Questions to Ask at a Skip Level Meeting
Questions for an employee meeting their manager's manager. 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. Includes what to avoid saying.
The questions
Open any question for the note
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.
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.
In the room
- 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.