How do you run a skip-level meeting?

Dongyoung Kim, CPO

A skip-level meeting is a one-on-one in which a leader two levels up, such as a division head, talks directly with a team member without the team lead in between. The purpose is not to evaluate the team lead but to hear about obstacles on the ground and signals in the organization that get blurred as they travel up the reporting line. Tell the team lead first, meet for 30 to 45 minutes every quarter or half year, and feed back what you hear as patterns rather than as individual comments. Keep to these three and you avoid most of the suspicion that it is a meeting held behind the team lead's back.

What is a skip-level meeting, and how is it different from a regular one-on-one?

Skip-level means skipping one level. In a division head, team lead, team member structure, a conversation between the division head and a team member is a skip-level meeting, and the team lead does not attend. The format is the same as a one-on-one, but who owns the next steps is different. For the basics of one-on-ones, start with What is a one-on-one (1on1)?.

Regular one-on-oneSkip-level meeting
WhoTeam lead and team memberSenior leader (division head, director, CEO) and team member
CadenceWeekly to every two weeksQuarterly or twice a year
Main topicsThe person's work, wellbeing, growthObstacles for the team and organization, understanding of direction, policies and processes
Who owns next stepsTeam lead and team memberThe senior leader (organization-level fixes)
Sharing with the team leadNot applicableOnly patterns that do not identify anyone

A skip-level meeting does not replace regular one-on-ones. The team member's day-to-day work and growth are still handled in one-on-ones with their team lead; the skip-level is an extra channel above that for seeing how the whole organization is doing.

Why hold skip-level meetings

  • Hear what the reporting line filters out. Each step a report passes through, it gets summarized and polished. Hearing directly from the people closest to customers tells you quickly whether a new policy or reorganization actually works on the ground.
  • Connect people to the direction directly. It is a rare chance for a senior leader to explain in person how a team member's work ties into the division's and the company's goals.
  • Find talent. You discover future team leads and hidden strengths in conversation rather than in reports.

Open a skip-level to check whether the team lead is doing a good job, and it fails. Team members hold back, the team lead turns defensive, and nobody is candid.

Cadence and format: how often, and with how many people

Skip-level meetings are commonly recommended quarterly or twice a year, depending on the size of the organization and how fast it changes. You need time to act on what you heard and to check whether the change worked (People Managing People, 2024). For the cadence of regular one-on-ones, see How often should you hold one-on-ones: weekly or every two weeks?.

  • 30 to 45 minutes per person is about right. Twenty minutes is barely enough to break the ice.
  • With more than 15 people, meeting everyone one-on-one every quarter is hard. Split them across quarters so you meet everyone at least once a year.
  • If your organization is new to this, start with small groups to set the tone, then move to one-on-ones.

Five steps to run a skip-level meeting

Whether a skip-level meeting works is decided less by the conversation than by what happens before and after it. How you tell the team lead, and how you feed back what you heard, set how candid the next meeting will be.

  1. Tell the team lead first. Before inviting team members, agree with the team lead on the purpose, schedule, and what will be shared. For example: “Starting next month I'd like to hold 30-minute skip-level meetings with people in the division every quarter. It's not to check on you; it's to hear the problems I need to solve at the division level. I'll only share patterns, without saying who said what. Let me know if there's anything you'd like me to hear from the team.”
  2. Explain the purpose to team members in advance. A sudden calendar invite from a senior leader makes people think something is wrong. Explain in a team meeting or a message why you are doing it, what you will ask, and how far it will be shared. It is even less stressful when HR announces it as a company practice rather than the senior leader.
  3. Restate the purpose and confidentiality at the start. “Today I'm here to listen. Nothing that could identify who said it will be passed on to anyone, including your team lead. The exception is anything the company must act on, such as harassment or safety, which goes through a separate process.” Stating the exception up front keeps trust from breaking later.
  4. Listen, dig deeper, and don't answer on the spot. When the senior leader talks too much, the team member just listens and leaves. When something interesting comes up, ask once more: “What exactly happened?” “Why do you think it turned out that way?” Rather than promising a fix in the room, it is safer to say, “Let me look into it and get back to you by a set date.”
  5. Turn what you heard into patterns and report back. Send a short thank-you on the day, and after each round share with everyone the common themes and what you decided about them. Open the next meeting with “Of what came up last time, this has changed and this hasn't yet.” If you only listen and nothing changes, from the second meeting on it becomes a formality.

30 example skip-level meeting questions

In a single meeting, pick only two or three of the six groups below. Try to use them all and it turns into an interview. Questions for regular one-on-ones are collected separately in What questions should you ask in a one-on-one?.

Opening questions

  • What is the most enjoyable part of your work these days?
  • What did you do before joining our team?
  • What does a typical week look like for you right now?
  • How would you score this quarter out of 10? What would have to change to make it a 10?
  • Is there anything about the team's work you think I probably don't know?

Questions to find obstacles

  • What do you find yourself waiting on most often?
  • Where do things get stuck most when working with other teams?
  • Is there a report or meeting that could disappear without anyone missing it?
  • If I could change one rule tomorrow, what should it be?
  • What are you hearing from customers a lot lately?

Questions about direction

  • If you put the division's goal for this year in one sentence, what would it be?
  • Can you see how your current work connects to the company's goals?
  • Is there a recent company decision whose reasons don't make sense to you?
  • What should our team do more of, and what could it stop doing?
  • Is there a topic I should explain more often in all-hands meetings?

Questions about working with the team lead

Avoid questions that ask the team member to evaluate their lead (“How is your team lead?”); ask about the support the team gets instead.

  • What support from your team lead helps you most?
  • Is there anything I can do to help your team lead support you better?
  • How are decisions made on the team when people disagree?
  • What would you like the team to talk about more often?
  • What would a new colleague need to know to settle into the team?

Questions about growth and career

  • What would you like to be better at a year from now?
  • Is there other work in the division you'd like to try?
  • What experience taught you the most recently?
  • What opportunity are you missing most to keep growing?
  • Are you interested in a leadership role? If so, what excites and worries you about it?

Closing questions

  • Of everything today, what is the one thing I must follow up on?
  • Is there a question I should have asked but didn't?
  • What should we talk about at the next skip-level meeting?
  • Could you sum up how today felt in a word or two?
  • If something else comes up that you want to tell me, what is the easiest way for you?

Sample skip-level meeting agenda (30 minutes)

You can paste this order straight into the calendar invite. Keep the time for sharing direction short and near the end, so it does not eat into listening.

PartTimeWhat to cover
1. Opening3 minPurpose: hearing problems to solve at the organization level What is shared: nothing that identifies anyone (exceptions: harassment, safety)
2. Follow-up from last time5 minWhat has changed since last time, and what hasn't yet
3. Listening15 minTwo or three chosen questions
4. Sharing direction4 minOne or two division priorities for this quarter
5. Wrap-up3 minWhat I will follow up on The date I will report back

How to share what you hear with the team lead

The hardest moment is when a team member voices frustration with their team lead. The senior leader should hold to three principles.

  • Don't judge from one person's words. Note what came up once, and treat it as a pattern only when several people say something similar.
  • Tell the team lead about the impact, not the incident. Instead of “A said they were upset in a meeting,” say something that does not reveal who it was, such as “Several people find the frequent priority changes hard.” On a small team of two or three, wait two or three rounds before sharing so no one can be identified.
  • Solve it with the team lead. If the senior leader bypasses the team lead and fixes a team member's problem directly, team members will start bypassing the team lead too. Decide on improvements together with the team lead, and let the team lead bring them to the team.

When sharing with the team lead, a summary like this works.

This quarter's skip-level summary (Team X, 4 people)Details
Going wellSeveral people said the weekly priority update helps
Recurring obstacleSchedules slip while waiting for other teams' reviews
Division willSort out the review request channel (owner: division head, by Dec 15)
To look at with the teamPeople find it hard to speak up in meetings

Anything the company must act on, such as workplace harassment, discrimination, safety, or legal issues, should not wait for a pattern: take it to HR right away under your company's procedures.

Five common skip-level meeting mistakes

MistakeWhy it is a problemDo this instead
Scheduling without telling the team leadThe team lead feels watched, and the team member thinks something is wrongBrief the team lead, then the whole team, then send individual invites
The senior leader does most of the talkingA listening session turns into a speechKeep sharing direction to the last five minutes
Promising a fix on the spotBroken promises erode trust at the next meetingAnswer, “I'll check and get back to you by a set date”
Asking questions that evaluate the team leadTeam members clam up or end up playing evaluatorAsk about the support and obstacles the team has
Doing it once and stoppingNothing visibly changes, so next time no one speaks upSet a quarterly or half-yearly cadence and always start with follow-up from last time

If you are in HR, skip-levels are steadier as a company practice than as an individual leader's habit. Writing down the purpose, cadence, and sharing rules and trying them in a pilot division first follows the same process as How do you roll out a one-on-one program? Six steps for HR.

Frequently Asked Questions

Q.How often should skip-level meetings happen?
Once a quarter or once every six months is typical, because you need time to act on what you heard and check the result. If there are many people, split them across quarters so you meet everyone at least once a year.
Q.What if the team lead is uncomfortable with skip-level meetings?
Promise up front that the purpose is not to evaluate them and that you will share only patterns. When you give the team lead a useful summary after the first round, they are more likely to see skip-levels as support rather than surveillance.
Q.What if a team member complains about their team lead?
Listen to the end and note the specific situation and its impact, but don't judge or promise anything in the room. If it comes up from several people, raise it with the team lead in your one-on-one without revealing who said it, and send matters such as harassment straight to HR's process.
Q.Can I take notes in a skip-level meeting?
Yes, but tell the team member at the start what you will record and how far it goes. If you record audio, always get consent first, and limit who can read the notes to the senior leader and the HR staff who need them.
Q.How is a skip-level meeting different from a town hall?
A town hall is where a leader explains direction to many people and takes questions; a skip-level is where you listen in depth to a few. Hear in skip-levels what rarely comes up in a town hall, then share the results back at the town hall, and the two complement each other.

ORBLIT

How Orblit helps

To make it easier to put this article into practice, Orblit helps in these ways.

  • 01Pick up from last time, even a quarter later

    With skip-levels only once a quarter, memory is not enough. Record the conversation and AI organizes it into a summary and action items, which carry over into preparing the next meeting.

  • 02Only the people who need it can read it

    Each workspace's data is kept separate and access is managed by role, so skip-level notes can be limited to the people who need them.

  • 03Recordings are not kept

    Meeting data is not used to train AI models, and recordings are deleted automatically within three days after analysis.

Sources

  1. Skip-Level Meetings: A Comprehensive Guide With Process · People Managing People (Karen Weeks) · 2024-11-01

Read next

What is a one-on-one (1on1)?

A one-on-one (1on1) is a formal, two-way conversation in which a leader and a team member meet one-to-one at a set time to talk about work and growth. Unlike a status report or a casual lunch chat, it has a set time and purpose, and the leader listens to the team member instead of simply giving instructions. It repeats on a short cycle of roughly one week to one month rather than twice a year or once a year, and it focuses on managing the process and supporting growth rather than on results.

Dongyoung Kim, CPO

What questions should you ask in a one-on-one?

Pick one or two one-on-one questions from five topics: wellbeing, work, growth, feedback, and team. Rather than asking everything at once, start with the topic the team member most wants to discuss, and after hearing the answer add a question that leads to a next step, such as "What support would help?" The questions below are examples compiled by Orblit.

Dongyoung Kim, CPO

How do you roll out a one-on-one program? Six steps for HR

Roll out a one-on-one program by setting its purpose and minimum standards, having executives and a pilot team experience it first, and then extending it company-wide. A single leader training and a distributed guideline are not enough: when things get busy, one-on-ones are the first thing dropped. HR's role is not to hold the conversations but to create the standards, tools, and learning that let leaders hold them consistently. Measure the effect by what changed after the conversations, not by completion rates.

Dongyoung Kim, CPO