By Andreas Pettersson, Founder, Leaders ADAPT
An invite from your boss's boss lands on your calendar. Thirty minutes, next Tuesday, no agenda. The first thing most people do is check whether anyone else on the team got one. The second is to search for how to prepare for a skip-level meeting as an employee and find a list that says "bring your wins."
I have sat in the other chair, as the CEO of a company that grew past 150 people, and I can tell you what the person across the table is actually listening for. It is not a summary of your projects. Here is the preparation that leaves you with something, and the leader too.
Quick answer: To prepare for a skip-level meeting as an employee: find out why it is happening (usually a standing practice, not a warning); write down two things that are working and one that is frustrating, with specifics; prepare two or three questions about direction and expectations; decide in advance what you will not say about your manager; and plan a short follow-up note. Bring judgment, not a status report.
First, should you be worried?
Almost never. Most skip-level meetings are a standing practice: the leader talks to a rotating sample of people two levels down to hear how the work feels before it reaches them edited. If several people on your team got the invite, or it is a quarterly habit, it is routine.
A skip-level meeting is a one-on-one between an employee and their manager's manager, held without the direct manager, so the leader can hear the employee's experience directly. Notice what is not in that definition: evaluation. A skip-level is not a review, and a leader who runs it as one is doing it wrong. The leader's side of the practice, purpose and cadence included, is in the complete guide to skip-level meetings.
The one honest check: ask your own manager. "I've got a skip-level with [name] next week, is that the usual round?" A good manager will tell you exactly what it is. If your manager did not know about it, prepare a little more carefully, not because you are in trouble but because the leader may be new to the practice.
What your skip-level manager is actually listening for
Here is the view from the other chair. When I was the CEO, information reached me late and edited. Not because people lied, but because every layer softened the story a little, and because people had learned that speaking up to the person in charge costs something and staying quiet costs nothing. I call the result the Information Gap, and the skip-level is one of the few tools against it.
The leader across from you is listening for four things.
Specifics. "Things are going well" is a polite noise. "The new release checklist cut our Friday incidents" is information.
Judgment. Not what happened, but what you make of it. A leader remembers "I think we are optimizing the wrong metric" long after they forget a list of deliverables.
Ownership. What you own, what decisions you make without asking, when you last made a call on your own. If the answer is "I check everything with my manager," the leader has learned something about how the team is run, and it is not about you.
Whether you will tell them something true. The rarest thing in that chair is an honest answer to "what would you change?" Give them one, with care.
How to prepare for a skip-level meeting as an employee: five steps
1. Find out what it is
Ask your manager, as above. Read anything the leader has written internally about skip-levels, and if the invite named topics, prepare for exactly those.
The skip-level meeting template most leaders borrow from covers four questions: what is working, what is frustrating, what you would change, and whether anything is hard to raise with your manager. Assume some version of those.
2. Write down two wins and one friction, with detail
Two things that are working and why. One thing that is frustrating, described as a problem and not a person, with what you have already tried. That last clause matters most: "the handoff between design and engineering loses a week, and we tried a shared checklist in March" says owner. "Design is slow" says complainer.
If you struggle to see your own contribution clearly, use the 80/20 rule from my coaching work: about 80 percent of what you think your strengths are, everyone around you agrees with. The last 20 percent is the gap, so pick wins that other people would name too.
3. Compress it
Practice saying your win and your friction in under a minute each. I train the teams I work with to structure any update as situation, complication, question, answer. If you cannot get your point into that shape, you are not ready to give it. Train the compressed version before you walk into the room, not while you are standing in it.
4. Prepare two or three questions to ask
Not ten. The questions to ask are the ones that read as an owner rather than a job seeker:
- What is the one thing you wish our team understood about this year's priorities?
- What does great look like in my role, from where you sit?
- What is the biggest risk you see for our part of the business in the next six months?
- Is there something I could take on that would help, that nobody has asked for yet?
More on this in skip-level meeting questions, which covers both sides of the table.
5. Decide what you will not say
This is the step every guide on how to prepare for a skip-level meeting as an employee skips. Decide before the meeting what, if anything, you will say about your manager, and how. The next section is about that.
How to raise a concern about your manager without going over their head
The rule I have published before, in my field guide to managing up, and will repeat: never go over your manager's head first. A skip-level complaint reads as gossip, and it quietly destroys trust with both people. The person with the feedback gets it first, always. If you have never done that, how to give your boss feedback is the place to start, before the skip-level, not after.
So the test for anything about your manager is simple. Have you raised it with them directly, ideally in your own one-on-one meeting with your manager? If yes and nothing changed, you can name it in the skip-level as a problem you have already tried to solve. If no, the honest answer to "is there anything you can't tell your manager?" is "there's something I should raise with her first, and I will."
When you do raise something, separate the problem from the person. "Our one-on-ones have become status updates and I'd like more coaching" is a problem the leader can act on and your manager can hear as a theme. "My manager doesn't develop people" is a verdict, and leaders do not act on verdicts from one conversation.
The exception is real harm: ethics, safety, harassment. Those go up immediately.
What not to say in a skip-level meeting
Four things that cost more than they earn.
A status report. The leader can read that, and every minute you spend on it is a minute of judgment they did not get from you.
"How am I doing?" It asks the leader to evaluate you in your manager's absence, which puts them in an awkward spot and your manager in a worse one. Ask what great looks like instead; you will get the same information without the politics.
A promotion ask. A skip-level is where you become known for judgment; the promotion conversation belongs with your manager, and a leader who has seen your judgment will be a better ally when it comes.
Anything you would not want your manager to hear as a theme. Assume everything may travel back without your name, and say only what you would stand behind if it did.
How to use a skip-level to get sponsorship without asking for a promotion
In Power Without Permission I drew a line that applies here. Mentorship nurtures growth; sponsorship accelerates advancement, because a sponsor advocates for you when you are not in the room. Your manager can mentor you. Your manager's manager is the first person in your career who can sponsor you, and a skip-level is the moment they decide whether to. That is the real visibility a skip-level offers, and it is why managing up, done well, includes the level above your manager.
Sponsors are not won by asking. They are won by showing that you see the business and not just your task, that you can deliver an unwelcome truth carefully, and that you follow through. Which brings us to the last step.
After the meeting: the follow-up that most people skip
Within two days, send a three-line note: thank you, the one thing you took from the conversation, and the one thing you committed to, with a date. If the leader committed to something, do not chase it; mention it once when you next meet.
Then, if the leader passes your friction back to your manager as a theme, help your manager fix it. That is the loop closing in the only direction that helps your career.
Frequently asked questions about preparing for a skip-level meeting as an employee
How do you prepare for a skip-level meeting as an employee?
The short version of how to prepare for a skip-level meeting as an employee: confirm with your manager that the meeting is a standing practice, then prepare three things: two specific wins and one friction described as a problem with what you have already tried, two or three prompts about direction and expectations, and a decision about what you will and will not say regarding your manager. Practice stating each point in under a minute. Plan a short thank-you note for afterwards that repeats any commitment you made.
Should I be worried if my skip-level manager schedules a meeting?
Usually not. Most skip-level meetings are part of a rotating practice in which a leader talks to people two levels down to hear how work feels without the filtering of a middle layer. Signs it is routine: several colleagues received the same invite, it recurs quarterly or yearly, and your manager knows about it. A skip-level is not a performance review, and a leader running it that way is misusing the format.
What can an employee ask in a skip-level meeting?
Strong asks are about direction and expectations: what the leader wishes the team understood about this year's priorities, what great looks like in your role from their seat, what risk they see for your part of the business in the next six months, and whether there is something you could take on that nobody has asked for. Two or three are enough. Avoid asking how you are doing or about promotion timing.
What should you say in a skip-level meeting?
Say specific things: what is working and why, one frustration framed as a problem with what you have tried, and a considered answer to what you would change about how the team or company works. Offer judgment rather than a list of tasks, and be prepared to say what you own and what decisions you make on your own. Close with your prepared asks and confirm anything you committed to.
What should you not say in a skip-level meeting?
Avoid a status report the leader could have read, anything that asks the leader to evaluate you in your manager's absence, promotion requests, and complaints about your manager that you have not first raised with them directly. Anything said in a skip-level may travel back to your manager as a theme, so say only what you would stand behind if it did. Real harm such as ethics or safety issues is the exception and should be raised.
How is a skip-level meeting different from a skip-level interview?
A skip-level meeting is a conversation between a current employee and their manager's manager about how the work and team feel. A skip-level interview is a hiring step in which a job candidate meets the hiring manager's boss, usually to assess fit with the wider organization. Preparation differs: the interview calls for examples of past work and curiosity about the team's direction, while the meeting calls for honest observations about current work.
Thirty minutes, one sponsor
A skip-level meeting is not a test you pass by having good answers. It is thirty minutes in which someone two levels up decides whether you see the business, whether you can tell the truth carefully, and whether you follow through.
That is how to prepare for a skip-level meeting as an employee: two wins, one friction, three asks and one decision about your manager, then spend the meeting being useful to the person across the table. Sponsors advocate for you when you are not in the room. This is how they start.
Know your own leadership type before you walk in
The leader across from you is reading your type as much as your answers: systems or people, driving or steadying a room. It helps to know it yourself first. The free leadership assessment takes about ten minutes and gives you your type and default style, which is a better thing to bring into a skip-level than a rehearsed list of accomplishments. Take it before Tuesday.
Andreas Pettersson wrote Power Without Permission after ten years as a tech CEO, including his time as one of Canon's youngest CEOs. He founded Leaders ADAPT.
