Questions to Ask at a Skip Level Meeting
Good questions to ask your boss's boss, written for an employee who has a meeting with their manager's manager on the calendar. They are built around what a skip-level can tell you that your own manager cannot: how decisions upstream were actually made, what is coming, and how the work of your team looks from a level up. The guide below sorts what to ask during a skip level meeting from what to avoid saying.
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The questions
Each question, and why to ask it
What are you hoping to get out of these meetings?
Why ask it
Skip-levels exist for different reasons, and knowing which one you are in changes how you use it. Some leaders run them to catch problems their managers are filtering, some to be visible, some because a survey score told them to. If the answer is thin, treat it as a listening session rather than a place to raise anything sensitive.
What are you spending most of your own time on at the moment?
Why ask it
This reveals what the level above you is actually made of, which is usually less strategy and more negotiation over budget, headcount and other departments than people assume. It also tells you which problems are live upstream. What they are spending time on is a better guide to real priorities than any published list of goals.
What's the thing you're most worried about for this group right now?
Why ask it
You get their actual risk register rather than the roadmap. Answers tend to be concrete: a delivery date, a customer, a key person who might leave, a reorganisation. Knowing it lets you connect your work to something that matters, and it is the single most useful thing to walk out with.
How much do you want me to bring things to you directly, versus route them through my manager?
Why ask it
Ask this early, because getting it wrong damages the relationship you depend on most. Some leaders genuinely want an open door and some will forward your message to your manager within the hour. Their answer sets the rules for everything else you say in the room.
Which recent decisions do you think people at my level don't understand the reasoning behind?
Why ask it
This is the highest-value question in a skip-level, because context is what gets lost travelling down an organisation. You often learn that a decision everyone reads as arbitrary had a constraint behind it nobody explained. It is also easy for them to answer, since the gap between what they decided and what people heard usually annoys them too.
Is anything changing in the next few months that I should be getting ready for?
Why ask it
Phrased this way it is answerable without breaking a confidence, and you may hear about a reorganisation, a tooling migration or a shift in priorities weeks before it is announced. Notice what they decline to answer as well as what they say. A careful non-answer usually means something is coming.
How is our team's work seen by the people you report to?
Why ask it
Reputation two levels up is invisible from inside a team and it determines headcount, interesting projects and how much benefit of the doubt you get. You may learn that work you consider routine is what the team is known for, or that a project you are proud of nobody upstream has heard of. Both are directly actionable.
Where do you think we're slower than we should be?
Why ask it
This invites a criticism of process rather than of people, so it is safe to ask and usually gets a real answer. Leaders see the delay between a decision and a result in a way that people inside the work do not. Ask what they think causes it, since their theory may be wrong in a way you can correct with what you know.
What are we doing that you'd stop?
Why ask it
Almost every team carries work that continues because it always has, and a level up is often where the pointlessness is most visible. If they name something you own, you have learned something valuable before it appears in a review. If they cannot name anything, ask what they would do with twenty percent more of the team's time.
Where does the information you get about our team get lost or filtered?
Why ask it
It is a candid question that most leaders enjoy, because they know it happens and cannot see where. The answer tells you which of your updates are actually read, and by whom. It also opens the door to offering the kind of detail they are missing without going around your manager.
What do people at my level most often get wrong about how decisions get made here?
Why ask it
You are asking for the real decision-making map rather than the organisational chart: who has to be persuaded, which forum matters, how long things take. This knowledge is most of what separates effective senior people from capable junior ones. It is also rarely written down anywhere.
Is there work happening elsewhere in the company that overlaps with ours?
Why ask it
Duplication is nearly invisible from inside a team and obvious from above. Finding out saves wasted months and sometimes produces a useful ally two departments away. If the answer is yes, ask who you should talk to, which converts the information into an introduction.
What skills is this group going to need in two years that we're short on now?
Why ask it
This turns career development into something concrete and forward-looking rather than a request for advice. The gap they name is where investment and promotions will go, and being early to it is worth more than performing well at something already covered. Ask whether they would support you learning it on work time.
How do you decide where headcount and budget go?
Why ask it
Once you know how allocation works, a refusal stops looking arbitrary and becomes something you can make a better case against next time. You may learn that the constraint is a hiring freeze rather than a judgement about your team's value. Leaders are usually willing to explain this and are rarely asked.
What separates people at my level who move up from people who stay where they are?
Why ask it
Asked of a skip-level rather than your manager, this gets you the criteria as they are applied at the level where promotions are approved, which is often not what the published ladder says. Listen for whether the answer is about scope, visibility, or a specific type of work. Vague answers about attitude mean the process is informal, which is itself worth knowing.
Do you see my work at all, and if so, how does it reach you?
Why ask it
The honest answer is often that they see very little of it and only through your manager's summaries. That is not a slight, it is a structural fact about how organisations pass information, and knowing it tells you whether to change what you document. Being useful two levels up usually depends on written artefacts rather than performance in meetings.
Has any feedback about me reached you?
Why ask it
Ask this calmly and only if you can take an unflattering answer well. Most of the time the answer is no, which is neutral information. Occasionally you learn about an impression forming at a level you cannot otherwise see, and hearing it now is much better than hearing it in a calibration cycle.
What would you want to know about how the work actually happens down here?
Why ask it
This is the trade that makes a skip-level worth their time. You hold detail they cannot get: where the process breaks, what the tooling costs in hours, what customers say. Answer honestly about systems and workload rather than about individuals, and you become someone they want to meet again.
What's something you got wrong recently, and what did you change?
Why ask it
Save it for a second or third meeting, once there is some rapport. A specific answer tells you it is safe to be wrong in this organisation, which is one of the most consequential facts about a workplace. A leader who has made no mistakes is describing a culture where errors get hidden.
If you were in my role, what would you focus on this quarter?
Why ask it
Concrete and time-bounded, so it produces a recommendation rather than encouragement. It also lets you check their picture of your role against the reality, and a wildly inaccurate answer tells you your work is not visible upstream. Whatever they name, you can reference it later as agreed direction.
Who else should I know, and would you introduce me?
Why ask it
Introductions are the one thing a skip-level can give you cheaply that is genuinely hard to get on your own. Ask for a name and an offer to send an email, not just advice to reach out. Follow up within a couple of days while the offer is still warm.
How often should we do this, and what would make it useful for you?
Why ask it
Close by making the meeting recurring on their terms rather than hoping for another invitation. Their answer also tells you honestly what the relationship is: a standing quarterly slot is different from an open door you should not use. Send a short follow-up with anything you promised.
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.
What are the two or three numbers you get judged on?
Why ask it
Their metrics explain their behavior better than any org chart, including which requests they will always say yes to. If your work does not visibly move any of those numbers, you have found out why it keeps sliding down the list.
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.
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.
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 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 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 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.
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.
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 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.
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 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.
Looking a year out, what would make you say this team succeeded?
Why ask it
A specific answer gives you a target that survives quarterly reshuffles. If they cannot name one, the team's direction is being set at your manager's level and you should calibrate your expectations accordingly.
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.
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.
Is there anything about where the company is headed that you cannot discuss yet?
Why ask it
Asking permission to not know saves you from repeatedly probing a closed door, and most leaders will confirm the boundary honestly. A clear no comment about one area is more informative than a vague answer about all of them.
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.
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.
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.
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.
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.
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.
What is the mistake you see repeated at my level?
Why ask it
Asking about the pattern rather than about yourself makes it easy to answer honestly, and the pattern almost always applies to you at least partly. Common answers involve escalating too late or optimising for visible work over useful work.
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.
What is something my manager is handling well that I probably do not see?
Why ask it
This keeps the conversation from drifting into complaint while producing real information. What gets absorbed by a manager, such as shielding the team from churn above, is invisible by design.
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.
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.
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 to use a skip-level well
Practical guidance for the conversation itself
What a skip-level is, and is not
It is not a performance review
Your skip-level almost certainly does not know your work in detail. Asking them to assess your performance puts them in an awkward position and produces a generic answer. Use the meeting for context, direction and introductions, and keep the evaluation conversation with your manager where it belongs.
It is not a back channel for complaints about your manager
Even a mild criticism will usually reach your manager, sometimes in a distorted form, and it costs you more than it gains. If you have a serious problem, such as harassment, retaliation or something unlawful, that is a matter for HR or an ethics line, not a skip-level chat. If the issue is a difficult but ordinary working relationship, raise it with your manager first and say so honestly if asked.
Tell your manager you are going
In most companies skip-levels are scheduled openly, but if this one came directly to you, mention it to your manager beforehand in one line. Managers who find out afterwards tend to assume the worst, and the cost of the awkward assumption is far higher than the cost of the sentence.
Assume a small audience, not a private room
Treat anything you say as something that might be repeated, in summary, to your manager or to their peers. That does not mean being guarded, only that you should raise systems and workload rather than personalities, and say things you would be comfortable owning.
Preparing for thirty minutes
- 1Choose three questions, not twenty. Half an hour with a senior person supports roughly three real exchanges and one piece of follow-up.
- 2Look at what they have said publicly, in all-hands notes, internal posts or strategy documents, and ask about a specific point from it. This is the single easiest way to be a memorable conversation.
- 3Prepare one useful thing to offer: a pattern you see in customer feedback, a step in a process that costs hours, a risk nobody has flagged. Give as well as take.
- 4Have a two-sentence answer ready for 'what are you working on', without jargon your skip-level may not share.
- 5Decide beforehand what you will not raise, so you do not improvise a complaint under the pressure of a friendly conversation.
During the skip level meeting
- Let them talk more than you do. You are there for information that does not travel downward on its own.
- Ask about mechanisms rather than opinions: how a decision was made, who was involved, what the constraint was.
- If they ask what is not working, answer about process and load rather than about individuals, and bring a suggestion with the problem.
- Do not ask for a promotion or a raise. Skip-levels rarely own that decision and it makes the rest of the conversation transactional.
- Write down names, numbers and any commitment they make while it is fresh.
Afterwards
- Send a short note the same day, thanking them and confirming anything you offered to do or send.
- Tell your manager the substance of what you discussed, at least in outline. It removes any suspicion and often turns useful context into a shared plan.
- Act on one thing you learned within a fortnight, and mention it next time. Following through is what turns a single meeting into an ongoing relationship.
- If you were promised an introduction, chase it once, politely, after a week.
- If the meeting made clear that your work is invisible two levels up, fix the artefacts rather than the visibility: a clearer written update, a summary your manager can forward as it stands.