Plan a listening session or skip-level to uncover my team's real challenges
Questions and a plan for listening sessions or skip-levels that get honest answers about what's slowing your team down.
The prompt
Help me plan conversations to find out what is really getting in my team's way.
Team: [SIZE, functions, levels, remote/hybrid/on-site]
Format: [1:1 skip-levels / small group listening sessions / anonymous survey plus follow-up]
Why now: [e.g. "I'm new", "engagement scores dropped", "deadlines keep slipping", "after a reorg"]
What I suspect (and might be wrong about): [HYPOTHESES]
Trust level: [how candid people are likely to be with me, and why]
Give me:
1. How to open - a short script explaining the purpose, what I'll do with what I hear, and what stays confidential.
2. Question set (12-15), grouped by: day-to-day work and blockers, tools and processes, priorities and clarity, collaboration with other teams, workload and wellbeing, leadership (including me), and ideas. Include 2-3 questions that make it easy to say something critical (e.g. "What's one thing we do that wastes your time?").
3. Follow-up probes to get from complaints to specifics ("Can you give me a recent example?").
4. How to capture notes without making people guarded, and a simple template for grouping themes afterward.
5. Closing the loop: what to share back with the team, by when, including what I won't change and why.
Rules: neutral, open questions - no leading questions that confirm my hypotheses. Remind me not to defend, debate, or promise fixes in the room. If someone raises harassment, discrimination, or safety concerns, tell me to follow the formal reporting process rather than treat it as general feedback.
Highlighted [brackets] are blanks to replace with your own details.
Fill in the blanks and use this promptMore Leadership & Management prompts
What to fill in
- SIZE, functions, levels, remote/hybrid/on-site
- HYPOTHESES
- how candid people are likely to be with me, and why
How this prompt is built
This prompt follows the Few-Shot structure (Few-shot prompting). A few-shot prompt includes one or more worked examples of the input and the output you want, so the model can copy the pattern instead of guessing it.
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