thinkhard.SI

Prompt repository Managers & leads

Prepare a skip-level meeting with people two levels below you

You manage managers and want honest, useful conversations with the people on their teams without going around them.

Registry no.
MGT-022
Collection
Managers & leads
Laid out for
Any chat model
Score
10 out of 10
Blanks to fill
6
Added

Managers & leadsAny chat

The prompt

Score 10 of 10, Excellent

Use it when You manage managers and want honest, useful conversations with the people on their teams without going around them.

  • {{attendees}}
  • {{their_manager}}
  • {{format}}
  • {{reason}}
  • {{context}}
  • {{hr_contact}}
Full prompt and why it works
Prompt
Help me prepare a skip-level meeting with {{attendees}}, who report to {{their_manager}}, who reports to me. I want to hear how the work is really going, spot problems early and build trust, without undermining their manager.

Format and length: {{format}}
Why I am holding it now: {{reason}}

What I already know about this team and anything I want to understand better:
"""
{{context}}
"""

Produce, with a heading for each part:
1. A note to {{their_manager}}, under 80 words, explaining the purpose so the meeting does not feel like an audit of them.
2. An invitation to the attendees, under 80 words, saying what the meeting is for and what it is not.
3. An opening I can say in under a minute, including what I will do with what they tell me.
4. Eight to ten open questions in a sensible order, starting easy, including at least two about obstacles and one about what I or leadership could do better. For example: "What is one thing that slows you down that you think I might not know about?"
5. How to close and follow up: what to commit to, and how to share themes with {{their_manager}} without naming who said what.

Keep it under 550 words, in words I could say out loud.

Do not include questions that ask people to rate or criticize their manager directly, because skip-levels that turn into manager reviews damage trust on both sides. Do not suggest promising changes in the meeting itself.

The opening must not promise complete confidentiality. If anything raised could be harassment, discrimination, a safety issue or another matter that needs a formal process, I have to pass it to {{hr_contact}}, so part 3 should say that plainly. If my context does not say whether this is a group or one-on-one meeting, plan for a group and note what to change for one-on-ones.

Variables

{{attendees}}
Who you are meeting, for example "the five analysts on the reporting team".
{{their_manager}}
Their manager's role or name, for example "the reporting team lead".
{{format}}
Group or one-on-one, and how long, for example "group, 45 minutes".
{{reason}}
Why now, for example "regular quarterly skip-levels" or "two resignations this quarter".
{{context}}
What you know about the team's work and anything you want to understand better.
{{hr_contact}}
Who handles formal concerns, for example "our HR business partner".

Why it works

  • Who it's for. A note to the team's manager comes first, so the meeting builds trust in both directions instead of feeling like an audit.
  • What to avoid. It leaves out questions that ask people to rate their manager, which is how skip-levels most often go wrong.
  • If unsure. The opening never promises full confidentiality, because harassment, discrimination or safety issues have to go to HR.

How to use it

  1. Press Fill in variables and type your details into each blank. What you type stays in this browser.
  2. Copy the filled prompt into the AI tool you already use, such as ChatGPT, Claude or Gemini, or open it in the Grader or the Prompt Tester here.
  3. Before you rely on it, try it on three or four real examples. The Prompt Tester runs them all at once and shows which ones go wrong.
Use it from code

Get this prompt as JSON from the free REST API, with your own text in the blanks, or let an AI assistant fetch it through the MCP server. No key.

curl -s https://thinkhard.si/api/v1/prompts/skip-level-meeting-prep

With the MCP server added to Claude, ChatGPT, Cursor or VS Code, call get_prompt with {"prompt": "skip-level-meeting-prep"}, or just ask for it by name.