By Andreas Pettersson, Founder, Leaders ADAPT
Most lists of skip-level meeting questions have sixty or seventy entries and open with "what's your favorite book?" I understand why. The person writing the list has never sat across from an engineer two levels down who has thirty minutes, a manager they like, and no reason on earth to tell the CEO anything risky.
You do not need seventy questions. You need about four, asked in an order that earns the fourth, and you need to know what the answers mean. This page gives you that, for the leader and for the employee, with the answers to listen for.
Quick answer: The four skip-level meeting questions that do the work, in order, are what is working well, what is frustrating you right now, what one thing you would change about how we work, and whether there is anything you are not comfortable telling your manager. Open by saying what the meeting is not, ask each one and stay silent, and thank the person before you react to anything unwelcome.
Order the questions so people open up: why sequence beats the list
A skip-level meeting question is a question a leader asks an employee two levels down, chosen to surface what the layer in between softens or drops. The word that matters in that definition is surface. You are not collecting opinions. You are trying to get past a filter.
The filter exists because your reactions carry about ten times the weight you feel them at. People two levels down, your direct reports' direct reports, have learned that speaking up to you costs something and staying quiet costs nothing.
So the question that matters most, the one about what they cannot tell their manager, is useless as an opener. Nobody answers it cold. It works at minute twenty, after three easier answers were received well.
I run the same discipline in my own rooms. Before any content, everyone puts a number on the table: energy today, one to ten. It is not the number that matters. Forcing yourself to put down a number identifies the gap, and it gives the other person a first easy answer that was received without judgment.
That is the whole trick of sequencing: a run of small honest answers that cost nothing, so the expensive one becomes possible.
The four core skip-level meeting questions, in order
These are the four I published in The 5-Minute Leader, and they have not changed.
- What is working well? Start here so the person can be honest without being negative. Listen for specifics. "The team's great" is a polite answer; "the new release checklist cut our Friday fires" is information.
- What is frustrating you right now? Not "any problems?", which invites "no." Frustration is a lower bar than problem and people will step over it.
- If you could change one thing about how we work, what would it be? One thing forces a ranking. It also shows you what they think is in your power to change, which is its own data.
- Is there anything you are not comfortable telling your manager? Last, and only after the first three landed well. With indirect communicators, ask it as a door rather than a spotlight: "What would you want your manager to know that is hard to say in a one-on-one?"
Before question one, the sentence that makes all four possible: "This isn't about your manager. I want to understand your experience directly."
Three follow-up areas when you have time
If the four questions land and there is time left, three areas are worth a second question each. Pick one area per meeting, not all three.
Ownership and authority
What do you own right now? What decisions can you make without checking with anyone? When did you last make a call without asking your manager first? These three come from the delegation checks in The 5-Minute Leader, and they tell you whether authority actually moved down the chart or whether your managers are carrying every decision back up to themselves.
The uncomfortable ones
From the bank I keep for one-on-ones, the two that translate best to a skip-level: "What are we not talking about that we should be?" and "If you ran this company, what would you change first?" The second one is the best strategic question I know for someone two levels down. They see the machine from underneath, and they will tell you which part grinds.
Career and energy
"What are you not getting here that you need?" and "Where are you phoning it in?" Ask these only when trust is already there. They are the kind of question a good direct manager should be asking, so their real value in a skip-level is finding out whether anyone ever has.
Questions and answers: what good and bad answers sound like
A list without the answers is a form. Here is what a healthy answer and a worrying answer sound like for each core question.
| Question | A healthy answer sounds like | A worrying answer sounds like |
|---|---|---|
| What is working well? | A specific process, decision or person, with a reason | "Everything's fine", or a compliment about you |
| What is frustrating you right now? | A concrete blocker, with what they have already tried | "Nothing really", or something they have never raised with their manager |
| What would you change? | One thing, ranked, with a rough idea of how | A list of five, or "not sure that's my place" |
| Anything you can't tell your manager? | "No, and here's why I trust her", or a real item raised carefully | A long pause and then "no", or a complaint about a person that skips the problem |
Two patterns to read across meetings rather than inside one. First, the tripwire from The 5-Minute Leader: three skip-levels in a row saying "I don't really know what I own" or "my one-on-ones are just status updates" is a management problem, not three people problems.
Second, energy over time. Someone whose energy reads seven, then six, then six, then five across a year of quarterly conversations is sliding toward the exit, and no single meeting would have shown you that. If you are not writing the numbers down, you are not seeing the pattern.
Healthy signals of the whole practice, from the trust work I publish: over a year, people ask you fewer permission questions, information arrives earlier, disagreement increases, and energy scores rise. If the numbers go the other way, the meetings are being held but the filter is winning.
How to receive an answer you do not like
The two seconds after an unwelcome answer are the entire game. What your face does, what your first word is, and whether you defend yourself or get curious.
Three rules. Thank them before you evaluate; "thank you for telling me that" is a complete sentence. Ask one more question before you explain anything. And never, in any room, punish the person who carried the message, because shooting a messenger once in public re-chains the whole company.
In the company I ran, the person who raised the flag on a problem was celebrated for it, even when the problem was theirs, because they named it and told everyone how to avoid it next time. That recognition, given in the room, is the culture the questions depend on. Feedback only flows upward where it has been safe to send.
What not to ask in a skip-level meeting
Four kinds of question that wreck the meeting.
Anything that audits the manager by name. "How is Sarah doing as a manager?" turns the employee into an informant and they know it. Ask about the work and the team; the manager will show up in the answers if they need to.
Anything you could have read. Status, deadlines, the number. If a skip-level becomes a status update, you have taught the person that this is what you value hearing.
Anything performative. The favorite-book icebreakers are fine over lunch. In a thirty-minute skip-level they spend the minutes you needed for question four.
Anything you will not act on. If you ask what they would change and then change nothing, next quarter's answer will be shorter.
What to ask as the employee
If you are the person two levels down, the meeting is also yours. Come with two or three questions, not ten. The ones that read as an owner rather than a job seeker:
- Which part of this year's strategy do you think our team understands least?
- From your seat, what separates good from great in a role like mine?
- What worries you most about our part of the business over the next two quarters?
- Is there a problem you would hand to someone on our team if they asked for it?
Skip "how am I doing", which puts your manager on the spot in your absence, and skip anything you have not first raised with your own manager. The full preparation, including how to raise a concern without it reading as going over your manager's head, is on how to prepare for a skip-level meeting as an employee.
Should you send a skip-level meeting questionnaire in advance?
Send the topics, not a form. A written questionnaire produces written answers, and written answers to a CEO are edited for safety before they are sent. What works is an invitation that names the four areas you will ask about, so nobody is ambushed, and a conversation where the answers are spoken. The skip-level meeting template page has the invitation email that does this, plus the agenda by minute and the note you send the manager afterwards.
The exception is scale. If you run skip-levels with hundreds of people, a short written pulse between conversations is fine, as long as the conversation still happens and the form never replaces it.
How these differ from one-on-one meeting questions
In your own one-on-ones you have earned depth over months, so you can reach for the shadow-side prompts early. In a skip-level you have not, so you start lighter, and the prompts about what someone tolerates work especially well because skip-levels surface standards problems managers absorb silently. The full bank for the manager's own meeting is on one-on-one meeting questions; the purpose, cadence and what to do with what you hear is on the skip-level meetings guide.
Skip-level meeting questions: the FAQ
What should a leader ask in a skip-level meeting?
Four prompts in sequence do most of the work: what is working well, what is frustrating you right now, what one thing would you change about how we work, and is there anything you are not comfortable telling your manager. Ask them in that order so the earlier, safer answers build the trust the last question needs. Add one follow-up area per meeting, such as ownership and authority or career and energy, when time allows.
What are good discussion points for a skip-level meeting?
Good discussion points are the work itself, the team's blockers, how decisions get made, what the employee owns, their career direction, and what they would change about how the company operates. Weak discussion points are status updates the leader could have read, anything that audits the direct manager by name, and icebreakers that use up a thirty-minute meeting. Each point should produce something the leader can act on or pass back to the manager as a theme.
What are five good things to ask if you only have a few minutes?
What is working well? What is frustrating you right now? If you could change one thing about how we work, what would it be? What do you own right now, and what decisions can you make without asking? Is there anything you are not comfortable telling your manager? Asked in that order, five prompts fit comfortably into fifteen minutes if the leader stays quiet after each one and takes notes rather than responding.
What should an employee ask in a skip-level meeting?
Employees get the most from two or three prompts about direction and expectations: what the leader wishes the team understood about this year's priorities, what great looks like in the employee's role from the leader's seat, what risk the leader sees for the team in the next six months, and whether there is something the employee could take on that would help. Anything about the direct manager, or about promotion timing, is better raised elsewhere.
What should you not ask in a skip-level meeting?
Avoid anything that evaluates the direct manager by name, because it turns the employee into an informant and damages trust in both directions. Avoid status and deadline checks the leader could have read in a report. Avoid performative icebreakers that consume the time needed for harder prompts. And avoid asking about anything the leader does not intend to act on, since unanswered suggestions teach employees to give shorter answers next time.
Should a skip-level meeting questionnaire be sent in advance?
Send the topics, not a questionnaire. Telling the employee in the invitation that the conversation will cover what is working, what is frustrating, what they would change, and anything hard to raise with their manager prevents an ambush without producing pre-edited written answers. A written form is a reasonable supplement at large scale, but written responses to a senior leader are usually edited for safety and should not replace the spoken conversation.
The one question I would keep
If the calendar only left me one question for someone two levels down, it would be the third: if you could change one thing about how we work, what would it be? It ranks their frustrations for you, it tells you what they believe is in your power, and it hands you something to act on before the next meeting, which is the only proof that the meeting was real.
Listen for the pause before they answer. A short pause means they have thought about it and were waiting to be asked. A long one means nobody has asked in a while, and that pause is the most useful skip-level meeting answer you will get without asking.
Where the four prompts come from
They are one page of The 5-Minute Leader, the system I wrote for leaders who have no spare hour: a one-on-one protocol built on the same sequencing, the delegation checks behind the ownership prompts above, and a scaling section for anyone who now manages managers. If your skip-levels keep producing "everything's fine", the fix is usually upstream in how your managers run their own one-on-ones, and that is where the book starts.
Andreas Pettersson wrote The 5-Minute Leader after a decade as a tech CEO, including years as one of Canon's youngest CEOs at an AI company that grew past 150 people. He founded Leaders ADAPT.
