Prompt
Skip-Level Meeting Prep
Use this when you need questions and topics prepared for a skip-level meeting with your manager's reports.
How to use it
- Copy the prompt and paste it into ChatGPT, Claude, Gemini or any other AI.
- Replace every {{placeholder}} with your own details, or let the AI ask you for them.
- Use the follow-ups below to go deeper.
Role — You are a people manager preparing for a skip-level meeting with your manager's direct reports, focused on genuine listening rather than status reporting.
Context you provide
- {{meeting_context}} — who the skip-level is with, which team or reports, and how often these happen
- {{known_topics}} — anything already known that's relevant, such as recent changes, known concerns, or team dynamics
- {{your_goals}} — what you want to learn or accomplish, such as a pulse-check on morale, surfacing blockers, or hearing about a specific manager's leadership
- {{sensitivities}} — anything to navigate carefully, such as not wanting to undermine the direct manager or sensitive recent events
Instructions
- Ask for any missing inputs before preparing.
- Draft six to ten open-ended questions grouped by theme — team health, growth and development, process and blockers, feedback on leadership — tied to your stated goals.
- Avoid yes/no questions; favor ones that invite specifics, such as "what's slowing you down" rather than "is everything okay."
- Add guidance on handling sensitivities, such as how to ask about their manager without inviting a complaint session that undermines trust.
- Suggest a closing question that invites anything not yet covered.
Output format — A prep sheet with grouped questions by theme and a short "how to handle sensitive topics" note. Conversational, a loose guide to bring into the meeting, not a script to read verbatim.
Guardrails — Do not invent team issues or history that weren't provided. Keep questions neutral and non-leading, especially around the direct manager's performance, to avoid putting words in anyone's mouth.
Example — meeting_context: "quarterly skip-level with 6 reports on a manager's team"; known_topics: "team recently went through a reorg"; your_goals: "check morale post-reorg, hear if the new manager is settling in well"; sensitivities: "don't want reports to feel like this is an evaluation of their manager."