If you manage other managers, holding skip-level one-on-one meetings with their direct reports is paramount. Here’s how to do ’em.

If youâre a manager of managers, skip-level meetings are your lifeline. I donât mean to sound bombastic, but if youâre a CEO, executive, or director who manages other managersâââthen skip-level meetings are an essential way to keep your ears on the ground.
Skip⌠what? If youâre anything like me, when I first heard the term âskip-level meeting,â I was befuddled. Yes, I held one-on-one meetings with my team. But as the team grew and I had a manager who had someone else reporting to them⌠I wasnât talking to their direct report with any regularity. How was I supposed to ever learn what that team member was thinking and feeling about the company if I never talked with them?
As a leader, itâs easy to become isolated in your ivory tower. As Nandan Nilekani, co-founder of Infosys was once quoted:
âIf youâre a leader, you can put yourself in a cocoon-a good-news cocoon.â
When youâre at the top, youâre the last to know that a significant number of team members disagree with the strategy. Or, youâre the last to know that someone critical to the company is thinking about leaving the company. The bad news is diluted before it reaches your vantage pointâââor, itâs all together shuttled out of your sight.
So, how do you get out of this cocoon?
Skip-level meetings are one answer.
Based on insights from our online leadership community, and the 15,000+ people who use Know Your Team, hereâs everything you need to know about what skip-level meetings are if you need them, and how to run them well.
What is a skip-level meeting?
A skip-level meeting is a meeting where you, as a manager, meet one-on-one with the direct report of a manager who you manage. Hence, the âskipped level.â For example, if you have 5 managers who directly report to you, and there are 45 employees who then report to them, the skip-level meetings would be the ones youâd hold with any of those 45 employees. Itâs a variant of the one-on-one meeting you might already be doing with your direct reports.
For you as a manager, the purpose of a skip-level meeting is to get out of your good news cocoon: How are folks on the team really feeling about the work, the culture, and the team around them. What could be better? What needs to be resolved? Itâs valuable, sacred time that you truly wonât get anywhere else.
Skip-level meetings are dually beneficial for the employee, as well. Itâs an opportunity for them to get aligned and centered around the visionâââand ask you valuable questions that help them with their own work.
How often, for how long?
One of the first reactions you might have to a skip-level meeting is: âWait for a second, how am I logistically supposed to meet with all these people?â
Itâs possible đ
In our online leadership community, one manager remarked how she regularly holds skip-level meetings with 60 employees every quarter. For another manager, she had 20 employees they held skip-level meetings with, whom she would also meet with once a quarter. Now, this doesnât mean you have to do hold them all in one three week time chunk (you could spread them out a few days a week across a quarter)âââwe all have limited bandwidth and calendar space! But it does mean, if you want to prioritize the perspective of your team, that should be reflected on your calendar.
As you decide how often to hold these skip-level meetings, consider:
- If you care about understanding the state of your team, what feels like the right frequency to be listening to happening whatâs âon the groundâ? Can you set aside 1 week every quarter to hold all your skip-level meetings? What feels both doable and responsible to you?
- If, logistically-speaking, not meeting with everyone once a quarter will work, can you at least meeting with folks bi-yearly? How about once a year? Or, can you share the load with your co-founder or another executive team member so all employees have at least one skip-level meeting per year?
One size doesnât fit all. Adjust the frequency of these skip-level meetings as you have them, as you learn what best fits your team. You also donât want to overdo the frequency of skip-level meetings: After all, the employees are reporting to your managersââânot to you. They should be meeting most frequently with their managers and not with you.
Generally, you want to set aside an hour for your skip-level meeting, so you have ample time to get into issues and cover topics you might not typically discuss. However, a few managers in our community have shared how 30 minutes can work if there is a very focused agenda. Personally, I recommend setting aside one hour so no one feels rushed. The last thing you want to do is create an environment for the employee where they feel like youâre eyeing the clock.
Almost all managers Iâve talked to who hold skip-level meetings hold them with everyone in their team. This is for a few reasons: First, youâll gain the widest breadth of perspectives by talking to all the employees who report to your managers. Second, you wonât encourage any sentiments of unfairness or that you have a specific agenda in talking to only âsomeâ people in your team.
How do you start having skip-level meetings?
One of the most crucial parts to skip-level meetingsâ success is how you kick them off. As you might imagine, if your managerâs direct report all of sudden receives a calendar invite from you for a meeting without any context, they might panic. Whatâs wrong? Did they mess something up? Are they going to get fired?
Equally important is to tell the managers who report to you that youâd like to start holding skip-level meetings. You donât want them to feel youâre undercutting them, or have any hidden agenda in wanting to talk with their direct reports. Rather, make it clear that itâs part of a genuine effort to make sure youâre being the best leader you can beâââand itâs a way for the employee to feel more integrated within the company.
Hereâs a template for what you could write to your manager, about starting skip-level meetings with their direct reports:
Hey [YOUR MANAGERâs NAME],
Lately, Iâve been doing a lot of deep thinking about what I can do to become a better leader. And I was considering that having regular skip-level meetings might be a helpful way for me to try to become a better leader to themâââand a better leader to you.
Hereâs how it might workâŚ
Once a quarter, with your permission, Iâd set aside 45 minâââ1 hour to chat with each of your direct reports. The agenda would include questions like, âCould I be doing a better job outlining the vision and direction for where weâre headed?â and âWhen have you felt most proud about being a part of the company this past year?â And theyâll have a chance to ask me other questions, too.
Hopefully, itâll be an opportunity to create greater alignment about our vision and provide a chance for them to weigh in on higher level leadership topics that affect the organization.
Curious what you think? I was thinking of kicking them off on [INSERT DATE]. Open to any input you might have on the idea, timing etc.
Warmly,
[YOUR NAME]
Hereâs a template for what you could write to your managerâs direct reports, about starting skip-level meetings with them:
Hey [EMPLOYEEâS NAME],
Lately, Iâve been doing a lot of deep thinking about what I can do to become a better leader. And I was considering that having regular skip-level meetings might be a helpful way for me to try to become a better leader to you.
Hereâs how it might workâŚ
Once a quarter, with your go-ahead, Iâd set aside 45 minâââ1 hour to chat with you. The agenda would include questions like, âCould I be doing a better job outlining the vision and direction for where weâre headed?â and âWhen have you felt most proud about being a part of the company this past year?â Iâd send an agenda ahead of time that Iâd love to get your input onâââso youâll definitely have a chance to ask me anything thatâs on your mind too.
Hopefully, itâll be an opportunity get more centered around our vision together, and give us some time to think through what is working and isnât working at the company.
Curious what you think? I was thinking of kicking them off on [INSERT DATE]. Open to any input you might have on the idea, timing etc.
Warmly,
[YOUR NAME]
How to prepare for a skip-level meeting?
In a survey we conducted last year with 1,182 managers and 838 employees about one-on-one meetings, we found 36% of employees believe their manager is only âsomewhat preparedââââand 40% of employees think their manager is ânot preparedâ or ânot prepared at all.â
Sheesh. We have some improvement to do here, as managers, when it comes to preparing for one-on-one meetings! The same is true when it comes to skip-level meetings.
Before your skip-level meeting, take 15 minutes to do the two following things:
#1: Get up-to-speed.
Your skip-level meeting should not be spent getting caught up on the employeeâs latest project. You can read about that in Slack, Basecamp, Trello, etc. So any time you spend asking âWhatâs the latest on X?â youâve wasted invaluable time in your skip-level meeting. Instead, review status updates ahead of time.
#2: Co-create an agenda.
Spend time brainstorming 5â7 questions that you want to ask the employeeâââand then send the agenda over to the employee to get their input and have them add any questions theyâd like.
On your end, at least one of the agenda questions should be something that helps establish trust or rapport in the beginning, to help your employees feel more comfortable before diving into the conversation. The rest of the questions should be focused on either feedback, issues/concerns in the company, and/or career direction. Lastly, youâll then want to leave 10 or so minutes at the end of the agenda to discuss the next steps and takeaways.
Hereâs an example of a skip-level meeting agenda:
Personal connection (10 minutes) Concerns/Issues (20 minutes)
- As a company, do you think weâre behind the curve on anything in particular?
- When have you been disappointed with a decision or the direction that the company has gone in the past quarter?
- What rumors are you hearing that you think I should know about?
Feedback (20 minutes)
- When have you felt most proud of being a part of the company this past year?
- Could I be doing a better job outlining the vision and direction for where weâre headed?
Takeaways / next steps (10 minutes)
What to NOT do in a skip-level meeting.
Skip-level meetings can be tricky navigate, as youâre not the person directly managing the person who youâre talking to. You want to make sure youâre not undercutting your manager or overstepping your bounds. You want to give your manager space to be a manager to their own direct report. While you might be ultimately running the entire team, department, or organization, itâs their direct reports, not yours. Here are a few things to keep in mind to not do during your skip-level meetings:
- Donât make decisions. Your manager should make decisions in accordance with their domain and scope. You may unintentionally undermine them if you make immediate decisions in that skip-level meeting without consulting them.
- Donât problem-solve. The best leaders donât solve problems themselvesâââthey help their team solve problems. I wrote a piece here on the questions you can ask instead if you find yourself feeling compelled to solve a problem during a skip-level meeting.
- Donât escalate. If something springs up that is surprising or downright shocking, resist the urge to immediately escalate it and tell the person, âIâm going to take this to so-and-soâŚ.â Rather, thank the person for the feedback and give yourself some time outside the skip-level meeting to calibrate what might be the best responses. Reactive moments, in the moment, are rarely productive nor the most thoughtful course of action.
- Donât refute. The surest way to dissuade the employee that youâre not truly open to feedback is if you right away jump to refuting their point. âWell, hereâs why thatâs the caseâŚâ or âLet me tell youâŚâ is the natural, instinctive response, but it comes across as being defensive. Instead, try these five techniques for receiving negative feedback well.
During a skip-level meeting, you âput your listening ears onâ as Pooja Brown, VP of Platform Engineering at Stitchfix, has described on our Heartbeat Podcast. Youâre coming from a place of empathy and attempting to collect more data for you to weigh on laterâââyouâre not trying to make the call, now. Youâre in âlearning modeâ to incorporate insights into your own decision-making.
As a result, youâll want to prepare ahead of timeâââco-creating an agenda and asking specific and thoughtful questionsâââand, hold these skip-level meetings regularly to unearth meaningful insights about whatâs going on in your team at the direct report level.
Only with that mindset, approach, and preparation can you emerge from the âgood news cocoonâ weâre trapped in as leaders. Start with these best practices for skip-level meetings here.
âĄď¸Want a helpful hand for running your skip-level meetings? You might want to peek at our Training Program. It gives you hundreds of questions and one-on-one meeting templates, just like the ones here, that are applicable for skip-level meetings.