestion: "Our handoffs with the warehouse team are slowing orders by about a day. I've talked to their lead; we think a shared tracker would fix it, but it needs budget. Would you support that?" Senior managers remember people who bring a problem and a fix.

What not to do

• Complain about your direct manager. If there's a serious issue, raise it with them first, or with HR.
• Bring a list of small grievances. Pick one thing.
• Pretend everything is perfect. They'll know it isn't.

When your boss holds skip levels with your team

This is the one most new managers worry about. Your manager is going to sit with your people without you. It's normal, it's usually good for you, and there are a few things you can do to make it go well.

• Ask to hear about it in advance. "Will you let me know before you book them, so I can tell the team what they're for?"
• Tell the team yourself. "Dana's going to have a skip level with each of you this month. It's a normal thing; she wants to hear how things are going from you directly. Be as open as you like, including about me."
• Don't ask your team what they said. Not before, not after. It undoes the whole point.
• Ask your boss for themes, not names: "Was there anything you heard that I should work on?"
• Act on one thing and say so. "A few of you said priorities change too often. From now on, I'll only change the weekly plan on Mondays."

If feedback comes back that stings, treat it as you'd want your team to treat yours: thank your boss, ask for a specific example if you can have one, and change one thing.

Want words like these ready every morning? Take the 2-minute quiz and get a 10-minute lesson and one script a day, for meetings like your skip-level.

A 30-minute skip level agenda

The opening words

"Thanks for making time. I do these with everyone on Sam's team every few months. It's not a review of you or of Sam; I just want to hear how things are going from you directly. I'll take a few notes. I'll share themes with Sam, things like 'people would like clearer priorities', but not who said what, unless you tell me something about safety or conduct that I have to act on. Sound OK?"

Saying the confidentiality rule out loud, including its limit, is what gets people talking. Don't promise total secrecy; you can't keep it if someone reports harassment.

On a small team: when "themes, not names" won't work

With three people, "someone said priorities are unclear" points at someone. On a small team:

• Tell people up front that themes may be recognisable, and ask them to tell you what they'd rather you didn't pass on.
• Combine what you hear with other sources (a team meeting, a survey) before sharing it.
• Wait for two rounds before sharing a theme that only one person raised.
• Or hold a group skip level instead: the senior manager with the whole team, no middle manager, asking the same questions.

Questions to avoid

After the meeting: notes, follow-up and the middle manager

A skip level that leads to nothing is worse than none: it teaches people that speaking up is pointless.

1. Write notes within the hour. What they said, in their words, and anything you promised.
2. Send a short thank-you the same day, with any promise you made: "Thanks for today. I'll find out why the approval takes two weeks and come back to you by the 20th."
3. Collect themes after you've met several people. One person's comment is a data point; three saying the same thing is a pattern.
4. Share themes with the middle manager in your next 1:1 with them, framed as help, not a verdict: "Several people said priorities shift mid-week. What do you think is behind that?"
5. Close the loop with the team within a month: what you heard, and what's changing. "Several of you raised the approval delay. It's now three days, not ten."
6. Act on serious issues at once. Harassment, safety, or anything illegal goes to HR the same day, not into a themes list.

How often to hold skip level meetings

For most teams, once a quarter or twice a year with each person is enough. More often, and it can start to feel like checking up on the middle manager; less often, and nobody remembers the last one. Hold them more often during big changes: a new manager on the team, a reorganisation, a hard quarter. If you have dozens of people two levels down, rotate: a few each month, so everyone gets one in the year, and use group skip levels to fill the gaps.

Skip levels don't replace regular 1:1s between each person and their own manager. If those aren't happening, start there; our guides on how to have an effective 1 on 1 and one on one questions to ask employees cover them.

How you handle hearing about yourself from someone else's meeting says a lot about your style. The free leadership style quiz takes about 2 minutes and names yours, with the conversations it tends to put off.

Questions about skip level meetings

What is the purpose of a skip level meeting?

To let a senior manager hear directly from people two levels down, and give those people a direct line upward. It surfaces blockers and ideas that don't travel well through reports.

How should I prepare for a skip level meeting as an employee?

Bring three or four questions about direction and growth, one blocker with a suggested fix, and something you're proud of. Don't bring a list of complaints about your manager.

Should my manager know what I say in a skip level meeting?

Usually they'll hear themes, not your words. Ask at the start: "What do you share afterwards?" If something must stay private, say so.

Is a skip level meeting a bad sign?

No. Most are routine, booked with everyone on a team. If you're the only one, it's fair to ask your manager what it's for.

How long should a skip level meeting be?

30 minutes is standard. 45 to 60 works for a first one, or when there's a lot to cover, such as after a reorganisation.

Can skip level meetings be done in groups?

Yes. A group skip level (the senior manager with a whole team, no middle manager) works well for large teams or small ones where individual comments would be easy to trace.

Next: take the free leadership style quiz to see what kind of new manager you are, or browse all our guides for new managers.

Sources

• Lattice, "30+ Skip Level Meeting Questions for Senior Leaders": https://lattice.com/articles/skip-level-meeting-questions
• Windmill, "Skip-Level Meeting Questions: 30 Examples": https://gowindmill.com/resources/lists/skip-level-meeting-questions/
• U.S. Equal Employment Opportunity Commission, "Harassment": https://www.eeoc.gov/harassment