A skip-level meeting is one of the most effective ways for senior leaders to build trust, strengthen relationships, and gain valuable insights from employees who don’t report to them directly. These meetings offer an opportunity to break down communication barriers, gather honest feedback, and align teams around shared goals.
But preparing for a skip-level meeting—whether you’re a manager or a staff member—requires more than just showing up. It means setting clear expectations, asking the right questions, and following up on next steps.
In this guide, we share advice on how to conduct a skip-level meeting that fosters open communication, drives engagement, and helps you avoid common pitfalls. This resource will equip you with actionable strategies to make every skip-level meeting a success, from how to build a strong agenda to the best questions to ask your skip-level employee.
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What is a Skip-Level Meeting?
A skip-level meeting is a structured one-on-one meeting between a manager and a staff person that they don’t 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 larger organizations, there might be multiple layers between you and the staff person. (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.”)
Assuming that your organization has a traditional, hierarchical structure, if you manage managers, you probably have positional power. You may also have other types of power and privilege relative to the staff person, and having this feedback meeting with your staff can help you gain new perspectives.
Skip-level meetings are a way to leverage the power you have to build trust, invite more diverse perspectives, be more strategic and accountable in your decision-making.
Why Are Skip-Level Meetings Important?
Skip-level meetings benefit everyone—leaders, managers, and staff. They help you:
- Build relationships with team members who don’t directly report to you.
- Gain valuable insight into your team and organization.
- Get feedback about the managers that you manage (or about your own leadership!).
- Increase employee engagement and retention.
- Identify “rising stars” among your staff.
How to Prepare for a Skip-Level Meeting
Preparation is key for impactful and productive skip-level meetings. Here’s how you can prepare:
- Communicate intent: Share the meeting’s purpose and goal—building relationships, gathering insights, and fostering transparency. You can start with an email (see samples on this resource).
- Share sample questions: Share some of the questions you might ask so that the staff person can prepare.
- Familiarize yourself with their work: Refresh yourself on their role expectations, key projects, and goals.
How to Conduct a Skip-Level Meeting
You should always tailor a meeting agenda to your context and relationship, but there are a few basic components for every skip-level.
Set the tone
Meeting with your boss’s boss can feel like being called into the principal’s office. Alleviate 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. 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 they share in the meeting (including who else, if anyone, you’ll share it with). Your goal is to help the staff person feel at ease.
Build rapport and connect
Get curious and deepen your personal connection. You don’t need to learn their life story, but try to better understand where they come from and what motivates them. If you have praise to share, do it!
Invite their insight and feedback
For many of you, this is where you might spend most of your meeting time. Get their perspective on how things are going at the organization. Ask them to share feedback about how they’re being managed. Unless you’re asked for an explanation or problem-solving support, stay in listening mode. It can take a lot of courage to raise concerns, so if they do, appreciate them for their honesty.
Open it up
Ask if there’s anything else they’d like to discuss. Create space for them to share concerns, questions, suggestions, or personal experiences.
Wrap up with appreciation
Thank them for their time and—if necessary—share your next steps and 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, appreciate them for their contributions.
Sample Skip-Level Meeting Questions For Managers
| 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? |
| Information/feedback gathering on manager | What’s the best part of working with your manager? What’s the hardest part? What do you wish your 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 upholding 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 don’t love? If you were in charge, what’s one thing you would do differently? 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 see in my position? |
Tips for Implementing Skip-Level Meetings
Meet with everyone
This is a prix fixe menu, not an a la carte—it’s not fair to meet with only some skip-level team members. If you 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 manage 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).
Aim for meeting twice a year with each person
If you only have a handful of people to meet with, consider doing skip-levels quarterly.
Schedule 15 minutes after each meeting
Take time to synthesize the conversation, capture trends, and decide on next steps.
Common Mistakes to Avoid in Skip-Level Meetings
To ensure skip-level meetings are productive and build trust, avoid these common pitfalls:
- Undermining their manager’s authority by overruling their decisions or undercutting their management
- Not communicating your intentions to both managers and staff. Skip-levels shouldn’t be a secret.
- Skipping preparation so that the meeting feels aimless
- Overloading the agenda and trying to cover too much
- Not doing enough rapport-building so the meeting feels like an interrogation
- Failing to follow up if you’ve made a commitment or identified a next step
Post-Meeting Follow-Up Strategies
Strong follow-up helps staff feel like their time, energy, and feedback was valued and considered.
- Send a simple thank you message: “I really appreciated…”
- Repeat back key insights and next steps: Share your key takeaways and any action items that came from your meeting.
- Communicate with managers: Respect confidentiality, but also communicate general insights with managers to support their growth.
Ready to get started? Check our Skip-Level Meeting Sample Emails for informing managers and staff. Or, dive deeper with our Investing in People and Performance training (just make sure you’ve taken its equally helpful prerequisite).
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