How to Maximize a Skip Level Meeting

If we are being honest, a skip level meeting can feel… well… awkward.

You’re meeting with your boss’s boss, someone you probably don’t interact with daily, and now you’re expected to have a polished, insightful conversation.

What are you supposed to say?

Are you being evaluated?

Is this your chance to shine, or a subtle warning sign?

All those thoughts are normal.

But here’s the truth: skip level meetings are a gift.

They give you face time with a decision-maker. They offer a rare chance to give and receive feedback directly. And when handled well, they can help you grow, increase your visibility, and align your leadership with broader business goals.

Let’s break down exactly how to make the most of this opportunity, without overthinking it.

First, What Is a Skip Level Meeting?

It’s simple: a skip level meeting is when you meet with your manager’s manager.

You’re “skipping” a level in the org chart to create a direct communication bridge between frontline or mid-level employees and upper leadership.

That’s it.

There’s no secret agenda.

These meetings are meant to build connection, gather feedback, and make sure leaders understand what’s happening on the ground, beyond the filtered updates they typically receive.

They’re not about getting anyone in trouble. They’re about breaking silos and building trust.

Why They Matter

Skip level meetings are rare. And that’s exactly why they’re important.

When you’re managing a team or leading projects, most of your attention goes to execution, solving problems, coaching your team, delivering results. But how often do you get the chance to step back and connect with the people steering the bigger ship?

Your skip level manager holds influence over larger strategic decisions, and likely plays a role in succession planning, team structure, and leadership development.

This makes skip level meetings an opportunity to show alignment and maturity in your leadership style. If you’re early in your leadership role, this is especially important; check out what to prioritize in your first 90 days.

If you want to grow, be more visible, or just understand where your organization is headed, these meetings are gold.

Set the Right Tone

Let’s start with your mindset.

This is not a performance review. It’s not a pop quiz. It’s a conversation.

The best thing you can do is show up curious, open, and grounded in your desire to learn.

Here’s a simple way to set the tone:

“Thanks for taking the time to meet with me. I’m looking forward to hearing your perspective and getting your feedback. I’d love to understand how I’m doing from your point of view and how I can better support the bigger picture.”

Short. Professional. Respectful.

And it tells them right away, you’re here to grow.

What to Talk About: Smart Questions to Ask

You don’t need a long list of talking points. Just a few strong, thoughtful questions can open up a meaningful discussion.

Here are five categories you can lean into during your skip level meeting. Pick a few questions from each, and let the conversation flow naturally.

1. Leadership & Performance Feedback

You don’t often get feedback from leaders above your direct supervisor. Take advantage of it.

Ask questions like:

• “How do you view my leadership so far?”
• “Are there any areas where you think I can improve or stretch myself more?”
• “What stands out to you, good or bad, about how I lead my team or approach my role?”

These questions signal that you’re open, not defensive. That’s a powerful message.

2. Team & Culture Insights

You know your team from the inside. But your skip level manager might have a broader perspective.

This is a good time to ask:

• “From your point of view, how is my team doing?”
• “Are there any concerns or opportunities you see that I might not be aware of?”
• “Is there anything I should be focused on from a cultural or engagement standpoint?”

You’re not just asking how you are doing, you’re asking how your team is showing up. That’s leadership.

3. Strategic Alignment & Visibility

Upper leadership spends a lot of time on strategy. This is your chance to make sure you’re aligned.

Try questions like:

• “What are the top priorities at your level that I should be aware of?”
• “Are there any major initiatives that I should be helping drive or support more closely?”
• “Do you feel I’m visible and engaged at the right level, or are there areas where I could step up more?”

These show that you’re not just managing tasks, you’re thinking about impact.

4. Business Awareness

Most frontline and mid-level leaders stay in the tactical zone. You stand out when you show business acumen.

Ask things like:

• “What upcoming changes or challenges should I be preparing my team for?”
• “How do you see our department contributing to the organization’s bigger goals this year?”
• “Are there trends or risks I should be more aware of to lead more effectively?”

It shows you care about more than just your lane. You’re looking at the whole highway.

5. Growth & Career Development

A skip level meeting is a great opportunity to talk about your career, but do it thoughtfully.

Stay focused on development, not promotion.

Some strong questions:

• “What do you look for in leaders who move into bigger roles?”
• “What skills or experiences should I be building to grow within the organization?”
• “Do you see any opportunities I might not be taking advantage of?”

When you frame it like that, you sound intentional, not entitled.

Listen More Than You Talk

This might be the most important part.

Try something like:

“That’s really helpful, could you give me a specific example of what that looks like?”

You’ll get more actionable feedback, and they’ll see that you’re invested.

Avoid These Common Mistakes

Here’s what not to do in these skip level meetings:

• Don’t complain about your boss or coworkers. It puts your skip level manager in a tough spot and makes you look unprofessional.
• Don’t treat it like a job interview. You’re already in the room, just be real and open.
• Don’t act like you have it all figured out. Leaders appreciate humility and self-awareness far more than perfection.

Go in as a learner, not a performer.

End the Meeting with Clarity

Before the meeting wraps up, take a moment to summarize what you’re walking away with.

It might sound like:

“I appreciate the feedback on [insert area]. I’ll work on that and make sure I’m reinforcing [key initiative] with my team. If you think of anything else that would help me grow, I’d love to hear it.”

That last line is gold, it keeps the door open and shows you’re serious.

After the Meeting: Take Action

Now comes the real work.

Apply the feedback you obtained from this skip level meeting. Circle back with your direct manager if appropriate. And if you committed to anything in the meeting, follow through.

One of the best things you can do is send a short thank-you note. Doesn’t have to be formal. Just a few lines to say thanks and share a takeaway or two.

That one follow-up email can build a long-lasting impression.

Wrapping Up

Skip level meetings are one of those rare leadership moments that offer more than they ask.

They don’t require perfection.
They don’t demand a performance.
They just require presence.

When you show up curious, ask smart questions, and follow through, you’re doing more than having a meeting, you’re building trust.

And trust is the currency of leadership.

So whether this is your first skip level meeting or your tenth, approach it with purpose. Ask the questions that matter. Listen for what’s not being said. And walk out with a clearer sense of who you are, how you’re doing, and where you’re going.

That’s leadership in action.