Questions to Ask During a Skip Level Meeting
Questions for a half hour with your manager's manager, written for the awkward version where you have never had one before and are not sure what it is for. Covers what they are trying to learn, what they are deciding, and how to be useful without going around your own manager.
The questions
Open any question for the note
What are you hoping to get out of these meetings?
Why ask it
Skip levels serve different purposes: some leaders are checking morale, some are testing whether messages are landing, some are looking for people to promote. Asking first lets you spend the remaining time on what they actually want, which is also the time best spent for you.
What are you being asked to deliver this year that I probably do not see?
Why ask it
Two levels up, the pressures are usually budget, headcount, a cross team commitment or a board level number. Hearing them explains decisions that look arbitrary from below, and it gives you a way to frame your own work in terms they already care about.
Which of our team's projects matters most to you, and why that one?
Why ask it
The ranking is often not the one your team assumes, and the reason is more useful than the ranking. If your main piece of work is not on the list, that is worth knowing now rather than at review time.
What do you hear about our team from other parts of the organisation?
Why ask it
This is information you cannot get anywhere else, and it is usually specific: slow to respond, hard to get answers from, reliable but late. Reputation shapes what work comes your way, so knowing the current version is genuinely valuable.
Is there something we do that you wish we would stop?
Why ask it
Most senior people have an answer and rarely get asked for it. A meeting, a report, a habit of escalating, a process that has outlived its purpose. It is also one of the few questions where you can act on the answer within a week.
Where do you think we are slower than we should be?
Why ask it
The answer shows you what looks like friction from above, which is often a handover or an approval step nobody owns. If they name something you know the cause of, this is the moment to explain it, briefly, without blaming anyone.
What decisions are you making now that will change my work in the next six months?
Why ask it
Reorganisations, tool changes, headcount and priority shifts are usually visible upstairs months before they are announced. You may not get details, but you will learn whether to plan for stability, and that changes what you commit to.
What are you uncertain about, where hearing from the ground would help?
Why ask it
This turns the meeting into something they get value from, which is what makes them want the next one. It also tends to produce the most honest part of the conversation, because you have asked them to admit a gap rather than explain a plan.
How do you prefer to hear bad news?
Why ask it
Some leaders want the problem the moment you see it, some want it with an attempted fix, and some want it only through your manager. Getting this wrong is how people damage a relationship with a skip level, and the question costs nothing to ask.
When something is stuck between teams, when should I bring it to you?
Why ask it
You are asking for a threshold, which protects both you and your manager. A good answer names the size or duration that justifies escalation. An answer inviting you to bring anything at any time is worth clarifying, since taking it literally rarely ends well.
What is your honest read on the last thing we delivered?
Why ask it
Ask about the work, not about yourself, and you tend to get a franker answer. Praise phrased in generalities usually means they did not follow it closely, which is itself useful, and specific criticism is the most valuable thing you can leave with.
How is our team's work measured at your level?
Why ask it
The metrics reported upward are often not the ones your team tracks, and the gap explains a lot of mismatched expectations. Knowing what appears on their dashboard lets you tie your own updates to numbers they already look at.
What skills do you think we are short of?
Why ask it
The answer tells you where the next hire, and the next opportunity, will be. If you can credibly develop toward that gap, you have found the most direct route to more responsibility that exists in the organisation.
From where you sit, what does the step from my level to the next one look like?
Why ask it
Two levels up is where promotion decisions are usually approved, so their description carries more weight than the written framework. Listen for what they mention that the framework does not, since that is the real bar.
What tells you someone is ready for more responsibility?
Why ask it
Expect something behavioural rather than technical: handling a difficult stakeholder, being trusted with an ambiguous problem, raising a risk early. Whatever they say, it is the standard you are being judged against, and now you have it in their words.
Who should I know in the organisation that I probably do not?
Why ask it
This is the single highest value ask in a skip level, because senior people can make introductions in one message that would take you months. Ask for a name and offer to reach out yourself so it costs them nothing.
What has changed in company priorities that has not fully filtered down?
Why ask it
Strategy loses detail on the way down, and the version your team is working from may be a quarter out of date. Even a short answer here lets you avoid work that has quietly stopped mattering.
What is the hardest part of your job that people at my level misjudge?
Why ask it
It invites a real answer and shows you are curious about the role rather than lobbying. It also gives you a more accurate picture of the level above, which is worth having before deciding whether you want it.
Is there anything you would like me to look into before we next speak?
Why ask it
Leaving with a task, however small, turns a pleasant chat into a working relationship. It also gives you a legitimate reason to make contact again, which is otherwise the hardest part of a skip level relationship to sustain.
How often would you like to do this, and what would be most useful for me to bring?
Why ask it
You are asking them to set the cadence rather than guessing, which avoids both chasing and disappearing. Their answer about what to bring, whether that is problems, data, or nothing at all, tells you how they use these meetings.
Using a Skip Level Well
Practical guidance for the conversation itself
Before and During
Tell your manager you are going
If the meeting was arranged over their head, mention it and ask if there is anything they would like raised. Skip levels damage relationships mainly through surprise, and a thirty second conversation removes almost all of that risk.
Bring three questions and one piece of information
The information matters as much as the questions: a customer pattern you keep seeing, a step that wastes an hour a week, a risk nobody upstairs has heard about. It gives them a reason to remember the meeting.
Talk about the work, not the people
Describe processes, handovers and decisions rather than individuals. The same point lands as insight when framed as a system problem and as a complaint when framed as a person problem.
Be brief and let them talk
Aim to speak for less than half the time. You already know your own view, and the whole value of the meeting is in what they say. Silence after a question usually produces the most useful sentence in the meeting.
Follow up once, in writing
A short note the same day with what you took away and anything you offered to do. It is the difference between a meeting they remember and one that blurs into the other five they had that week.
Two Sequences That Work
If it is your first skip level
- 1What are you hoping to get out of these meetings?
- 2What are you being asked to deliver this year that I probably do not see?
- 3What do you hear about our team from other parts of the organisation?
- 4How do you prefer to hear bad news?
If you are aiming at the next level
- 1From where you sit, what does the step from my level to the next one look like?
- 2What tells you someone is ready for more responsibility?
- 3What skills do you think we are short of?
- 4Who should I know in the organisation that I probably do not?
Common Mistakes
Using it to go around your manager
Raising a complaint about your manager in a skip level almost always travels back, usually within days. If the issue is serious enough to need escalation, take it to HR or raise it directly, not in a relationship building meeting.
Arriving with nothing
Waiting to be asked questions turns thirty minutes into small talk, and senior people quietly stop scheduling these with people who bring nothing. Two prepared questions are enough to avoid this.
Pitching yourself for the whole slot
A skip level is not a performance review. Lobbying for a promotion for thirty minutes reads as self interested, whereas asking what readiness looks like achieves the same thing and leaves a better impression.
Repeating something they already said publicly
Check the last all hands or written update before you go. Asking about strategy they explained last week wastes the rare access you have, and asking about what it means for your team does not.