Skip Level Meeting Questions to Ask Employees
Questions for a scheduled skip level meeting with someone who reports to one of your managers. Written for the leader running the meeting, with notes on what each answer tends to surface and where the conversation can go wrong.
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The questions
Each question, and why to ask it
Has anyone explained what this meeting is for, or did it just appear on your calendar?
Why ask it
Most people arrive at a first skip level quietly wondering whether they are in trouble, and asking this lets you clear that up in the first minute. If they say their manager framed it for them, you also learn something useful about that manager.
How long have you been on this team, and what were you doing before?
Why ask it
Easy to answer and it gives you the frame for everything else, since a six month employee and a six year employee are describing different companies. Watch for whether they moved internally, because internal transfers can compare teams in ways new hires cannot.
What are you actually working on this week?
Why ask it
The word actually matters, because the answer often does not match what the roadmap says they are working on. Any gap between the two is usually the most valuable thing you will learn in the half hour.
Which part of your work would you happily do more of?
Why ask it
Easier to answer than a question about strengths, and it points at the work they would take on without being pushed. If nothing on the list is anywhere near their current assignment, you have found a retention problem before it becomes one.
What is the last thing that took you far longer than it should have?
Why ask it
This gets you a concrete story rather than a general complaint about process, and the story usually names the real bottleneck: an approval, a flaky tool, a person who is a single point of failure. Ask how often that happens before you decide it matters.
When you get stuck and your manager is not around, who do you go to?
Why ask it
The names that come up are your informal experts, and they are rarely the people your org chart would predict. If the answer is nobody, this person is more isolated than their manager likely realizes.
Which meeting on your calendar could you drop tomorrow with no real consequences?
Why ask it
People will criticize a meeting far more freely than they will criticize a person, so this is a safe route into how their week is structured. If they cannot name one, either the calendar is genuinely lean or they do not yet trust you with the answer.
Is there a decision you are waiting on right now?
Why ask it
Waiting is invisible from your level, and answers here often reveal that something has been parked for weeks because nobody knew who owned it. Note the age of the wait, since that number tells you more about the organization than the decision does.
What do you think people at my level misunderstand about the work you do?
Why ask it
Framing it as a misunderstanding on your side rather than a failure on theirs gets you a much franker answer. Expect to hear about hidden maintenance work, support load, or how long something really takes, and resist explaining why the estimate exists.
Have you raised something before that never went anywhere?
Why ask it
The unanswered request is usually the reason people stop giving feedback, and finding one is more useful than collecting five new suggestions. If you hear one, say plainly whether you will pick it up or whether the answer is no.
How much of what leadership says about strategy actually reaches you?
Why ask it
Do not turn it into a quiz on the current priorities, since that shifts blame downward. What you are looking for is where the message stops: all hands, manager one on ones, or nowhere at all.
When something goes wrong here, what usually happens next?
Why ask it
This is the single best read on whether the team is safe to work in, because the answer describes actual behavior rather than stated values. Listen for whether the first move is fixing the problem or finding out whose fault it was.
Who on the team ends up helping everyone else, and does that show up anywhere in their review?
Why ask it
Glue work is systematically invisible from two levels up, and this question locates the person carrying it. If the answer is that it counts for nothing, you have both a fairness problem and a flight risk.
What is the most irritating part of your day that nobody has bothered to fix?
Why ask it
Small friction is easy to describe and easy to act on, which makes this a good source of quick wins that prove you listen. Fixing one visible annoyance buys you more candor in the next skip level than any amount of reassurance.
If you had a week with no assigned work, what would you fix or build?
Why ask it
The answers cluster around things people have wanted to fix for months, which tells you where the accumulated debt sits. Someone who cannot answer may be too buried to think past the current sprint, which is itself worth knowing.
What would you like to be doing in two years, and has anyone here asked you that?
Why ask it
The second half is the diagnostic: if nobody has asked, you have learned something about their manager without inviting a complaint. Be careful not to imply you can arrange the answer yourself, since promising a path you do not control is worse than not asking.
What would make you start looking at other jobs?
Why ask it
Asked calmly and without a follow-up about loyalty, this usually gets an honest answer, and it is far cheaper to hear now than in an exit interview. Pay attention if the reason is already partly true, because that is a live risk rather than a hypothetical.
What should I stop doing?
Why ask it
Shorter and harder than asking how you can help, because it requires them to name something specific about your behavior or your decisions. Expect a pause, do not fill it, and thank them plainly without defending yourself.
Is there anything you have held back today because you were not sure how confidential this is?
Why ask it
This gives them a second chance near the end, once they have seen how you handled the earlier answers. Whatever you promise here, keep exactly, because a single traced comment ends candid skip levels for the whole team.
What do you want to ask me, including anything you think I might dodge?
Why ask it
Naming the dodge invites the question they actually care about, usually about reorgs, headcount, or whether a project is being cancelled. Say what you cannot discuss and why rather than pretending you do not know.
Where does your work come from, and how often does it change after you have started?
Why ask it
Frequent mid flight changes usually point to a planning problem upstream rather than indecision on the team. If work arrives from four different directions, you have found a prioritization gap that no individual can solve on their own.
How do you know whether you did a good job last month?
Why ask it
If the only answer is that nobody complained, the team is operating without feedback and people are guessing at what counts. Employees who can name a specific measure usually feel steadier, whether or not the measure is a good one.
How much of your week goes to redoing work that was already done once?
Why ask it
Rework is usually the single largest hidden cost in a team and the one nobody is tracking. Ask for the cause of the most recent instance, because unclear requirements, late reviews, and shifting scope each need a different fix.
Which handoff between teams breaks most often?
Why ask it
Naming the handoff rather than the team keeps the answer from becoming a complaint about people, which means you get a straighter one. Ask what usually happens when it breaks, since the recovery cost is what justifies changing the process.
When a customer complaint comes in, how far does it travel before someone can act on it?
Why ask it
The number of hops is a good measure of how responsive the organization really is, as opposed to how responsive it says it is. If the answer includes a stage where things sit and wait, you have found the queue worth attacking.
Which of your tools or systems do you fight with most?
Why ask it
Complaints about software are safe to voice, so this gets people talking before harder questions arrive. Ask how much time the fight costs per week, since that number is what turns a familiar gripe into a fundable fix.
What do you get asked to do that is not really your job?
Why ask it
Some of this is healthy flexibility and some of it is a role that has quietly become two roles, and the distinction matters for both workload and pay. Listen for whether the extra work is occasional or now permanent and unacknowledged.
Who is affected if you are out sick for a week?
Why ask it
This maps the real dependencies faster than any documentation exercise, and it identifies single points of failure without asking anyone to admit to being one. If the answer is everything stops, that is a risk to fix, not a compliment to pass along.
What do new people on your team struggle with in their first month?
Why ask it
People answer freely because the problem belongs to onboarding rather than to them, and the answers point at undocumented knowledge. If several people name the same thing, you have a cheap, concrete improvement waiting.
Is there a rule here that people quietly work around?
Why ask it
Workarounds are evidence that a policy does not fit the job, and the people doing the work know about them long before leadership does. Respond with curiosity rather than enforcement, or you will never hear about another one.
When did you last tell someone that their idea would not work, and how did that go?
Why ask it
The story tells you whether disagreement is survivable on this team, which no direct question about safety will reliably answer. If they cannot recall ever doing it, ask whether that is because they agree with everything or because it is not worth the trouble.
What does your team do that customers never see?
Why ask it
Invisible work is what gets cut by accident during reorganizations and what gets left out of headcount arguments. Expect answers about maintenance, support rotations, and cleanup, and note how much of the week it consumes.
What is the last good result of yours that nobody outside the team heard about?
Why ask it
This finds work worth amplifying and tells you whether recognition is reaching upward at all. If the team has a pattern of quiet wins, the fix belongs to you and their manager rather than to them.
What would you warn a friend about before they took a job on this team?
Why ask it
The friend framing makes honesty easier than asking about their own satisfaction, and the warning is usually accurate. Take the answer as information about the job rather than as disloyalty, and thank them for it plainly.
What should I be asking in these conversations that I am not?
Why ask it
It hands over the agenda at the end, when they know what you did and did not cover, and the answers usually name a topic you have been avoiding. Use what you hear to change the questions for the next set of conversations.
Running a Skip Level Without Undermining the Manager
Practical guidance for the conversation itself
Before and During the Meeting
Tell the manager first
Let the direct manager know the meeting is happening and why, before the invitation goes out. A manager who finds out afterwards will reasonably assume they are being audited, and the next thing they do is coach their team on what to say.
Say what happens to what you hear
In the first two minutes, state your rule: themes get shared, names and quotes do not, unless they ask you to raise something directly. Then hold to it. Vague promises of confidentiality are worse than a clear boundary, because people test them.
Do not solve anything in the room
Fixing a problem directly in someone else's org routes future problems around their manager and creates a shadow escalation path. Take the item, hand it to the manager with context, and tell the employee that is what you are doing.
Expect the first one to be polite
A first skip level usually yields upbeat, careful answers. The useful ones are the second and third, once the person has seen that nothing bad happened. Judge the practice on a cadence of two or three meetings a year per person, not on one conversation.
Close the loop within two weeks
Come back with one thing you changed, one thing you asked the manager to look at, and one thing you are not going to do and why. The no matters as much as the yes; it is what convinces people you were actually listening rather than collecting.
What Goes Wrong
Asking outright how their manager is doing
Almost nobody answers honestly, and the question itself signals that you suspect something. You learn more from asking who they go to when stuck, whether anyone has asked about their two year plan, and what happens after a mistake.
Letting it drift into a performance conversation
If you start giving feedback on their work, the meeting becomes a review with no manager present, and they will never speak freely in one again. Keep your input on systems, priorities, and things you own.
Taking one person's account as the state of the team
Two levels down, you are hearing one vantage point shaped by one manager relationship and one project. Wait for the same complaint from three unconnected people before you act on it as a pattern.
Promising things outside your control
Titles, transfers, and headcount all involve other people. Say what you will advocate for and what the actual decision process is, then let the employee judge the odds for themselves.
Running it like a survey
35 questions in thirty minutes produces twenty shallow answers. Pick four, follow each one down two levels of detail, and leave the rest for next time.