Understanding Employee Experience Through Skip Level Conversations

Here’s the thing about leadership—what you think is happening in your organization and what’s actually happening are often two very different things. 

That’s where skip-level meetings can come in. 🚶🏻‍♂️

When they're used well, they’re one of the most powerful tools for uncovering the real challenges employees face, spotting culture shifts before they become retention issues, and—most importantly—building trust.

But let’s be honest: A lot of leaders aren’t using them to their full potential.

Some treat them like check-the-box exercises. Others turn them into interrogations. And some avoid them entirely because, well… what if they hear something they don’t like?

If you’re a leader who wants skip-levels to actually make an impact, here’s what you can do.

Stop Treating Skip-Levels Like Just Another Meeting

Skip-levels are not status updates. They’re not casual “How’s it going?” conversations. And they’re not a chance to evaluate employees (spoiler alert: that’s how you get rehearsed, overly cautious answers).

Instead, they should feel like an opportunity for employees to speak freely, without layers of hierarchy shaping the message.

Done well, skip-levels help leaders:

✅ Spot roadblocks before they turn into resignations

✅ Understand what’s really frustrating employees (not just what managers say)

✅ Identify high-potential talent that might be overlooked

✅ Strengthen trust across the organization

Sounds great, right? Except most leaders don’t realize that your employees may not trust you yet.

If skip-level meetings feel like a pop quiz, employees will default to safe, surface-level answers.

That’s why it's so important that psychological safety is the highest priority. If people believe there will be consequences for their honesty (or that their feedback will go straight back to their boss), you won't get the honest feedback you're looking for.

To build trust in skip-levels:

👂 Be clear about your purpose. “I want to understand what’s working and what’s not—so we can make better decisions.”

🔄 Don’t use feedback against people. These meetings are about learning, not performance management.

📢 Share what you’re hearing. If employees don’t see action (or at least transparency about why change is hard), they won’t bother opening up next time.

And while we’re on the subject…

If You’re Not Asking the Right Questions, You're Missing the Point

Skip-level meetings shouldn’t feel like small talk. The right questions spark real insights. Instead of generic “How’s it going?” try questions like:

👉 “What’s something about your job leadership probably doesn’t see?”

👉 “Where do you see silos forming, and how does that impact your work?”

👉 “If you decided to leave, what do you think the main reason would be?”

The goal isn’t just to gather feedback—it’s to understand how employees actually experience your organization. Because when employees feel like they're not being heard is when they start to disengage.

The Bottom Line

Skip-level meetings aren’t about simply checking in.

The most intentional leaders use them to uncover blind spots, fix what’s broken, and to show employees that leadership isn’t as disconnected as it sometimes seems.

So ask yourself this: Are your skip-levels actually making an impact? Or just taking up space on your schedule? 🧐

Let’s make them count.

 👉🏻 Here’s a free resource to help you lead more meaningful skip-level conversations with your team.

Click here to download "Twenty Powerful Questions to Ask in a Skip-Level Meeting."

This tool will help you gather real insights, strengthen trust, and show your team that leadership is truly listening. ✨

Hey, thanks for being here and for watching/reading. My goal is to consistently create content that's engaging, applicable, and inspires you to continue learning and growing as a leader. If you have ideas for future content or any questions at all, please shoot me an email at: [email protected].