How to Use Skip-Level Meetings Effectively

Last updated: August 30, 2021
Estimated reading time: 4.5 min


Purpose of Skip-Level Meetings

Skip-level meetings are one-on-one meetings that managers hold with staff other than the people they manage directly. In most small- or mid-sized organizations, these are typically meetings with the direct report(s) of the people that you manage. In large hierarchical organizations, there might be multiple layers between you and the person you’re meeting with. (From now on, we’re going to refer to the manager that you manage as “the manager” and the person they manage as “the staff person.”)

They are helpful for:

  1. Building relationships with people on your team who don’t directly report to you.
  2. Gaining valuable insight into your team and organization.
  3. Getting feedback about the managers that you manage (or about yourself!).

Assuming that your organization has a traditional, hierarchical structure, if you manage managers, you probably have a fair amount of positional power. You may also have other types of power and privilege relative to the staff person. Skip-level meetings are a way to leverage the power you have to build trust, invite a diversity of perspectives, and gather information that helps you be more strategic and accountable in your decision-making.

Anatomy of a Skip-Level Meeting

There are tons of variables that determine the exact agenda of a skip-level meeting, but the basic components are the same whether it’s your first time or your tenth time.

1. Set the tone.

Meeting with your boss’s boss can feel like being called into the principal’s office. Alleviate any anxiety and dispel assumptions by sharing the purpose of the meeting (if it’s your first skip-level with this person, share why you do skip-level meetings, in general). Be clear about what you’re not looking to get out of it (such as decision-making or problem-solving). Share how you will use the information gathered in the meeting (including who else, if anyone, you’ll share it with).

2. Connect.

This part isn’t rocket science—get curious and deepen your personal connection. You don’t need to learn their life story, but ask questions to better understand where they come from and what motivates them. If you have specific praise to share, this is a good time to do it.

3. Invite their insight and/or feedback.

For many of you, this is where you might spend most of your time in this meeting. Get their perspective on how things are functioning at the organization and how they’re being managed. The staff person might be reluctant to be fully honest, so do your best to help them feel at ease. Remember to stay in listening mode. Resist the urge to problem-solve, defend, refute, or explain unless you are explicitly asked to. It can take a lot of courage to share insights that may go against the norm or to raise concerns. Even if you don’t agree or understand, make sure to appreciate them for their honesty.

4. Open it up.

Ask if there’s anything else they’d like to discuss.

5. Wrap up.

Thank them for their time, share your next steps, and restate how you plan to use the information. If they raised concerns about their manager, encourage them to address those issues directly if it makes sense to do so. Lastly, share a specific appreciation for their contributions to the team.

Questions to Ask

Purpose Sample Questions
Building connection/rapport
  • What brought you to this role/team/organization?
  • What’s your favorite thing about _____ (your job/the city/being a parent/the place that you’re from)?
  • What’s something new you’ve been doing outside of work?
  • What’s something that has inspired you recently? Why?
Information/feedback gathering on manager
  • What’s the best part of working with <their manager>? What’s the hardest part?
  • What do you wish <their manager> would do more or less of?
  • What’s a recent situation that you wish your manager had handled differently?
  • How effectively do you feel your manager is at managing you—providing support, holding you accountable, and building a relationship with you?
  • How effectively do you feel your manager navigates lines of power and difference?
Information/feedback gathering on organization
  • If you could fix any process, what would it be and why?
  • Which organizational value do you think we’re living every day? Which one do you think we need to get better at?
  • What’s something about our organizational culture that you love? What’s something you want to do away with?
  • If you were in charge, what’s one thing you would do differently here?
  • When in the last year have you felt disappointed or concerned about a leadership decision?
  • What’s something you’ve observed in your role that you think I might not be seeing in my position?

Tips for Implementing Skip-Level Meetings

Meet with everyone.

This is a prix fixe menu, not a buffet—it’s not fair to pick and choose which of your skip-level team members to meet with. If you absolutely can’t meet with everyone in a time period, remember that this is a choice point. Think about the most equitable choice you can make.

Don’t hide the ball.

Tell your managers that you’ll be meeting with their direct reports. Tell the staff members why you will be meeting with them and what they can expect (see our template emails on the next page).

Aim for meeting twice a year with each person.

If you only have a handful of people to meet with, you may want to consider doing this quarterly.

Schedule 15 minutes post every skip-level meeting.

Take time to synthesize the conversation, capture trends, and decide on next steps.

Ready to get started? Check our Skip-Level Meeting Sample Emails for informing managers and staff.

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