Questions to Ask at Skip Level Meeting
Questions for a thirty-minute conversation with your manager's manager: what they are working on, how your team looks from a level up, what strong work looks like from there, and how to bring them something useful.
The questions
Open any question for the note
What are you focused on this quarter that we probably do not see from where we sit?
Why ask it
A skip-level is worth having mainly for context you cannot get from your own manager. This opens with the part of their job that is invisible to you, which is where most of the surprises in your next six months are hiding.
What are you most worried about right now?
Why ask it
Worry is more specific than priorities, and it is usually said plainly. If the answer is a risk your team could reduce, you have found the highest-leverage work available to you.
How does our team's work show up in conversations with your peers?
Why ask it
This tells you how your output is described when nobody from your team is in the room, which is the version that shapes budget and headcount. A vague answer usually means your work is not being talked about at all.
What is our team known for outside the group?
Why ask it
Reputations are often out of date, and they are almost never what a team believes about itself. Hearing that you are known for being slow or for rescuing other people's problems is more useful than any survey.
Which of our numbers do you actually look at?
Why ask it
Teams report far more metrics than anyone reads. The answer tells you which dashboard is worth maintaining, and often reveals that the number they watch is not one you report.
What has changed in your priorities since the start of the year?
Why ask it
Strategy shifts reach individual contributors late and in summary. Asking what moved, and why, gets you the reasoning rather than the announcement, which is what lets you predict the next change.
Where do you think we are slower than we should be?
Why ask it
Managers two levels up see cycle time rather than effort, so this surfaces a mismatch you can fix. Their answer may be unfair, and knowing about the perception is still valuable.
If you had to cut something we do, what would go first?
Why ask it
This is a ranking question disguised as a hypothetical, and it exposes what they consider low value. If the thing they would cut is the thing you spend most of your week on, that is worth knowing now rather than at review time.
Where do you think our plan for the next year is weakest?
Why ask it
Distance makes gaps easier to see, and skip-level managers usually hold a doubt they have not raised because it felt like second-guessing. Ask directly and they will often say it.
What feedback about the team are you hearing that we might not be?
Why ask it
Complaints from other teams tend to travel upward and sideways rather than to the team itself. This is the most reliable way to hear the thing people say about you in other meetings.
What does strong performance at my level look like from where you sit?
Why ask it
The view from two levels up is often about scope and reliability rather than the individual tasks your manager tracks. Where the two definitions differ, you have found why good reviews sometimes fail to lead anywhere.
What would you want to see from someone hoping to move up a level?
Why ask it
Ask for evidence rather than qualities: what they saw the last person do before promotion. Any answer that stays at the level of adjectives means the bar is not written down, which is itself worth knowing.
How do you decide where new headcount goes?
Why ask it
This explains why your team is short-staffed better than any conversation with your own manager will. It also tells you what kind of case wins, which is usually evidence of a bottleneck rather than an appeal to workload.
What is something you have changed your mind about recently?
Why ask it
The answer shows whether new information actually moves them, and what kind of information does it. A leader who cannot think of anything is telling you how much point there is in bringing them a counterargument.
What is happening elsewhere in the company that will affect us in six months?
Why ask it
Reorganizations, platform changes, and shifting budgets are usually visible a level up long before they are announced. Even a guarded answer tells you which direction to watch.
How do you want us to handle disagreements with another team?
Why ask it
You are asking when to escalate and when to settle it yourselves, which is a rule most teams learn by getting it wrong once. Ask what escalation looks like when done well here.
What is the best way to bring you a problem?
Why ask it
Some managers want a written summary in advance, others want it raised in the moment. Getting the format right is often the difference between a problem being acted on and being noted.
What would you want to hear from me that you might not hear from my manager?
Why ask it
This invites them to name the gap they think exists in their information, and it does so without asking you to criticize anyone. Answers usually point at friction, morale, or how long work really takes.
Is there anything you would like me to take back to the team?
Why ask it
It gives the meeting a purpose beyond your own development and often produces a message they have been failing to land. It also gives you a legitimate reason to report back to your own manager.
How often should we do this, and what would make it worth your time?
Why ask it
Closing on cadence turns one meeting into a channel. Asking what would make it valuable to them is also the fastest way to learn whether this was a routine exercise or something they actually want.
How to handle a skip-level without creating problems
Practical guidance for the conversation itself
Be clear what the meeting is for
It is not a status update
Your skip-level manager can get progress from your manager. Spending the slot on what you shipped last month wastes the one conversation where you can ask about context and direction.
It is not a complaint channel about your manager
Raising ordinary friction here usually rebounds, because the two of them talk. If the issue is serious, say so plainly and directly rather than working it in sideways as an aside.
It is a chance to trade information
You have detail they lack about how work actually goes, and they have context you lack about where the organization is heading. Treat it as an exchange and both sides get something.
Preparing
Tell your manager you are going
Skip-levels go badly when a manager is surprised by one. A one-line mention beforehand removes the suspicion that you went around them, which is the only real risk in the meeting.
Pick three questions, not twenty
Half an hour supports three real questions with follow-ups. Choose one about direction, one about how your work is seen, and one about what they need, then let the conversation run.
Have one specific thing to offer
A concrete observation from the ground, a recurring blocker with a number attached, a piece of customer feedback. It makes you memorable for the right reason and gives them a reason to meet again.
Common pitfalls
Asking questions you could have looked up
Anything answered by the strategy deck or the last all-hands burns credibility. Read the material first, then ask about the part that did not make sense.
Performing rather than asking
Questions built to display your own strategic thinking are transparent and they get short answers. Ask the thing you genuinely want to know and the conversation will be better.
Speaking for the whole team without checking
If you raise team-wide morale or workload, be sure it is not just your own view. Getting contradicted later by a colleague is worse than having said nothing.
Letting the answers evaporate
Most of the value is in what you do with the context afterward. Notes plus one changed decision are what separate a useful skip-level from a pleasant chat.
Afterward
- Write down what you learned about priorities and how your team is perceived, in their words.
- Tell your manager what you discussed, especially anything relevant to the team's plans.
- Pass on whatever they asked you to relay, and do it promptly so the request keeps its value.
- Send a short thank-you with one line on what you are doing differently as a result.