Questions to Ask Your Skip Level Manager
Twenty questions for a meeting with your manager's manager, covering the priorities and constraints that never travel down the org chart, how promotion and headcount decisions actually get made, and how to keep your own manager informed so the meeting does not backfire.
The questions
Open any question for the note
What's changed in your priorities recently that probably hasn't reached us yet?
Why ask it
Strategy decays between levels, and the version your team is working from can be a quarter out of date. Only someone at their level can answer this, which is what makes it the best use of the slot.
What is your own leadership asking you about right now?
Why ask it
Whatever their boss is pressing them on is what will get funded and defended. If they cannot name anything, they are either being deliberately vague or genuinely outside the decisions.
Where do you think our team is strongest, and where do you wish we were better?
Why ask it
Asking about the team rather than yourself is what keeps a skip-level from reading as a bid for attention. The second half of the question is where the real information sits.
What decisions would you rather we made without asking you?
Why ask it
You learn how much autonomy you actually have, which is usually more than people assume. Managers rarely announce this and often complain privately about approving things they do not care about.
When our work reaches you, what's usually missing?
Why ask it
Gets at the gap between what your team produces and what leadership needs to act. A specific answer, often about cost, risk or timing, saves a quarter of guessing.
What do people at my level tend to misunderstand about how decisions get made here?
Why ask it
Invites them to correct a misconception instead of defending the process. Expect to hear that decisions are slower, more budget-bound, or less deliberate than you had assumed.
If you had to cancel one of our projects, which would it be?
Why ask it
Blunt, and it forces a ranking they already carry privately. If your own project is the answer, you would rather hear it now than during a reorganization.
How do you decide where headcount goes?
Why ask it
Headcount is the clearest statement of priority any organization makes. How they describe the process shows where the real leverage sits, which is often not with them.
What are you worried about that we probably aren't?
Why ask it
Surfaces the risk visible only from higher up: a customer, a dependency, a budget cycle, a pending reorganization. Even a partial answer changes what you watch.
Where does our team's work actually end up? Who uses it?
Why ask it
Two levels up they know who consumes your output and who ignores it. This often reveals that a report you maintain has no readers, or that something you treat as minor is load-bearing elsewhere.
What does someone at the next level up do differently, day to day?
Why ask it
Ask for behavior, not attributes. Answers like ownership and strategic thinking mean nothing, so keep pushing until you get a description of something a person does on a Tuesday.
How do promotions here actually get decided, and who's in the room?
Why ask it
The published criteria and the real process rarely match, and a skip-level knows both. Who is in the room matters more than the criteria, because it tells you whose opinion of you needs to exist at all.
What have you seen me do that you'd want more of?
Why ask it
More useful than a general request for feedback, which mostly produces reassurance. Whether they can name anything also measures how visible you are two levels up, which may be less than you hope.
Am I doing anything that creates extra work for my manager or for you?
Why ask it
Almost nobody asks this, and it stands out immediately. The usual answers are escalating too early, escalating too late, or sending updates in a format that has to be rewritten before it can be passed on.
What skill is scarce on this team right now?
Why ask it
A concrete capability gap is far more actionable than advice about developing yourself. If they name something you already do, say so, because it means it is not visible from up there.
Who outside our team should I know, specifically?
Why ask it
Ask for names rather than departments. A skip-level can make an introduction in one message that would otherwise take you six months to arrange.
What did you get wrong earlier in your career that you'd tell me to avoid?
Why ask it
Lets them be candid without evaluating you, which is why it often draws the most honest answer of the meeting. It usually surfaces something about how they handled a boss or a failed project.
When something concerns me, do you want to hear it directly or should it go through my manager first?
Why ask it
Defuses the main hazard of skip-levels, which is your own manager learning you went around them. Agree the route now and you can use it later without it looking like an escalation.
Is there anything you'd like to know about how things look from where I sit?
Why ask it
The exchange these meetings exist for. Bring one concrete observation about a process, a tool or a customer, rather than a complaint about a person.
What would make this worth repeating in six months?
Why ask it
Establishes whether this becomes a standing relationship or a one-off. A vague answer means they treat skip-levels as a formality, which tells you how much to invest in the next one.
Making a skip-level meeting worth the slot
Practical guidance for the conversation itself
Before the meeting
- Find out what their organization is measured on: revenue, retention, uptime, cost, headcount. Question quality depends almost entirely on knowing this.
- Bring three questions, not fifteen. Thirty minutes with real follow-ups covers about three.
- Have one thing to offer: a pattern in customer complaints, two teams duplicating work, a process that costs your team a day a week.
- Decide what you want to walk out with, whether that is a name, a decision, or a clearer read on the next twelve months.
Keeping your own manager onside
- Tell your manager you have the meeting and roughly what you plan to ask, even when the invitation came from above.
- Afterwards, pass anything relevant to your manager before the skip-level does. Being the source is what keeps the trust intact.
- If your real problem is with your manager, a meeting about department strategy is the wrong venue. Ask for a separate conversation, or go to HR.
- Never start a sentence with what your manager said, unless you would say it in front of them.
What not to bring
- Complaints about named colleagues. Two levels up, the name sticks to you at least as much as to them.
- Questions answered on the intranet. They burn the only scarce resource in the room, which is attention.
- A pitch for your own promotion in a first meeting. Ask what the bar is rather than arguing that you have cleared it.
- Anything you have never raised with your own manager. Skip-levels are for context, not appeals.
Afterwards
- Send three lines the same day: what you took away, what you will do differently, the one thing you will follow up on. Short enough to read on a phone.
- Do the follow-up. That is what separates the people who get invited back.
- Ask for a repeat at a stated interval rather than leaving it open. Quarterly is normal and easy to agree to.
- Write down what they said the priorities were. In six months you will be able to see whether the stated priorities and the funded ones matched.