Skip-level meeting questions
A skip-level meeting is a conversation between a leader and the people who report to their direct reports. Done well, it surfaces what the leader can't see from above, without going around the manager in the middle. Here are questions for both sides and how to run it.
Lauren is a real coach. You're texting an AI trained on her coaching.
How to run one well
Tell the manager in the middle first
Explain why you're doing skip-levels and that you aren't checking up on them. Share themes with them afterward, not who said what.
Set expectations at the start
"This isn't a performance conversation, and I'm not here to overrule your manager. I want to understand what it's like on the ground."
Listen far more than you talk
Your job is to learn. Ask, wait, and ask a follow-up before you explain or defend anything.
Don't make promises in the room
If someone raises a problem, thank them and say what you'll do next. Fixing it without the manager undermines them.
Close the loop
Within a few weeks, share what you heard as themes and what changed because of it. If nothing ever changes, people stop telling you things.
Questions to ask, as the leader
- What's going well on your team right now?
- What's one thing that makes your work harder than it needs to be?
- Do you have what you need to do your best work?
- Is there anything leadership is doing that doesn't make sense from where you sit?
- Do you feel clear on how your work connects to the company's goals?
- What's something we should start, stop or keep doing?
- How are decisions communicated to you? Is anything getting lost?
- What skills do you want to build, and do you see a path to build them here?
- Is there anyone on your team doing great work that I should know about?
- If you were in my seat, what's the first thing you'd change?
Questions to ask your boss's boss
If you're the employee, come with two or three of these. It's a rare chance to understand the bigger picture and be seen.
- What are you most focused on this year?
- What does success look like for our department in the next six months?
- What's the biggest risk you see for our team?
- Where do you see our part of the business heading?
- What do people who grow fast here tend to have in common?
- Is there anything you wish teams like mine understood about leadership's decisions?
- Is there a project coming up that I could contribute to?
- What's one piece of advice you'd give someone at my stage?
Mistakes to skip
- Using it to evaluate the manager. Questions like "How's your manager doing?" put people in an impossible spot. Ask about the work.
- Fixing problems behind the manager's back. Bring themes to the manager and solve them together.
- Treating it as a complaint session, if you're the employee. Bring curiosity and one or two constructive observations.
- Holding just one. Trust builds over several conversations, not one.
Prep with Lauren
got a skip-level with our VP thursday. what do I even talk about. don't want to throw my boss under the bus
good instinct. a skip-level is a chance to be seen thinking about the business, not to vent
bring two questions about the big picture and one thing you're working on that you're proud of
like what
"What does success look like for our org in six months?" and "Is there a project coming up I could help with?" then 30 seconds on the onboarding fix you did. curious, useful, visible
Make the rare meeting count.
Text Lauren who you're meeting and what you want them to know. She'll help you pick the questions and the one story to tell.
Hi Lauren! I have a skip-level meeting coming up and want help preparing.
Lauren is a real coach. You're texting an AI trained on her coaching. Your first week is free. Cancel anytime from your account or by texting Lauren.
Frequently asked questions
What is a skip-level meeting?
A meeting between a leader and someone who reports to one of their direct reports. It helps leaders hear what's happening on the ground and helps employees understand the bigger picture.
How often should skip-level meetings happen?
Monthly or quarterly is common. Consistency matters more than frequency, because trust builds over several conversations.
What should I not say in a skip-level meeting?
Avoid personal complaints about your manager unless it's serious; HR is the better route for that. Focus on the work, the obstacles you see, and your own growth.