Skip level meetings: What they are, and exactly how to run them

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 you’re a manager of managers, skip level meetings are your lifeline. I don’t mean to sound bombastic, but if you’re a CEO, executive, or director who manages other managers — then skip-level meetings are an essential way to keep your ears on the ground.

Skip… what? If you’re anything like me, when I first heard the term “skip level meeting,” 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 wasn’t 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, it’s easy to become isolated in your ivory tower. As Nandan Nilekani, co-founder of Infosys was once quoted:

“If you’re a leader, you can put yourself in a cocoon-a good-news cocoon.”

When you’re at the top, you’re the last to know that a significant number of team members disagree with the strategy. Or, you’re 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 point — or, it’s 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 The Watercooler, our online leadership community with 1,000+ managers from all over the world, and the 15,000+ people who use Know Your Team’ s One-on-One Meetings tool, here’s 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 “skipped level.” 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 you’d hold with any of those 45 employees. It’s 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? It’s valuable, sacred time that you truly won’t get anywhere else.

Skip level meetings are dually beneficial for the employee, as well. It’s an opportunity for them to get aligned and centered around the vision — and 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: “Wait for a second, how am I logistically supposed to meet with all these people?”

It’s possible 🙂

In our online leadership community, The Watercooler, 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 doesn’t 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) — we 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 what’s “on the ground”? 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 doesn’t fit all. Adjust the frequency of these skip-level meetings as you have them, as you learn what best fits your team. You also don’t want to overdo the frequency of skip-level meetings: After all, the employees are reporting to your managers — not 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 The Watercooler 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 you’re eyeing the clock.

Almost all managers I’ve talked to who hold skip-level meetings hold them with everyone in their team. This is for a few reasons: First, you’ll gain the widest breadth of perspectives by talking to all the employees who report to your managers. Second, you won’t encourage any sentiments of unfairness or that you have a specific agenda in talking to only “some” people in your team.

How do you start having skip-level meetings?

One of the most crucial parts to skip-level meetings’ success is how you kick them off. As you might imagine, if your manager’s direct report all of sudden receives a calendar invite from you for a meeting without any context, they might panic. What’s wrong? Did they mess something up? Are they going to get fired?

Equally important is to tell the managers who report to you that you’d like to start holding skip-level meetings. You don’t want them to feel you’re undercutting them, or have any hidden agenda in wanting to talk with their direct reports. Rather, make it clear that it’s part of a genuine effort to make sure you’re being the best leader you can be — and it’s a way for the employee to feel more integrated within the company.

Here’s a template for what you could write to your manager, about starting skip-level meetings with their direct reports:

Hey [YOUR MANAGER’s NAME],

Lately, I’ve 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 them — and a better leader to you.

Here’s how it might work…

Once a quarter, with your permission, I’d set aside 45 min — 1 hour to chat with each of your direct reports. The agenda would include questions like, “Could I be doing a better job outlining the vision and direction for where we’re headed?” and “When have you felt most proud about being a part of the company this past year?” And they’ll have a chance to ask me other questions, too.

Hopefully, it’ll 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]

Here’s a template for what you could write to your manager’s direct reports, about starting skip-level meetings with them:

Hey [EMPLOYEE’S NAME],

Lately, I’ve 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.

Here’s how it might work…

Once a quarter, with your go-ahead, I’d set aside 45 min — 1 hour to chat with you. The agenda would include questions like, “Could I be doing a better job outlining the vision and direction for where we’re headed?” and “When have you felt most proud about being a part of the company this past year?” I’d send an agenda ahead of time that I’d love to get your input on — so you’ll definitely have a chance to ask me anything that’s on your mind too.

Hopefully, it’ll be an opportunity get more centered around our vision together, and give us some time to think through what is working and isn’t 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 “somewhat prepared” — and 40% of employees think their manager is “not prepared” or “not prepared at all.”

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 employee’s latest project. You can read about that in Slack, Basecamp, Trello, etc. So any time you spend asking “What’s the latest on X?” you’ve wasted invaluable time in your skip level meeting. Instead, review status updates ahead of time. (We have a Heartbeats feature in Know Your Team that makes it incredibly easy for everyone in a team to know what everyone else is working.)

#2: Co-create an agenda.

Spend time brainstorming 5–7 questions that you want to ask the employee — and then send the agenda over to the employee to get their input and have them add any questions they’d like. (You can use Know Your Team ‘s One-on-Ones tool to do this, in fact!).

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, you’ll then want to leave 10 or so minutes at the end of the agenda to discuss the next steps and takeaways.

Here’s an example of a skip level meeting agenda:

Personal connection (10 minutes) Concerns/Issues (20 minutes)

• As a company, do you think we’re 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 we’re headed?

Takeaways / next steps (10 minutes)

You can use Know Your Team’s One-on-Ones feature to get agenda templates just like this and hundreds of questions for your skip-level meetings. Additionally, we make it really easy for you and your direct report to collaborate on an agenda together. (You can sign-up to give the One-on-Ones tool a spin, here, if you haven’t already. )

What to NOT do in a skip level meeting.

Skip level meetings can be tricky navigate, as you’re not the person directly managing the person who you’re talking to. You want to make sure you’re 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, it’s their direct reports, not yours. Here are a few things to keep in mind to not do during your skip-level meetings:

• Don’t 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.
• Don’t problem-solve. The best leaders don’t solve problems themselves — they 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.
• Don’t escalate. If something springs up that is surprising or downright shocking, resist the urge to immediately escalate it and tell the person, “I’m going to take this to so-and-so….” 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.
• Don’t refute. The surest way to dissuade the employee that you’re not truly open to feedback is if you right away jump to refuting their point. “Well, here’s why that’s the case…” or “Let me tell you…” 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 “put your listening ears on” as Pooja Brown, VP of Platform Engineering at Stitchfix, has described on our Heartbeat Podcast. You’re coming from a place of empathy and attempting to collect more data for you to weigh on later — you’re not trying to make the call, now. You’re in “learning mode” to incorporate insights into your own decision-making.

As a result, you’ll want to prepare ahead of time — co-creating an agenda and asking specific and thoughtful questions — and, hold these skip-level meetings regularly to unearth meaningful insights about what’s going on in your team at the direct report level.

Only with that mindset, approach, and preparation can you emerge from the “good news cocoon” we’re trapped in as leaders. Start with these best practices for skip level meetings here.

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⚡️Want a helpful hand for running your skip-level meetings? You might want to peek at our One-on-Ones Tool in Know Your Team. It gives you hundreds of questions and one-on-one meeting templates, just like the ones here, that are applicable for skip level meetings – so you no longer have to copy ‘n paste these one-on-one questions from our blog posts 😉 Check out Know Your Team out for holding your skip-level meetings here.

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Claire is the CEO of Know Your Team – software that helps you avoid becoming a bad boss. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.