Questions to Ask During Skip Level Meetings
Questions for a half-hour meeting with your manager's manager, aimed at context you cannot get from your own manager. Written for the employee side of the conversation, including what to avoid raising.
The questions
Open any question for the note
What are you hearing about our team from outside it?
Why ask it
Senior managers sit in rooms where your team is discussed without anyone from it present. This is the single most useful thing they can hand you, and it is often quite different from your internal view of how things are going.
Which of our projects would hurt most if it stopped tomorrow?
Why ask it
It forces a ranking rather than a list of priorities. If the answer is not the project consuming most of your team's time, that gap is the most actionable thing you will learn all quarter.
What changed in your priorities recently that has not filtered down yet?
Why ask it
Decisions take weeks to reach individual contributors, usually arriving as an unexplained reshuffle. Asking directly gets you the reasoning while it still helps you plan.
What decisions are you making that our work depends on?
Why ask it
Teams frequently build on assumptions that are still under debate two levels up. Knowing which of those are genuinely open lets you avoid work that will be discarded.
Where do you think we are spending effort that no longer matters?
Why ask it
Nobody at your level is allowed to retire a project, but a skip level can tell you which ones they have stopped caring about. Expect a specific report, meeting or integration to be named.
What do you wish people at my level would bring to you directly?
Why ask it
Sets the terms for the rest of the relationship, and stops you from either over-escalating or going silent. Answers usually name a category, customer problems, risks, cross-team friction, rather than a frequency.
What does this team look like in a year, in scope and headcount?
Why ask it
You are asking whether the plan is growth, hold or quiet contraction. A confident answer about scope with hedging on headcount usually means more work is coming without more people.
Which other team should I understand better than I do?
Why ask it
Skip levels see dependencies you do not. The team they name is often the one about to affect your roadmap, and knowing someone there before that happens is worth more than the meeting itself.
What is the trade-off you are currently stuck on?
Why ask it
This invites them to think out loud, which is where you learn how decisions here are actually made. It also reveals the constraint they are working against, which is rarely what the strategy deck says.
Which of our metrics do you not trust?
Why ask it
Every leader has one number they quietly discount. Learning which one saves you from optimising a measure nobody senior believes, which is a common way for good work to go unnoticed.
What is the binding constraint on the organisation right now: money, headcount or time?
Why ask it
The answer changes what proposals can succeed. A pitch that saves money lands in one climate and is ignored in another, and only someone at this level can tell you which climate you are in.
What is your own leadership asking you for that we could help with?
Why ask it
It reframes the meeting around their problems instead of yours, and the reply is usually specific enough to act on. It also tells you what your team's work will be judged against.
When my name comes up, what work do you associate with me?
Why ask it
Uncomfortable, and the most valuable question on this list. A blank or a wrong project is not a verdict on your work, it is evidence that the visibility problem is real and fixable.
What would have to be true for someone at my level to be promoted here?
Why ask it
Phrased about the level rather than yourself, it gets a description of the bar instead of feedback on you. Ask who was promoted most recently, because an unused ladder is theoretical.
How do you want bad news to reach you?
Why ask it
Establishing this before something goes wrong is the whole point of asking. Some leaders want the early signal even when it is uncertain; others want it filtered through your manager, and guessing wrong is costly.
What is the last thing you changed your mind about?
Why ask it
Shows whether new information travels upward here. A leader who cannot recall changing their mind on anything is a leader whose team learns to stop raising objections.
Where do you expect us to be least prepared in two years?
Why ask it
Asks for a worry rather than a forecast, which is easier to answer honestly. The gap they name is often a skill the team could start building now at very low cost.
Is there something you have heard about our team that you would like to check?
Why ask it
Gives them permission to test a rumour or a concern with someone close to the work. Answering it plainly, without defending the team reflexively, is what makes them come back to you.
What should I be reading, watching or paying attention to that I probably am not?
Why ask it
A low-stakes question that returns something usable, whether that is a competitor, a regulatory change or an internal document. It also shows you intend to act on the conversation.
What do you wish people asked you in these meetings?
Why ask it
Most skip levels are spent on status updates the leader did not want. This hands them the agenda for next time and often produces the most candid few minutes of the half hour.
Handling a skip level well
Practical guidance for the conversation itself
Before the meeting
Tell your manager you are going
In most companies they already know, but saying so removes the suspicion that you went around them. One sentence about what you plan to ask is enough, and it protects the relationship you rely on daily.
Pick three questions and drop the rest
Half an hour with introductions leaves room for three real exchanges. Trying to cover ten topics produces ten shallow answers and no follow-up.
Do not prepare a status update
They can get status from your manager. Arriving with a progress report wastes the one meeting where you could have asked about the things nobody else can tell you.
What not to raise
Complaints about your manager
Unless there is misconduct, in which case this is the wrong forum and HR is the right one, raising it here reads as an end run. It usually returns to your manager within a day, in a version you did not control.
Requests they cannot grant
Pay and promotion decisions normally sit with your manager and a calibration process. Asking about the standard is useful; asking for an outcome puts them in an awkward position and rarely works.
Gossip and other people's performance
Commenting on colleagues is the fastest way to end up remembered for the wrong thing. Talk about work, dependencies and decisions instead.
Anything you would not say with your manager in the room
A reasonable test for the whole conversation. If the sentence would be a problem overheard, leave it out.
After the meeting
- Write down what they said about priorities and constraints while the wording is fresh
- Tell your manager what you learned, especially anything that affects the team's plan
- Act on one thing before the next meeting, then mention it briefly when you do
- If they named another team, contact someone there within the week
- Keep a running list of questions between meetings so you are not improvising next time