How to Run Skip-Level Meetings That Build Trust Across Your Org

2026-07-01 · 6 min read · 1:1 Meetings

Skip-level meetings — where you meet 1:1 with someone who reports to one of your direct reports — are one of the most underused tools in a manager's toolkit.

Done well, they give you a ground-level view of team health, surface problems your EMs might not be aware of (or might be the cause of), and build relationships that make your org more resilient. Done badly, they undermine your EMs and create confusion about who actually makes decisions.

Here's how to do them well.

Why Skip-Levels Matter

Your direct reports, even the excellent ones, have a filter. They summarise, they prioritise, they (consciously or not) shape the information that reaches you. This isn't dishonesty — it's human nature. We all present our worlds through our own perspective.

Skip-levels give you access to signal that doesn't go through that filter. Engineers will tell their skip-level manager things they won't tell their direct manager — especially about team culture, how processes feel, and how effective their manager is.

This is especially important when:

A team seems to have high attrition or low morale
You're hearing inconsistent signals about a team's health
You want to understand what's blocking engineers at the ground level
You're evaluating an EM's performance and need a fuller picture

The Risk: Undermining Your EMs

The biggest risk of skip-levels is that they signal distrust in your EMs — to the EMs themselves, and to the engineers who wonder why their boss's boss is suddenly interested in them.

Avoid this by being transparent:

Tell your EMs before you run skip-levels. Don't surprise them. "I like to meet with everyone on the team a couple of times a year to stay connected. I'll be meeting with your reports over the next few weeks."
Don't use skip-levels to make decisions that belong to the EM. If an engineer tells you about a problem in a skip-level, your first move is usually to bring it back to the EM — not to solve it yourself.
Don't share specifics of what individuals told you with the EM. "I'm hearing that deployment process is a source of friction" is fine. "Vikram told me he thinks the sprint planning is broken" is not.

The goal is better information, not to create a shadow management structure.

What to Ask

Skip-levels work best when they feel like genuine connection, not an audit. Start with relationship-building:

"Tell me a bit about what you're working on right now. What's the most interesting part of it?"
"What do you find most energising about your work here?"
"What's something you're trying to get better at?"

Then move to team and environment:

"What does the team do particularly well?"
"What's the one thing you'd change about how the team works if you could?"
"Is there anything you feel like isn't getting enough attention that you wish someone would notice?"
"Do you feel like you have what you need to do your best work?"

Finally, close with:

"Is there anything you wanted to share that I didn't ask about?"
"Is there anything you'd want me to know about what would make this a place you'd want to stay for a long time?"

This last question is particularly powerful. You'll hear things you wouldn't get any other way.

What to Do With What You Hear

After a round of skip-levels, you should synthesise themes — not individual comments. Look for patterns: Is the same complaint showing up across multiple people? Is there a particular team or individual consistently mentioned? Is the morale picture consistent or fragmented?

Take the themes back to the relevant EMs. Frame it as shared information, not a verdict: "I picked up a theme around deployment friction in a few conversations. Is that something you're aware of? What's your read on it?"

If something serious comes up — a concern about safety, discrimination, or serious management failure — you handle it directly and immediately, not via the EM.

Cadence

For most teams, skip-levels twice a year per person is a good cadence. Quarterly if you're concerned about a particular team's health. Monthly skip-levels start to feel like surveillance rather than connection.

If you're managing a large org (3+ EMs, 15+ engineers), you probably can't do skip-levels with everyone. Prioritise: newer employees (who haven't built trust yet), teams you're less confident about, and people who seem disengaged in broader forums.

One Thing That Makes Skip-Levels Better

Follow up. If someone mentioned a goal in your skip-level six months ago, ask how it's going when you next meet. If someone raised a concern and you addressed it, close the loop: "You mentioned the deployment process felt frustrating — we made some changes. Is it better?"

This is what turns a skip-level from an interrogation into a relationship. And it's the thing most managers skip.

People remember that you remembered. In a world where engineers often feel like cogs in a machine, being seen and followed up with is remarkably rare — and remarkably powerful.