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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

  1. Copy the prompt and paste it into ChatGPT, Claude, Gemini or any other AI.
  2. Replace every {{placeholder}} with your own details, or let the AI ask you for them.
  3. Use the follow-ups below to go deeper.
Prompt

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

  1. Ask for any missing inputs before preparing.
  2. 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.
  3. Avoid yes/no questions; favor ones that invite specifics, such as "what's slowing you down" rather than "is everything okay."
  4. Add guidance on handling sensitivities, such as how to ask about their manager without inviting a complaint session that undermines trust.
  5. 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."