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One of the main challenges of becoming a manager of managers is maintaining a human connection with each person on your team. 

“When you get to a team size of 60, 70, or 80, people start to look more like pieces on a board rather than humans,” says Jason Wong – a leadership coach and former senior director of engineering at Etsy. “You find yourself wanting to spend more time alone, away from people. And, while that might make your job feel easier, I think we have an obligation to never lose touch with the human cost of our decisions.”

Skip level one-on-one meetings are the best tool for senior managers, directors, VPs, and CEOs to understand the team’s culture and get to know the people that work in the company. 

Just like regular one-on-one meetings (where managers meet with their direct reports), skip-level meetings are a great way to foster communication and build rapport. 

“Over the years, I gained a lot of insights from my skip-level 1-1s that helped me make better choices,” says Wong. “But, more importantly, in the end skip-level 1-1s kept me connected to my organization in ways that made me a better, more human leader.”

What is a skip-level meeting?

Skip-level one-on-ones are meetings where upper-level leaders “skip” middle-level management to talk directly to the people that work two levels away from them. 

In other words – if your direct report manages a team, you would be meeting with that person’s direct reports. 

The benefits of skip-level meetings

According to Wong, skip level one-on-one meetings can help you build stronger relationships with your organization, understand how managers on your team are performing, and gain first-hand accounts on how your decisions affect people in the company.

Some other benefits of skip-level one-on-one meetings include:

– Understanding how people across your team feel about their work.

– Getting feedback to improve the way you communicate the team’s vision.

– Building trust and rapport with employees that don’t report directly to you.

– Encouraging transparency and open communication across all levels.

– Helping managers develop and become better leaders.

What’s inside this skip-level meeting template:

Here are 7 questions that will help you connect with employees and learn how to better support their managers through skip-level one-on-one meetings:

1 Are you happy in your role? What could make it better for you?

Asking people this question shows that you care personally about them. As Russ Laraway, Chief People Officer at Qualtrics described at the First Round CEO summit:

“One way to know if you’re exhibiting service leadership is if the people under you are growing and developing.”

That’s why an important part of your skip-level one-on-ones is understanding if people enjoy going to work – and what steps can their managers take to increase that engagement.

Inevitably, you’ll end up hearing about someone’s struggles and will want to do something about it. However, As Jason Wong argues, you should never “preempt” the manager. Instead, try to coach employees on how they could address the issues and make sure to communicate the outcomes of the discussion with their manager:

“I usually try to help folks advocate for themselves by coaching them on how to effectively communicate the issue to their manager,” says Wong. “Afterward, you might want to give your manager a heads up that their report is going to be approaching them about an issue.” 

2 When have you felt most proud about being a part of the company?

This question will help you understand what types of projects and work motivate each person. Asking about their “proud moments” is not only a great way to learn more about their interests but to thank them personally for their hard work. 

“You will have a deeper familiarity with their work, interests, and ambitions,” says Wong. “And, when stretch assignments or opportunities arise, you will have more information with which to make decisions and influence outcomes.”

If you know about a project where the person was involved, this is the perfect time to show them your appreciation.

Camille Fournier suggests a similar third question in The Manager’s Path:

– What do you like best about the project that you are working on?

Regardless of the question you choose, make sure you show an interest in the type of work that excites each person, and the moments in the company that they feel most proud about.

3 What’s one thing we should start, stop, and continue doing as a team?

The truth is, when you are a senior manager, director, or CEO, people won’t want to come to you with feedback or bad news. As Nandan Nilekani, co-founder of Infosys argues in a Harvard Business Review article, it’s easy to put yourself in a good-news cocoon:

“If you’re a leader, you can put yourself in a cocoon – a good-news cocoon. Everyone tells you, ‘It’s all right—there’s no problem.’ And the next day, everything’s wrong.”

That’s why, if you want to understand what needs to change in the company, you need to go outside your office and ask the team personally. Here are two similar questions that Camille Fournier suggests in The Manager’s Path:

– What changes do you think we could make to the product / team / company?

– How do you think the organization is doing overall? Anything we could be doing better / more / less?

And what if you don’t fully agree with the feedback? Julie Zhuo (author of The Making of a Manager) suggests thanking employees for the courage to criticize you, the company, or their manager:

“Even if you don’t agree with what’s said, receive it graciously and recognize that it took effort to give. If others find you defensive, you’ll get less feedback in the future, which will only hurt your growth,” says Zhuo.

4 What do you find unclear about our strategy and vision?

Having a team strategy is essential to your success, but even more important than that is making sure that the team understands it.

In the book The Ride of a Lifetime, Robert Iger (CEO of The Walt Disney Company) argues that conveying priorities clearly and repeatedly is what separates great leaders from the rest:

“If leaders don’t articulate their priorities clearly, then the people around them don’t know what their own priorities should be. Time, energy, and capital get wasted,” says Iger. “People in your organization suffer unnecessary anxiety because they don’t know what they should be focused on. Inefficiency sets in, frustration builds up, morale sinks. You can do a lot for the morale of the people around you, and therefore the people around them, just by taking the guess-work out of their day-to-day life.”

Skip-level meetings are a great opportunity to eliminate that guess-work.

By asking your teammates if there are any areas of the business strategy that aren’t very clear, you’ll be able to clarify any open doubts and understand if you could be doing a better job at explaining the overall strategy and vision.

5 What’s the best part of working with <their manager>?

Now, before the meeting ends, make sure to ask a couple of questions about that person’s manager (your direct report). 

According to Kim Scott, author of Radical Candor, the purpose of skip-level meetings is to create a culture where everyone feels comfortable giving feedback directly to their boss.

“This meeting is a step in that direction,” says Scott. “Not a substitute for that goal.”

Start by asking what they like about working with them – this will give you some great insights on that person’s leadership abilities and strengths.

If you hear something great, make sure to let your direct report know and congratulate them for their work.

“Generally, it’s easiest to start with praise to get people talking,” says Scott. “‘What is your manager doing well?’ Then, ‘What could your manager be doing better?’ Then, ‘What really sucks?’”

6 What do you wish <their manager> would change/do more of?

Before asking for constructive criticism about their manager, let employees know that the meeting is “not for attribution.” In other words:

“Everything of import will be shared with their boss, but not who said it,” says Scott.

As feedback emerges, make sure to take note of what people say and encourage them to let you know if something you wrote seems inaccurate. According to Scott, this is the best way to catch misunderstandings.

Finally, thank people for the honesty and courage to criticize their boss, and coach them on how to address the feedback with their manager:

“Try to get people to think about solutions, so it doesn’t devolve into a gripe session,” says Scott. “But if you’re getting a lot of complaints, remind yourself it is a good thing not a bad thing. You are failing only if it is all sweetness and light.”

7 What’s your favorite book, podcast, or movie?

Last but not least, end the discussion in a friendly manner. 

You can do this by asking the employee something about their life outside of work, such as what they enjoy doing in their spare time, what book they are reading, or what type of podcasts they enjoy listening to. Use the last minutes of the meeting to get to know the person on a personal level and build rapport.

As Kim Scott argues in Radical Candor:

“At the very heart of being a good boss is a good relationship.”

Skip-level meetings: How often should you schedule them?

We know what you might be thinking: 

“Meet with my direct report’s reports? That sounds like a lot of meetings!”

But don’t panic. You don’t have to meet with everyone during the same week. In fact, some leaders like to spread out their skip-level meetings across the quarter (or the year, depending on the size of their team)

“You might find it helpful to be systematic with skip level 1:1s and work to meet each of your skip level folks once-per month/quarter/year depending on the size of your organization,” says Steven Sinofsky – former president of Windows and a partner at Andreessen Horowitz. “If you manage a team of 100, it should be possible to have a skip level with every member of the whole team yearly. More than that and you will probably want to structure your skip-levels to include only your directs of directs, perhaps every six months.”

Before you go and schedule those calendar events (which should last between 45-60 minutes), here’s one last thing you need to do – tell your direct reports about this initiative:

“If you are conducting a skip level meeting, sit down with the manager of the team first,” says Scott Boulton – an HR advisor. “Explain to them why you are looking to conduct the meeting, what you are going to ask and what you will do with the information you obtain. You need to get the manager’s buy-in.”

Once you let your managers know that the purpose of skip-level meetings is to open up the lines of communication within your department, the second step is to explain this new type of meeting to the entire team. You could do this by including a short description in the calendar event:

“Receiving an unexpected meeting invite from a Director can produce anxiety. You may not feel important, but that doesn’t mean folks don’t view you as such,” says Wong. “Be clear about your intent. I framed my 1-1s as time for engineers to share with me how things were going, what was worrying them, and how we could get better together.”’