Skip Level Meetings — A Senior Leader's Guide

As a senior leader, you understand the importance of regular check-ins with your direct reports. But what about the individual contributors who report to them? Do you ever feel like you're out of the loop and that critical information isn't making its way up the chain?

If this sounds familiar, you may want to consider hosting skip-level meetings. Skip level meetings are one-on-one meetings between a manager of managers and the individual contributors who report to them.

These meetings can be a great way to build relationships, gain insights, and show your team members that you care about their professional development. 

Here's everything you need to know about skip-level meetings, including how to prepare and how to get the most value out of them.

What Are Skip Level Meetings and Why Are They Important to Leadership?

Skip level meetings are typically held between direct managers and the subordinates of their immediate subordinates. In other words, if you are a first-line manager, you would invite the individual contributors of your team to a one-on-one meeting. These meetings are usually informal, and they provide an opportunity for open communication between different levels of the organization.

The purpose of a skip level meeting is to allow for open communication between those in different positions within the company. This can help ensure that everyone is on the same page and that any issues or concerns can be addressed.

As the CEO or senior manager in an organization, you can use these meetings to get feedback from individual contributors about their work experiences, as well as to provide them with information about the company's direction. 

This can help you better understand the needs and challenges of those who work under you, as well as ensure that they are aware of priorities and changes in the company.

How to Prepare For Skip Level Meetings As a Leader

Step 1: Inform Your Managers or Direct Reports

The first step in starting a skip level meeting is to inform your managers. Let them know that you would like to occasionally do skip level meetings with their direct reports and why. Skip level meetings should not be a surprise to your managers, as they can be disruptive to the organization if not properly planned.

Most skip level meetings are arranged through email or by scheduling a meeting on the company’s calendar system.

Here's an email template that you can use to inform your manager of the upcoming skip level meeting:

Subject: Skip Level Meeting Request

Hi [Manager Name], 

I wanted to let you know that I would like to start something new with our team by holding skip level meetings. Skip level meetings are an opportunity for me to meet with your direct reports one-on-one, outside of the normal chain of command.
I believe that these kinds of meetings can be beneficial for several reasons:

1. I can get to know your team members better
2. I can gain insights into what's working well and what could be improved
3. I can show my team members that I'm invested in their professional development

I would like to start holding these meetings on a regular basis, perhaps once every quarter. Would you be open to letting me arrange meeting times with your direct reports? Thank you for your time!

[Your Name]

Step 2: Inform Your Skip Level Team Members

Once you have set up a meeting, it is important to inform the skip level team members. This will let them know that the meeting is happening and give them time to prepare for it. It is also a good idea to send them a copy of the agenda, so they know what to expect.

Step 3: Make Sure The Meeting Is Scheduled In a Manageable Way

The final step is to schedule the meeting in a way that is manageable for everyone involved. The most common challenge with skip level meetings is that they can be disruptive to the workday, so it is important to schedule them at a time when people are not likely to be in the middle of something else.

Breaking your meeting plan down into manageable steps will make it easier to execute and ensure that your skip level meetings are successful. Here's what you can do to make your one-on-one meetings more manageable:

1. Choose the right format

While skip level meetings can take many different formats, they are usually one-on-one meetings. However, the format you choose should be based on the goals of the meeting and the needs of your team. 

2. Set clear goals

Skip level meetings should have a clear purpose and goal. This will help you determine the best format for the meeting and ensure everyone is on the same page.

3. Prepare an agenda

An agenda will help you stay on track and ensure that all important topics are covered. With Airgram, you can create an agenda instantly with pre-built templates and share it with your team before the meeting.

How to Get the Most Value Out of Skip Level Meetings and Foster a Workplace Culture of Transparency

Skip level meetings can be an extremely valuable way to get the most value out of your time as a leader. By meeting with key players in a less formal setting, you can get a better understanding of their goals and how they're working to achieve them. You can also identify areas where you might be able to help them or where they could use your expertise.

In order to get the most value out of skip level meetings, there are a few things you can do:

1. Come prepared

In order to make the most of the meeting, come prepared with a list of questions or topics you want to discuss. This will help ensure that you make the most of the time you have together. Here are some example questions you might want to ask:

  • What are your top priorities for the next quarter?
  • What are your thoughts on the recent changes to the company's policies?
  • What challenges have you been facing in your role?
  • What projects are you working on that you're excited about?
  • If you could fix one thing about this company, what would it be?

2. Meet regularly

Skip level meetings should be scheduled on a regular basis, such as once a month. This will help ensure that you're able to stay up-to-date on each other's progress and goals.

3. Be honest

Skip level meetings are an opportunity to be honest about your work and career goals. This can be a difficult conversation to have, but it's important to be open and honest with each other in order to get the most out of the meeting.

4. Listen more than you talk

One-on-one meetings are an opportunity to learn about what's going on in other parts of the company. By listening more than you talk, you can gain lots of valuable insights. You can also use Airgram's AI assistant to record and transcribe the meeting so that even when you're not able to take notes, you can still capture everything that was said.

5. Follow up

After the meeting, be sure to follow up with the person you met with. This can be as simple as sending a thank-you note or sharing something you learned from the meeting. 


Skip level meetings are a great way to uplevel your leadership and build trust in the workplace. The insights you gain from these one-on-one meetings can help you improve all your employees, boost retention and loyalty, and increase the overall health of your organization. Skip level meetings are an important part of effective leadership, so start planning yours today!