What to Talk About in Skip Level Meetings: A Strategic Guide for High-Performing Teams

I. Introduction

In growing organizations—especially those with 40 to 70 employees—communication can make or break your momentum. As companies scale, leadership layers increase. That’s when skip level meetings become a powerful tool to keep everyone aligned and engaged.

A skip level meeting is a one-on-one conversation between an employee and their manager’s manager. It’s not about stepping over anyone’s authority. It’s about opening new lines of communication and gaining real, unfiltered insights from team members who are closest to the work.

If you’re a director, VP, or C-suite leader, these meetings can help you understand what’s really happening on the ground. They give you a chance to listen, support, and align teams with the company’s bigger goals.

Ready to make your skip level meetings more impactful? Let’s walk through exactly what to talk about—and how to structure these conversations for maximum value.

If you’re looking to streamline your meetings with ready-to-use templates, check out our free meeting templates here.

II. Establishing Rapport and Trust

Before diving into metrics or strategies, start with trust. Without it, employees may hold back. You’ll miss the valuable insights these meetings are designed to surface.

Why Trust Matters

For many employees, meeting with a senior leader can be nerve-wracking. They might worry about saying the wrong thing or being perceived as a complainer. That’s why it’s crucial to create a relaxed, open environment right from the start.

Start by saying something like, “This isn’t a performance review. I’m here to listen and learn from you.” That simple statement can lower defenses and open the door to honest conversation.

Easy Icebreakers to Get Comfortable

The first few minutes should feel casual. Ask questions that help the employee feel seen as a person, not just a worker.

• “How did you get into your current role?”
• “What’s something you’ve enjoyed working on recently?”
• “What’s a small win you or your team had this month?”

These questions help humanize the conversation and build rapport.

Lead by Example

Want your team to open up? Share a bit about yourself. Talk about a challenge you’ve faced or a lesson you’ve learned. When leaders show vulnerability, employees are more likely to do the same.

Also, be mindful of your tone and body language. Whether you’re meeting virtually or in person, keep it warm, focused, and informal. By investing a few minutes in building trust, you’re setting the stage for a much more productive and meaningful conversation.

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III. Discussing Team Achievements and Challenges

Once you’ve built rapport, move into the core of the conversation—what’s going well, and what’s not.

Celebrate the Wins

Start with the positives. Ask questions like:

• “What’s something your team has done really well lately?”
• “Who on your team has gone above and beyond?”
• “What’s one thing you’re proud of?”

Recognizing achievements boosts morale. It also helps you identify successful practices that could be shared across other teams.

Identify the Pain Points

Next, dig into the challenges. Ask open-ended questions to get honest feedback:

• “What’s the biggest obstacle your team is facing right now?”
• “Are there tools or processes that are slowing you down?”
• “Where do you feel friction in your day-to-day work?”

These questions help uncover issues that might not be visible at the top. It’s also a chance to spot problems before they escalate.

Ask How You Can Help

Here’s where skip level meetings become truly valuable. Ask:

• “What support do you need from leadership?”
• “Is there a decision you’re waiting on that’s slowing you down?”
• “What’s one thing leadership could do to make your job easier?”

These questions flip the script. Instead of managing from the top down, you’re empowering employees to shape how the company operates.

For more on how to structure these conversations, check out Harvard Business Review’s guide on skip level meetings.

IV. Aligning on Company Goals and Vision

Once you’ve covered achievements and challenges, it’s time to zoom out. Use this part of the meeting to connect individual work to the company’s larger mission.

Share the Big Picture

Start by briefly outlining the company’s current goals. For example:

• “One of our top focuses this quarter is improving customer satisfaction.”
• “We’re looking to expand into new markets over the next six months.”

This gives employees context. When people understand where the company is going, they can better align their work to support it.

Ask for Their Perspective

Next, ask how they see their team contributing to those goals. Try:

• “How does your team’s work support our strategic priorities?”
• “Are there areas where you feel disconnected from our goals?”
• “What could we do to improve alignment?”

This is where you might uncover gaps or misunderstandings that could be hurting performance.

Co-Create Solutions

Once alignment gaps are identified, ask for ideas. Employees often have smart, practical suggestions for improving processes or communication. Ask:

• “If you could change one thing to help us work more effectively, what would it be?”
• “What’s a small tweak that could make a big difference?”

Capture these insights and follow up. When employees see their ideas lead to action, engagement skyrockets.

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V. Providing and Receiving Feedback

Feedback is where growth happens. Skip level meetings are a great chance to give and receive feedback in a safe, constructive environment.

Give Thoughtful Feedback

If you’re offering feedback, make it specific and actionable. Use simple frameworks like:

• SBI (Situation – Behavior – Impact)
• Start-Stop-Continue (What to start doing, stop doing, and continue doing)

Example: “In last month’s sprint (Situation), your team adapted quickly when the requirements changed (Behavior), which helped us hit our deadline (Impact). That flexibility was impressive.”

Frame feedback as an opportunity, not a criticism.

Ask for Feedback in Return

Encourage employees to share their thoughts on leadership, culture, or team dynamics. Ask:

• “How do you feel about communication within your team?”
• “Is there anything leadership could be doing better?”
• “What’s one thing we could improve as a company?”

This feedback is gold. It helps you spot blind spots and improve the employee experience.

Make Feedback Actionable

The worst thing you can do is ask for feedback and then ignore it. Use tools like Meeting For Goals to document insights, assign follow-ups, and track progress.

For more on how to give and receive feedback effectively, check out this article from Gallup.

VI. Addressing Career Development and Growth

One of the most valuable parts of a skip level meeting? Talking about the employee’s growth.

Ask About Career Goals

Many employees don’t get the chance to discuss their long-term goals with senior leaders. Use this opportunity to ask:

• “Where do you see yourself growing within the company?”
• “Are there skills you’d like to develop?”
• “What kind of projects would you love to work on?”

These questions show that leadership is invested in their future.

Identify Growth Opportunities

Once you understand their goals, help them identify opportunities. Maybe it’s mentoring, cross-functional projects, or leadership training.

• “Are there stretch projects you’d be interested in?”
• “Would you benefit from more feedback or coaching?”
• “Is there a resource or course that could help you grow?”

This part of the conversation builds loyalty and retention. Employees are more likely to stay when they see a path forward.

Follow Up

Make sure to follow through on any development opportunities discussed. Whether it’s a training session or a new project, help them take the next step.

Use Meeting For Goals to assign action items and track progress over time.

VII. Wrapping Up and Following Through

As the meeting wraps up, summarize the key points. Reiterate what you heard, what actions you’ll take, and what they can expect next.

• “Thanks for sharing your thoughts today. I heard that your team is facing some process bottlenecks, and I’ll follow up with the operations team.”
• “You mentioned wanting to grow into a leadership role—let’s explore what stretch opportunities might be available.”

Set a reminder to check in again in a few weeks. Consistency builds trust.

And most importantly—take action. When employees see that their feedback led to real change, they’ll be more likely to engage in future conversations.

VIII. Conclusion

Skip level meetings aren’t just another calendar event. They’re a powerful way to connect strategy with execution, and leadership with the frontlines.

Let’s recap what makes a great skip level meeting:

• Start by building trust and rapport
• Celebrate wins and uncover challenges
• Align team efforts with company goals
• Exchange meaningful feedback
• Support career development
• Follow through on action items

When done right, these meetings can boost morale, spark innovation, and drive real performance improvements.

Looking to make your skip level meetings even more effective? Sign up for Meeting For Goals at https://app.meetingforgoals.com/TenantRegistration/Register. Our platform helps you create structured agendas, track goals, assign follow-ups, and ensure every meeting drives results.

Want to explore more ways to improve your meetings? Browse our free meeting templates at https://meetingforgoals.com/meeting_templates.

Every meeting is a chance to move your team forward. Let’s make them count.

Visit https://meetingforgoals.com to learn how we’re helping companies like yours turn meetings into a competitive advantage.