Your manager's manager puts 30 minutes on the calendar and you immediately wonder what it means. You don't know whether to give a project update, ask for career advice, raise a problem, or wait for them to lead.
This article covers what a skip-level meeting is for, how to prepare with your manager, and what questions to ask. It also covers how to discuss career goals, and how to raise a concern without turning the conversation into a complaint. Use the one-page prep sheet before the meeting and the follow-up template afterward.
The advice comes from Nikhyl Singhal, who led product at Meta and Credit Karma; Julie Zhuo, former VP of Design at Facebook; and Jules Walter, a product leader who worked at Slack, YouTube, and Google.
What a skip-level meeting is for
A skip-level meeting gives a senior leader information they can't get from dashboards or management updates. They can hear where priorities are unclear, which processes make work harder, what customers are saying, and what people on the team want to learn.
It gives you a wider view of the company. You can learn which outcomes matter above your team, how leaders make tradeoffs, and which capabilities will matter as the organization changes.
Your own manager is still your main relationship. Bring routine performance questions, promotion asks, and team coordination to them first. Use the skip-level to learn more and to make real issues visible.
Ask your manager for context before you go
Tell your manager you're preparing. That way the meeting doesn't look like you're trying to go around them.
Message to your manager
"I have a skip-level with Maya on Thursday. Do you know what she wants to focus on? I plan to share a short update on the migration, ask about the division's priorities, and discuss the skills I should build for larger projects. Is there context you think would be useful?"
Don't ask for permission to have a normal company meeting. Just let them know and ask what they'd add. If you plan to raise a problem you've already discussed with them, say that too.
Prepare three useful topics
The business
- One question about company or division priorities.
- One tradeoff you want to understand from the senior leader's perspective.
Your work
- A 30-second description of the outcome you own.
- One customer signal, process issue, or opportunity that may matter beyond your team.
Your career
- One skill or type of scope you want to develop.
- One request for advice, exposure, or a person to learn from.
Bring more than you expect to cover. Let their questions decide where the time goes.
Learn what the next level actually requires
Nikhyl Singhal recommends thinking beyond the next title and looking at the work one level after it. A skip-level meeting is a rare chance to ask someone who already sees that wider scope.
Look one role farther ahead. The player below is queued to 8:28, the exact moment Nikhyl Singhal explains the idea behind The Skip. Watch on YouTube.
"I always think about what's not the next job, but the one after it. Maybe think about not your boss's job, but your boss's boss's job, and what do I need to think about to get there?"
Ask questions that get at what the job actually involves:
- "What problems take most of your attention that people at my level rarely see?"
- "What separates someone who is strong in my role from someone ready for broader scope?"
- "Which capability will this organization need more of over the next year?"
- "If you were in my role now, where would you spend more time?"
Give a short update that fits the senior leader
Start with the outcome, the current state, and why it matters beyond your team. Skip the task history unless they ask.
Your 30-second introduction
"I lead the onboarding work for enterprise accounts. Our goal is to cut the time from signature to first value from 30 days to 18. We're at 22 now. The next constraint is implementation capacity, and I'm working with Services on a different handoff."
Jules Walter says you have to adjust the same message for each audience. A CEO and a CFO can hear the same proposal and need different parts of the reasoning.
Adapt the same work to the listener. The player below is queued to 23:17, the exact moment Jules Walter explains how senior audiences differ. Watch on YouTube.
"How do you communicate in an empathetic way? So specifically, you're telling the same story or presentation, but to different audiences, and each time you have to adjust it because the CEO will care about this part, the CFO will care about this other part, and so on."
Before the meeting, write one sentence on why your work matters to their priorities. That's usually enough. If you don't know what they care about, ask instead of guessing.
Get ready for a conversation two levels up
Work Coach marks the point where your 30-second update turned into project history. Say the short version to a stand-in skip-level, so it's been out of your mouth at least once.
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Talk about your career without asking for a promotion
Tell the senior leader what you want to learn and the kind of problem you want to be able to own. Then ask what they think is missing. You get a useful career conversation even when they don't know your day-to-day work well enough to judge a promotion.
Julie Zhuo says to tell your manager what you want and ask which skills you need to build. She's talking about the conversation with your own manager, which should happen before or alongside the skip-level.
Make the aspiration clear. The player below is queued to 1:06:02, the exact moment Julie Zhuo explains the first career conversation to have. Watch on YouTube.
"The first is make sure your manager is aware of those aspirations. Bring them into your hopes and dreams... and the first thing you should ask is, what does it take? Where are the skills that I'm going to need to get better at?"
Zhuo is describing the conversation with your own manager. Two levels up, the same question sounds like this.
Career question for a skip-level
"My manager and I are working on giving me more cross-functional scope. Over time, I want to lead programs that span several teams. From your perspective, what do people underestimate when they make that transition? Is there a project or person in the organization I should learn from?"
If you're ready for a formal promotion conversation, use the promotion playbook with your manager first.
Raise a problem with evidence and a clear request
A skip-level can help with a problem that crosses teams or has stayed stuck after you tried the normal channels. Explain what happened, what it cost, what you already tried, and what you want from the leader.
When a cross-team fight needs the shared boss. The player below is queued to 62:43, the exact moment Matt Mochary explains how two teams bring a stuck decision to the leader they both report up to. Watch on YouTube.
"We go to what I call the apex manager, and we go together. I share my position, you share your position, and we let them decide."
Raising a process problem
"Three launches this quarter waited more than two weeks for security review. My manager and I moved reviews earlier, but the queue remains the constraint. The delays affect the division's enterprise target. I'd value your advice on whether this needs a division-level priority decision or a different process owner."
Raising a concern about your manager
"I want advice on a pattern I've already discussed with Alex. Priorities changed four times this month after work started, and I'm having trouble getting a decision that sticks. I can share the examples and what we tried. How would you recommend I handle it?"
Use specific examples. Avoid speaking for coworkers who haven't asked you to represent them. For serious misconduct, discrimination, retaliation, or safety issues, use your company's formal reporting channel instead.
Questions worth asking your boss's boss
About the organization
- "What are the two outcomes you most need this group to deliver this year?"
- "Where do you see the greatest risk to that plan?"
- "Which decision do you wish teams would make without escalating to you?"
About your team
- "What should our team preserve as the company changes?"
- "Where could our work be more useful to the rest of the organization?"
- "What information from our level is hardest for you to get?"
About your development
- "Which skill would make me more useful on broader problems?"
- "Who handles this kind of work especially well here?"
- "What did you have to unlearn when your scope first expanded?"
Follow up without forcing a relationship
Send a short note with the point you found useful and anything you promised to do. If they offered an introduction, send them a sentence they can forward. Keep your manager informed about any next step that affects the team.
Follow-up email
"Thanks for the conversation. Your point about learning the finance side of enterprise work changed how I'm thinking about broader scope. I'm going to ask Priya if I can support the Q4 planning review, and I'll bring it up with Alex in our 1:1. I also owe you the onboarding data, which is linked here."
Frequently asked questions
Does a skip-level meeting mean something is wrong?
Usually it's just a normal way for leaders to hear from people below their direct reports. Ask your manager or the organizer for the purpose if the invitation gives no context.
Should I tell my manager what I discussed?
Share relevant work decisions and follow-ups. You don't need to give a full account. If you raised a problem involving your manager, think about confidentiality and whatever next step you agreed on with the senior leader.
Can I ask my skip-level for mentorship?
Ask for advice on a specific question first. An ongoing relationship may develop on its own, but asking a busy executive to be your mentor in a first meeting puts them on the spot.
What if I have nothing important to share?
Use the time to learn. Ask about priorities, tradeoffs, and capabilities the organization needs. A good question and a short description of your work are plenty.
The skip-level prep sheet
Before
- Ask your manager for context and share your planned topics.
- Prepare a 30-second outcome update.
- Choose one business question, one work observation, and one career question.
During
- Ask what the senior leader wants to cover.
- Connect your work to priorities above your team.
- Raise problems with examples, prior attempts, and a clear request.
- Write down advice, names, and promised actions.
After
- Send a short thank-you and anything you promised.
- Tell your manager about team-relevant actions.
- Use the advice in your next career or planning conversation.
Sources
- Lenny's Podcast: Building a Long and Meaningful Career, with Nikhyl Singhal (Jun 2023)
- Lenny's Podcast: Leveraging Mentors to Uplevel Your Career, with Jules Walter (Jan 2023)
- Lenny's Podcast: Overcome Imposter Syndrome and Accelerate Your Career, with Julie Zhuo (Jun 2022)
- Mochary Method: The Value of Issue/Proposed Solutions and RAPIDs (Mochary Method Class 3) (Nov 2021)