A skip level meeting template that gets past the polite version

My first skip levels were useless for about a year. I would book thirty minutes with someone's report, ask how things were going, hear that things were going well, and leave with nothing I did not already know. Both of us were performing. The person was being careful in front of their boss's boss, and I was asking questions that made being careful the rational choice.

What fixed it was not better questions, though questions matter. It was structure. A skip level has an unusual shape compared to a normal 1-1, and once I started treating it as its own format with its own template, the answers changed. This is that template, with the reasoning for each part, because a template you understand beats a template you copy.

If you want the questions themselves, there is a fuller set in skip level meeting questions that are worth the awkwardness. This article is about the container the questions go in.

Before the meeting: the part everyone skips

A skip level starts three days before the meeting, with a short message. People walk into skip levels braced. They do not know what you are fishing for, and the safest strategy for them is to say nothing memorable. A message before the meeting takes the ambush out of it.

What I send, roughly verbatim:

Booking our quarterly skip level for Thursday. No agenda from my side beyond wanting to hear how the last few months have felt from where you sit. Useful things to think about beforehand: what the team is doing well, what is harder than it should be, and anything you wish my level understood better. Nothing you say gets repeated to your manager with your name on it.

The last sentence is the load-bearing one. Say it in writing, not just out loud. And only say it if it is true. If you plan to relay specifics back to their manager, say that instead, or do not hold skip levels at all.

The other prep is on my side. I read the person's recent work, check what I know about their manager's last few months, and look at my notes from our previous skip level if there was one. Walking in cold tells the person this meeting is a formality, and they will match that energy.

The template, six sections in order

Thirty minutes, six parts. The order matters. It goes from safe to less safe, because honest answers about leadership do not come out in minute two.

• Warm up, 3 minutes. How is life, what are you working on right now, is the workload sane. This is not filler. It sets the register as a conversation, not an interview.
• The work, 5 minutes. What has gone well lately, what is stuck, what is slower than it should be. You are listening for process problems you are too senior to see day to day.
• The team, 5 minutes. How is the team working together, who is carrying a lot, is there friction. Ask who has been helpful to them lately. The names that come up are your hidden leaders.
• Their manager, 7 minutes. The hardest section. I never ask how is your manager. I ask what does your manager do that helps you do your best work, and what is one thing you wish they did differently. Framing it around help, not judgment, is what gets a real answer.
• My level, 7 minutes. What is leadership doing that makes no sense from where you sit. What decision of the last quarter would you reverse. This is the part the meeting exists for, and the part most skip levels never reach.
• Close, 3 minutes. One thing you will take away, stated out loud. And the explicit repeat: what stays between us, and what I would want to pass on, agreed in the room.

A real example, filled in

Here is what a completed page looks like, from a skip level with a mid level engineer on a platform team. Names changed, content not.

• Work: proud of the caching rewrite, shipped early. Stuck: deploy approvals take two days and nobody can say why. Flag for me.
• Team: called out Lena twice as the person who unblocks everyone. Quiet tension with the QA handoff, nothing dramatic.
• Manager: weekly 1-1s happen and are good. Wishes manager pushed back on deadline changes instead of absorbing them silently. Pattern worth watching, not a crisis.
• My level: the reorg announcement made no sense to anyone below director. They heard about the team split from a rumor a week before the email. That one is on me.
• Agreed to pass on: deploy approval complaint, anonymized. Everything else stays here.

Three lines per section is enough. If I write more than that, I am transcribing instead of listening.

What to write down after

The notes are not the record of the meeting. They are the setup for the next one. I write the same three things every time, right after the call while it is fresh: what was said, what changed since last time, and what is open.

Open means anything I said I would look into. The deploy approval complaint above is open until I either fix it or explain why it stays. If a skip level produces no open items, it was probably too polite.

Then the loop has to close. Three months later, the single most valuable sentence in a skip level is last time you told me X, here is what happened with it. That sentence is why people tell you the truth the second time. I keep these notes in LeaderCues alongside the rest of my 1-1 notes, mostly because it surfaces the open threads before the next meeting without me having to remember they exist. A doc works too, as long as you actually re-read it.

Three mistakes that wreck the format

• Doing it once. A first skip level is always stiff. The honest one is the third or fourth, after the person has seen that nothing they said came back to hurt them. Quarterly is the minimum cadence that builds that.
• Quoting people to their manager. The fastest way to end skip levels on your whole team is one sentence like Anna told me she disagrees with the roadmap. Pass on themes, never quotes, and only what you agreed in the room.
• Replacing the manager's 1-1. A skip level is a sample of the layer below yours, not a parallel reporting line. If someone is using your skip level to route around their manager every month, that is a problem to name, not a channel to encourage.

The template above is the whole thing. A message before, six sections in order, three lines of notes after, and one open thread closed before the next round. None of it is clever. It works because the structure tells the person it is safe to be useful.