The Skip-Level Anxiety
Your manager's manager wants to meet with you. The immediate thought: 'Am I in trouble?' The second thought: 'Should I bring up the thing that's been bothering me about my manager?' The third thought: 'How do I look impressive without looking like I'm trying too hard?'
Skip-level meetings aren't investigations. They're how senior leaders stay connected to what's actually happening on the ground. Your skip-level manager wants to hear about your work, your perspective on the team, and whether anything's broken that they can't see from their altitude.
The key tension: being honest and useful without creating political problems with your direct manager. These templates navigate that.
The Pre-Meeting Prep Email to Your Manager
Always give your direct manager a heads up before a skip-level. Not asking permission — informing them.
Hi [Manager], [Skip-level manager] scheduled a 1:1 with me for [date]. Wanted to let you know. I'm planning to share updates on [projects] and discuss [neutral topic like career development or team process]. Anything specific you'd like me to raise or keep them informed about? [Your name]
This email does three things: it shows respect for your manager, it gives them a chance to align on messaging, and it prevents the worst-case scenario where your manager hears about the meeting from someone else and assumes you went over their head.
What to Say in the Meeting
Lead with your work: 'I've been focused on [project]. Here's where we are and what I'm learning.' This grounds the conversation in substance, not politics.
When asked about team dynamics: 'The team is strongest at [genuine strength]. One area where I think we could improve is [process or structural issue, not a person].' Notice the frame — you're talking about processes, not people. 'Our deployment process could be smoother' is constructive. 'My manager doesn't prioritize deployment' is political.
When asked what you need: be specific. 'More resources' is vague. 'If we had one more engineer on the API team for Q3, we could hit the integration deadline without burning out the current team' is actionable.
What Never to Say in a Skip-Level
Never complain about your direct manager by name. Even if the skip-level manager asks directly. Frame issues as structural, not personal. 'I think the team could benefit from clearer prioritization frameworks' is the same feedback as 'My manager can't prioritize,' but one builds your reputation and the other destroys it.
Never use a skip-level to lobby for a promotion or raise. That conversation belongs with your direct manager. Going over their head signals that you don't trust the normal process — and the skip-level manager will note that.
Never say 'everything is fine' when it isn't. Skip-levels exist because senior leaders know that 'everything is fine' is rarely true. Sharing one genuine challenge — framed constructively — shows maturity and gives them useful information.
After the Meeting
Send a brief thank-you to the skip-level: 'Thanks for taking the time today. I appreciated the conversation about [specific topic]. Looking forward to [specific thing discussed].'
Update your direct manager: 'Had a good conversation with [skip-level]. We discussed [topics]. They seemed interested in [specific point]. Nothing unexpected.' This closes the loop and prevents your manager from wondering what was said.
The goal of every skip-level: leave the senior leader thinking 'that person is thoughtful, competent, and a good addition to the team.' Not 'that person is political' or 'that person has an agenda.' Substance over strategy. Always.
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