Why Skip-Level Meetings Matter More Than Leaders Realize

One of the biggest leadership mistakes I see is leaders assuming they have a clear picture of what employees are experiencing simply because information is flowing through the org chart.

But the reality is… information gets filtered.

Managers soften things, employees stay quiet, concerns go unspoken, and frustrations build slowly over time.

Sometimes leaders don’t realize there’s a disconnect until engagement drops, turnover increases, or communication issues start creating larger problems.

That’s one of the reasons I’m such a big believer in skip-level meetings.

A skip-level meeting is a conversation between a leader and employees who report to one of their direct reports rather than directly to them.

When they’re done well, they create space for leaders to hear directly from employees who don’t report to them. And often, those conversations uncover insights leaders would not have gotten otherwise.

Not because people were intentionally hiding things, but because organizational communication is layered and imperfect by nature.

The quality of the conversation depends on the quality of the questions

A lot of skip-level meetings stay surface-level because the questions stay surface-level.

“How’s everything going?”

“Anything you need?”

“How’s the team doing?”

Those questions aren’t bad, but they rarely uncover the deeper insights leaders actually need.

The most effective skip-level conversations help leaders better understand:

• where communication is breaking down,
• what frustrations employees are navigating,
• where silos may be forming,
• and how leadership behaviors are impacting the employee experience.

Questions like:

• “What’s one thing leadership may not fully understand about your day-to-day work?”
• “What’s one recurring frustration that makes your job harder than it needs to be?”
• “Where do you see communication breaking down most often?”
• “What’s one thing your manager does that really helps you succeed?”

Those kinds of questions tend to create much richer conversations because they invite reflection instead of quick, guarded responses.

The best leaders stay curious

One of the things I appreciate most about strong leaders is their willingness to stay curious.

They don’t assume they automatically have the clearest perspective simply because they sit higher in the organization. They recognize there are always blind spots, and they intentionally create opportunities to listen.

That’s what skip-level meetings can do.

They help leaders identify patterns, strengthen trust, uncover frustrations early, and better understand the real employee experience before small issues become larger ones.

And honestly, sometimes one skip-level conversation reveals more than a dozen reports ever could.

A practical resource for your next skip-level meeting

One of the questions I get asked most often is:

“What should I actually ask during a skip-level meeting?”

So I put together a free resource with 20 practical questions leaders can use to create more meaningful skip-level conversations.

The questions are designed to help uncover insights around:

• employee engagement
• communication
• leadership support
• team dynamics
• growth opportunities
• retention risks

You can download it here: https://www.leannelagasse.com/skip-level-meetings

Remember, the goal isn’t just to hold more meetings - it's to understand your people more clearly so you can lead them more effectively.