What to Discuss in a Skip Level Meeting: A Guide for High-Performing Teams

Excerpt:

Skip level meetings are one of the most underutilized yet powerful tools that high-performing organizations can use to foster transparency, boost morale, and align teams with strategic goals. But what makes these meetings truly impactful? In this guide, we dive into the key topics and strategies that make skip level meetings effective, actionable, and aligned with your company’s mission. Whether you’re a VP, Director, or C-suite executive at a mid-sized company, this article will show you how to unlock the full potential of skip level meetings using the Meeting For Goals platform.

Start transforming your leadership approach today. Sign up for Meeting For Goals at https://app.meetingforgoals.com/TenantRegistration/Register and explore our free meeting templates to get started: https://meetingforgoals.com/meeting_templates.

Introduction

What Is a Skip Level Meeting?

A skip level meeting is a conversation between a senior leader and an employee who doesn’t report directly to them. It skips one level of hierarchy, allowing executives to connect with team members they don’t normally engage with.

These meetings are more than just a check-in—they’re a strategic opportunity to gather honest feedback, understand team dynamics, and reinforce company values.

Why They Matter for High-Performing Teams

High-performing teams thrive on transparency, trust, and alignment. Skip level meetings support all three. They give leaders a clearer view of what’s happening on the ground and help employees feel seen and heard by upper management.

At Meeting For Goals, we believe meetings should be purposeful and aligned with your business goals. Our platform helps you plan, run, and follow up on skip level meetings efficiently, so you can drive real results.

Section 1: Setting the Agenda

Start With a Clear Purpose

Every great meeting starts with a purpose. Without it, conversations can become vague or unproductive. Before the meeting, ask yourself:

• What do I want to learn?
• What issues do I want to uncover?
• What value should both sides walk away with?

Clearly defining the meeting’s goal ensures that you make the most of your time. Whether it’s understanding morale, surfacing challenges, or aligning on goals—clarity is key.

Suggested Agenda Topics

To keep things focused, here are a few agenda items that work well:

• Current project updates and challenges
• Team morale and engagement
• Feedback on leadership and communication
• Alignment with company goals
• Career development and growth opportunities

With Meeting For Goals, you can create and share your agenda ahead of time. This helps employees come prepared and encourages meaningful discussion.

Collaborate on the Agenda

Don’t build the agenda alone. Involve your employee in the process. Ask them to submit questions or topics they’d like to discuss. This makes the meeting more balanced and shows that you value their input.

Use a shared document or a quick pre-meeting survey to collect their thoughts. On your side, bring data or insights that will help guide the conversation.

Our platform makes this easy with built-in agenda collaboration tools. You can even link agenda items to company goals, ensuring strategic alignment throughout the conversation.

Section 2: Discussing Team Performance and Challenges

Talk About Projects—From the Ground Up

Skip level meetings are a great way to hear how projects are going—straight from the people doing the work. While reports and dashboards are helpful, nothing beats a real conversation.

Ask questions like:

• What’s going well in your current projects?
• Are there any recent wins you’re proud of?
• What would make your work easier?

These questions show genuine interest and help you spot patterns or successes that might otherwise go unnoticed.

Meeting For Goals allows you to tie these discussions back to strategic objectives so you can track progress and celebrate wins company-wide.

Uncover Hidden Roadblocks

Beyond successes, you also want to learn about the challenges teams are facing. Sometimes employees are hesitant to raise issues with their direct manager. A skip level meeting can feel like a safer space.

Try asking:

• What’s been the biggest challenge recently?
• Is anything slowing you or your team down?
• How can leadership better support you?

These questions open the door to honest feedback. When you listen with empathy and curiosity, you’ll uncover insights that can help you make better decisions.

Document these discussions in Meeting For Goals. Assign follow-up tasks and ensure the right people are accountable for resolving issues.

Section 3: Sharing Feedback and Insights

Make It a Two-Way Street

Skip level meetings shouldn’t feel like an interview. They should feel like a conversation. This is your chance to listen, learn, and connect.

Encourage employees to share their thoughts openly. Ask:

• What’s something you wish leadership understood better?
• What’s one thing we could improve as a company?
• How do you feel about our direction?

These types of questions help uncover valuable insights that might not surface in regular team meetings.

Capture these insights in Meeting For Goals and categorize them by theme—whether it’s operations, culture, or innovation. This helps you spot trends and take action.

Give Constructive Feedback

While the focus is on listening, don’t miss the chance to give feedback too. This isn’t about critiquing performance—that’s for their direct manager. Instead, offer encouragement, guidance, or recognition.

If someone shares a creative idea, acknowledge it. If you see a leadership trait in them, point it out. These moments build confidence and reinforce the behaviors you want to see more of.

You can also use this time to gently realign any misunderstandings about company values or priorities.

With Meeting For Goals, you can document feedback, assign action items, and track follow-ups. This turns feedback into growth.

Section 4: Aligning on Company Goals and Vision

Bridge the Gap Between Strategy and Execution

In many companies, there’s a gap between what leadership plans and what employees experience. Skip level meetings help bridge that gap.

Use this time to talk about the company’s goals—and how each employee’s work contributes to them.

Ask:

• Do you understand how your work supports our mission?
• Are there any goals that feel unclear or disconnected?
• What would help you feel more aligned?

These conversations ensure that everyone is rowing in the same direction.

Meeting For Goals lets you link each meeting topic to a strategic objective, creating a clear line from vision to execution.

Reinforce Company Values

Your company’s values should be more than just buzzwords. They should guide behavior, decisions, and culture.

Use skip level meetings to bring these values to life. Share examples of how teams are living them out. Ask employees:

• When have you felt most aligned with our values?
• What do our values mean to you?
• Are there areas where we’re falling short?

These conversations deepen engagement and create a shared sense of purpose.

You can track these insights in Meeting For Goals and use them to inform future culture initiatives.

For more tips on aligning your team with your company’s mission, check out this helpful article from Harvard Business Review: https://hbr.org/2021/12/what-is-your-companys-purpose

Section 5: Opportunities for Professional Development

Understand Career Goals

Employees want to grow. But often, their aspirations aren’t fully known to leadership. Skip level meetings are a great time to learn more.

Ask:

• What skills are you excited to develop?
• Are there any roles or projects you’d like to explore?
• Do you feel supported in your growth?

These questions show that you care about their future—and help you identify opportunities for mentorship, training, or stretch assignments.

Meeting For Goals helps you document these conversations and assign relevant follow-ups, like enrolling in a course or connecting with a mentor.

Encourage Learning and Upskilling

High-performing teams never stop learning. Use skip level meetings to promote a culture of continuous development.

You might:

• Share upcoming training or learning resources
• Recommend a book, podcast, or course
• Encourage participation in cross-functional projects

If you hear the same development needs across multiple employees, consider launching a team-wide initiative—like a workshop or guest speaker series.

Check out this guide from McKinsey on building a learning culture: https://www.mckinsey.com/capabilities/people-and-organizational-performance/our-insights/creating-a-learning-culture

With Meeting For Goals, you can track these initiatives and measure their impact on performance and engagement.

Conclusion

Skip level meetings are more than just a leadership tactic—they’re a powerful tool for transparency, alignment, and growth.

To recap, here’s what makes a skip level meeting effective:

• A clear, shared agenda
• Honest conversations about performance and challenges
• Two-way feedback and insights
• Alignment on goals and values
• A focus on learning and development

When done right, skip level meetings strengthen your culture, improve morale, and help you lead with intention.

Ready to make skip level meetings part of your leadership toolkit? Start now with Meeting For Goals. Sign up here: https://app.meetingforgoals.com/TenantRegistration/Register

Want to save time planning your next meeting? Explore our free meeting templates: https://meetingforgoals.com/meeting_templates

For more tips, strategies, and tools to power high-performing teams, visit https://meetingforgoals.com

Final Thoughts

In a fast-moving business world, staying connected with your team is more important than ever. Skip level meetings offer a rare chance to listen deeply, align strategically, and lead with empathy.

With the right approach—and the right tools—you can turn these meetings into a competitive advantage.

Start your journey toward better leadership today. Your team will thank you.