Questions to Ask in a Skip Level Meeting
Questions for a half hour with your manager's manager: what to ask, what to leave with your own manager, and how to use the time when you have no agenda of your own.
The questions
Open any question for the note
What made you set these up, and what are you hoping to get out of them?
Why ask it
Leaders who arranged skip levels themselves can usually name something specific they want to learn. If the answer is that HR asked them to, keep your feedback modest this round and spend the time listening instead.
How much do you already know about what my team works on day to day?
Why ask it
Saves the most common waste in these meetings: twenty minutes of background they did not need, or a critique they cannot follow. Their answer sets how much context the rest of the conversation requires.
What does our team look like from where you sit? What reaches you, and what doesn't?
Why ask it
Tells you which of your team's work is visible upward and which is invisible. Invisible work is the work that gets cut first, and this is the cheapest way to find out you have some.
What do you look at first when you are trying to tell whether a team is healthy?
Why ask it
Listen for whether they name people, dates, or dashboards. That is the lens they will use at review time, and it is often not the one your own manager uses.
Looking at the next two quarters, which part worries you?
Why ask it
Worry is more informative than priorities. Priorities get published; the thing keeping a senior leader awake usually does not, and it tends to be where budget and attention move next.
If the budget halved, which of our current projects would you protect?
Why ask it
Forces a ranking instead of the usual answer that everything matters. If they cannot rank, nobody above you has done the work of choosing yet, which is worth knowing before you plan next quarter.
Is there anything my team does that you would be fine with us stopping?
Why ask it
A leader who can name something to drop is giving you permission you cannot get anywhere else. Silence here means the work will keep accumulating and you should stop waiting for someone to call it off.
What do you wish reached you faster from teams like mine?
Why ask it
Points at a reporting gap you may be able to close with almost no effort. It also lands as an offer of help rather than a complaint, which makes the rest of the meeting easier.
Where do you think we are slower than we should be, and do you know why?
Why ask it
Asks for a diagnosis rather than a gripe. If they blame one team, be careful with what you say next. If they describe a handoff or an approval step, you have something concrete you can go and fix.
Is there a recent decision you think people at my level misread?
Why ask it
Gets the reasoning that did not survive the all-hands slide. It also shows you how candid this person is willing to be with someone two levels down, which sets the ceiling for everything else you ask.
How do you decide what to say no to?
Why ask it
Most leaders can describe their declines honestly, and the pattern tells you how to frame a proposal so it is not the thing that gets turned down. Vague answers here often mean the pipeline is not being managed.
What has changed in how you see the business over the last six months?
Why ask it
Someone whose view has not moved at all is either steady or not paying attention, and the detail tells you which. It is also an indirect way to hear which numbers they actually trust.
Which decisions do you expect people at my level to make without checking?
Why ask it
The gap between what you think you may decide and what they expect you to decide is where most escalation friction lives. Naming the boundary out loud is the whole value of asking.
How do promotions in my discipline really get decided, and who is in the room?
Why ask it
Written criteria and actual decisions rarely match. This is one of the few chances to hear who argues your case when you are not there and what evidence they are expected to bring.
As far as you are able to say, how are the company's finances?
Why ask it
The limit is built into the question, so they can answer without breaching anything. What they decline to say, and how quickly they decline, is often the more useful half of the answer.
Have you heard anything about how our team works that you'd like me to confirm or push back on?
Why ask it
Gives them a safe way to check a secondhand impression with someone closer to the work, and gives you a chance to correct it before it hardens into a decision about headcount or scope.
If I bring you a problem you can't fix, what do you want me to do with it?
Why ask it
Heads off the usual outcome where you raise something, nothing happens, and both sides feel let down. You want to know whether they expect escalation, documentation, or patience.
What did you get wrong early in your career that you'd warn me about?
Why ask it
Career questions in the abstract produce platitudes. Asking for a specific mistake gets a story, and the mistakes senior people admit to are often ones the organization still quietly rewards.
If you were sitting in my seat, what would you want to know?
Why ask it
Hands them the agenda. Leaders who have done a job like yours recently name something concrete; ones who have not will change the subject, which tells you how much of your reality they hold.
What would make this half hour worth your time?
Why ask it
Surfaces the thing they came for and did not get to, usually in the last two minutes. It also gives you a reason to ask for a second meeting that is not just about you.
Using a skip level well
Practical guidance for the conversation itself
Before you go in
Bring one thing, not five
A skip level is usually twenty five minutes of real conversation. Pick one observation you want to land and one thing you want to learn. Trying to cover a list means neither of you remembers anything afterwards.
Tell your own manager it is happening
Not to ask permission, but so they hear it from you first. Skip levels go wrong most often when a manager finds out secondhand and reads it as going around them.
Decide what this meeting is not for
It is not the place to negotiate pay, appeal a review, or route around a decision your manager already made. Raising any of those costs you more standing than the answer is worth.
How to raise something difficult
- Describe what you saw before you say what it means: dates, handoffs, how long something waited.
- Say whether you have already raised it with your manager. If you have not, expect to be sent back, and that is reasonable.
- Ask for a decision or for information, not for sympathy. Naming which one you want stops the conversation drifting.
- If the honest answer to why you are raising it is that you are frustrated, say so plainly and briefly rather than dressing it up as strategy.
- Leave silence after you finish. Senior people often need a beat, and filling it usually softens the point you just made.
What goes wrong
Turning it into a performance
Questions designed to show how strategic you are read as exactly that. A specific question about the work you actually do lands better than a broad one about industry direction.
Complaining about your manager
It rarely produces a change and almost always gets relayed. The exception is conduct that involves safety, harassment, or dishonesty, and that belongs with HR or a formal channel rather than a chat over coffee.
Asking only about yourself
Promotion and growth questions are fair, but if every question is about your path, the leader learns nothing about the team and you lose the chance to hear how the business actually works.
Afterwards
- 1Send four or five lines the same day: what you took away, and anything you said you would follow up on.
- 2Tell your manager what you discussed, in one paragraph, without making them ask.
- 3Do the one small thing you offered. Following through on a minor promise is what makes the next skip level useful.
- 4Write down anything they said about priorities or finances, and check it against what happens over the next quarter.