Skip level meeting questions that get honest answers

The best skip-level meeting questions are open, tied to the work, and easy to answer honestly in front of someone senior. Ask what is slowing the team down, what they would change if they ran the team for a week, what their manager does that helps most, and what leadership probably isn't hearing. Leave out status updates and anything that sounds like you are building a case against their manager. Below are 18 questions grouped by topic, a 30-minute agenda, a time budget for a 40-person company, and a follow-up checklist.

What is a skip-level meeting?

A skip-level meeting is a conversation between a senior leader and someone who reports to one of that leader's managers. The leader "skips" the level in between. At a 20- to 300-person company, that usually means the founder, CEO, or COO sitting down with people who report to a team lead.

Keep it separate from performance reviews and investigations, and never use it to go around the manager. You want to hear how the work feels from the inside, in the employee's own words, without it being summarized for you first.

Why do skip-level meetings matter on a small team?

Because feedback loses detail every layer it travels up. I call this the manager filter.

It usually goes like this. An engineer tells their lead the release date is unrealistic. The lead tells the head of product the timeline is tight. By the time it reaches the founder, it sounds like "a few risks, but we're on it." Nobody lied. Each layer just took a little edge off, usually to protect someone or to avoid sounding negative.

Research backs up how common that silence is. In a study of 40 full-time employees, Milliken, Morrison, and Hewlin found that 85% had at least one time when they felt unable to raise an important concern with their boss. The most common reason was fear of being seen or labeled negatively, followed by fear of damaging a relationship and a sense that speaking up would not change anything.

Gallup estimates that managers account for at least 70% of the variance in employee engagement scores across business units. If you only hear about a team through its manager, you are hearing about the team through the single biggest influence on how that team feels.

Small companies feel this faster. On a team of six, one person's slide toward quitting barely moves an average score, and the manager may be the last to say it out loud. A skip-level meeting is one of the few places you hear it directly. If you are already seeing the quiet version of this, read what to do when employees stop speaking up.

What questions should you ask in a skip level meeting?

Pick five or six of these, not all 18. A meeting where you read a list feels like a survey with eye contact.

Opening questions

1. What has been the best part of your work in the last month?
2. Which project do you wish more people knew about?

Questions about the work

1. What is slowing you down right now?
2. If you ran this team for a week, what is the first thing you would change?
3. Are you waiting on a decision from someone above you?
4. Which process would you delete tomorrow if you could?

Questions about the team

1. How is the workload spread across the team right now?
2. Who on the team deserves more credit than they get?
3. When the team disagrees, how does it usually get settled?

Questions about support from their manager

1. What does your manager do that helps you most?
2. How could I help your manager help you?
3. Do you get enough feedback to know how you are doing?

The feedback question is more important than it looks. In Gallup's 2024 data, only 23% of US employees strongly agreed they had received meaningful feedback in the past week.

Questions about growth and staying

1. Where would you like your work to be a year from now?
2. What is working well right now that you wish we did twice as much of?
3. Which skill do you want to use more that you don't get to use here?

If you want a deeper set on retention, the stay interview questions for managers post goes further.

Questions about the company

1. What about where the company is going doesn't make sense to you?
2. Is there something people say about leadership that we probably aren't hearing?

Closing question

1. What should I have asked that I did not?

What should you not ask in a skip-level meeting?

A few questions reliably shut people down or put them in a bad spot.

• "How is your manager doing?" This turns the employee into a judge of their boss. Ask about support instead, using the manager questions above.
• "Is anyone on the team not pulling their weight?" You are asking them to report on a peer. Expect a polite non-answer and a worried team afterward.
• "Are you happy here?" It is a yes or no question, and almost everyone says yes to a founder.
• Status questions like "Where are we on the launch?" That belongs in a team meeting.
• Anything about job security you cannot answer honestly. If you can't speak to layoffs or reorgs, don't open the topic.

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

Tell the manager first, and tell them the real purpose. Something like "I'm meeting everyone on your team this quarter to hear how the work feels. I'll share themes with you, not names, and I won't make decisions about your team in those rooms." Managers get nervous about skip levels when they hear about them from their team.

Then hold yourself to one rule. You listen and take notes in the meeting. You do not fix, promise, or overrule. Anything that needs to change goes back through the manager. The exception is anything involving harassment, safety, or the law, which you act on directly.

Here is a 30-minute agenda you can copy.

• 0 to 5 minutes. Say why you are meeting, that this is not a review, and what happens to your notes.
• 5 to 20 minutes. Ask five or six questions from the list above. Follow up with "Tell me more about that" more than with new questions.
• 20 to 27 minutes. Their questions for you. Answer plainly, and say "I don't know yet" when that's true.
• 27 to 30 minutes. Repeat back the two or three things you heard and say when they will hear from you.

On small teams, be careful with anonymity. If one person on a team of four raises a concern, "someone on your team said" is not anonymous. Wait until you hear a theme from more than one person, or raise it as your own observation. The guide on how to anonymize employee feedback on a small team covers the rules in more detail.

How often should you hold skip-level meetings?

Once a quarter per person is a good default for companies under about 60 people. Above that, switch to small groups. Here is the time math for a founder.

Worked example at 40 people. Say you have 4 managers and 36 people who report to them. Each skip level is 30 minutes plus 10 minutes to write up notes, so 40 minutes per person.

• 36 people × 40 minutes = 1,440 minutes, or 24 hours per quarter.
• A quarter is 13 weeks, so that is a little under 2 hours a week.
• Twice a year instead of quarterly cuts it to under 1 hour a week.

Worked example at 120 people. Say 100 people sit below a manager. One-on-ones would take about 67 hours a quarter, around 5 hours a week. Groups of 4 change the math. That is 25 sessions of 45 minutes plus 15 minutes of notes, so 25 hours a quarter, again under 2 hours a week.

Groups get you less depth on any one person, so pair them with something that reaches everyone. A short anonymous employee engagement survey tells you which teams to visit first, and the skip levels tell you why the numbers look the way they do.

What do you do after a skip-level meeting?

The follow-up is where trust is built or lost. If people talk and nothing happens, the next round will be shorter and more polite. Use this checklist.

• Within 24 hours, write down themes, not quotes, and leave out names where you can.
• By the end of the week, send the employee a short note covering what you heard, what you will do about it, and what you will not do and why.
• In your next one-on-one with the manager, share the themes and agree on one change, not five.
• When the same theme comes from three or more people, treat it as a team or process issue before you look at any one person.
• Open the next skip level by saying what changed since last time.

If you are not sure whether what you heard is a one-off or a pattern, how to know if your team is unhappy before someone resigns walks through the early warning signs.

If you want help setting up skip levels, or someone outside the company to run the first round so people speak more freely, Book a Strategy Call.

FAQ

What is the purpose of a skip-level meeting?

To hear directly from people one level below your managers about how the work, the team, and the company feel to them. It fills the gap left when feedback gets softened on its way up.

Should the manager know about a skip-level meeting?

Yes. Tell the manager before the invite goes out, explain the purpose, and promise to share themes rather than names. Surprise skip levels make managers defensive and employees cautious.

How long should a skip-level meeting be?

Thirty minutes is enough for a one-on-one. Group sessions of three or four people work better at 45 minutes so everyone gets time to talk.

Are skip-level meetings confidential?

They should be, with clear limits. Tell people you will share themes without names, and that anything involving harassment, safety, or the law is the exception you have to act on.

Sources

• An exploratory study of employee silence. Issues that employees don't communicate upward and why. Milliken, Morrison and Hewlin, Journal of Management Studies, 2003.
• Managers Account for 70% of Variance in Employee Engagement. Randall Beck and Jim Harter, Gallup, 2015.
• U.S. Employee Engagement Inches Up Slightly After 11-Year Low. Jim Harter, Gallup, 2024.