Skip-Level Meetings: How to Get Honest Answers From Your Team

What is a skip-level meeting?

A skip-level meeting is when a leader sits down directly with employees who are two or more rungs below them on the org chart, without their manager in the room.

These honest, unfiltered conversations matter because the farther you sit from the front line, the more your picture of the business gets smoothed out on the way up to you. People just naturally round the edges off bad news before it reaches your desk, because nobody wants to be the one who brings you a problem. A skip-level meeting is one of the few tools that lets you hear the honest perspective, without any rounding

It's simple in concept but may feel a little awkward in practice. A CEO, Executive, or Upper-Level Manager sits down with individual contributors or direct reports to get an unfiltered read on how the business is running, straight from the people doing the work. The point isn't to go around anyone or build a case against a manager, it’s to improve organizational communications and employee engagement.

Is a Skip-Level Meeting Worth the Awkwardness?

At Rhythm Systems, we push teams to build a culture where status updates are honest: a goal gets marked red when it's actually red, not yellow because red feels uncomfortable to report. Skip-level meetings apply that same principle to people instead of metrics. When done well, they will give you a second data source on what's really happening, one that skips the layers of people deciding what you do and don't need to hear.

These conversations will do something a quarterly engagement survey never will. They let an employee feel heard by someone who can change things, in a real conversation, in real time. And you’ll get a better sense of the work environment and the challenges facing the people closest to the work.

How should I Run a Skip-Level Meeting So People Actually Trust Me?

Tell the manager first, every time. A skip-level meeting that feels like it happened behind someone's back will make that manager defensive and make everyone else assume you're building a case against them. It also helps on the other side: when an employee knows this isn't an investigation into their manager, they feel safer being honest with you instead of giving you the polished version.

Say the quiet part out loud. Open by telling people plainly that this isn't a performance review, that they weren't picked because something's wrong, and that the conversation stays between the two of you. Most of the anxiety in the room comes from people not knowing why they were called in, and it dissipates quickly if you're upfront from the start.

Protect what gets shared. If you tell an employee the conversation is private, yet something they tell you finds its way back to them through their manager…you won't get an honest answer from anyone again. You know this, but word travels and your people talk to each other. If you need to act on something, find a path that doesn't point straight at your source.

Give people a heads-up. A short agenda sent in advance, covering roughly what you'll talk about, how long it'll take, and that it's informal, turns 'the CEO wants to see me' from a moment of panic into a normal meeting. Vague notice like 'can we chat Thursday?' causes almost as much anxiety as no notice at all, and when people aren't caught off guard, you get thought-out answers instead of the first safe thing that comes to mind.

Act on what you hear. You don't have to fix everything, but closing the loop, telling someone what happened with what they brought up (even if the answer is no or not yet) shows you took it seriously. Silence often reads the same as inaction, so if a few of these meetings pass with no visible follow-through, people will decide these are just for show and that opinion spreads fast.

Skip-Level Meeting Questions, Organized by What You're Trying to Learn

In advance of your meeting, pick two or three from whichever category matches what you're trying to find out, and let the conversation go where it goes from there.

Team Health and Trust

• What's one thing your manager does that makes your job easier?

• If you could change one thing about how this team works together, what would it be?

• Do you feel like you can flag a problem without it coming back on you later?

• What do you wish leadership understood about what your day actually looks like?

• Where's the team right now: energized, fine, or just getting through the week?

Strategy and Alignment

• In your own words, what is the company trying to accomplish this year?

• Where do you see a gap between what leadership says and what happens day to day?

• What's slowing your team down that people at my level probably don't see?

• If you were setting next quarter's priorities, what would make the list?

Growth and Development

• What skill do you want to build that you're not getting the chance to right now?

• Where do you want to be in two years, and what's standing in the way?

• If you're honest, what would make you consider leaving?

• Who on this team deserves more credit than they're getting?

Culture and Process

• What's the one process everyone complains about that nobody's fixed?

• If you ran this department for a week, what's the first thing you'd change?

• What meeting, tool, or habit is costing more time than it's worth?

• What's one small change that would make a bigger difference than people realize?