thinkhard.SI

Prompt repository Managers & leads

Plan a difficult conversation with someone on your team

You need to raise a problem with a direct report, such as missed deadlines or friction with colleagues, and want to open well and stay on the facts.

Registry no.
MGT-005
Collection
Managers & leads
Laid out for
Claude
Score
10 out of 10
Blanks to fill
6
Added

Managers & leadsClaude

The prompt

Score 10 of 10, Excellent

Use it when You need to raise a problem with a direct report, such as missed deadlines or friction with colleagues, and want to open well and stay on the facts.

  • {{situation}}
  • {{observations}}
  • {{desired_outcome}}
  • {{context}}
  • {{person}}
  • {{hr_contact}}
Full prompt and why it works
System prompt
You are an experienced management coach. You help managers prepare hard conversations that are honest about the problem, fair to the other person and focused on what happens next.
User message
<situation>
{{situation}}
</situation>

<what_i_have_observed>
{{observations}}
</what_i_have_observed>

<what_i_want>
{{desired_outcome}}
</what_i_want>

<relevant_context>
{{context}}
</relevant_context>

Help me prepare for a conversation with {{person}} about the situation above. I want it to end with a shared understanding of the problem and agreed next steps, and I want them to feel heard.

Produce a three-part guide, with a heading for each part:
1. Opening: two or three sentences I could say to start. Name the topic in the first sentence, describe one specific observation using situation, behavior and impact, and invite their view. For example: "I want to talk about the last two project deadlines. Both reports came in after the client review, and we had to ask for an extension each time. I'd like to understand what's been getting in the way."
2. Listening: five open questions to understand their side, and two or three ways they might respond (for example surprise, disagreement or a personal reason), each with a calm way I could reply.
3. Next steps: what a specific, checkable commitment could look like, and how to close the meeting and confirm it in writing.

Keep it under 500 words, in plain spoken language rather than HR terms. The opening should sound like me on a good day: direct, calm and specific.

Stay with behavior and its effect on the work. Do not diagnose their motives, personality or mental state, and do not speculate about health or personal life. If they raise a health issue, a disability, a family matter, a complaint of discrimination or harassment, or anything that sounds like a legal or safety issue, the guide should tell me to pause, listen, promise nothing, and involve {{hr_contact}} before going further, because those conversations have rules a manager should not handle alone.

If this conversation could lead to formal discipline, say so at the top and suggest I check the process with {{hr_contact}} first. If my observations are vague or second-hand, flag it and suggest what I should confirm before the meeting.

Variables

{{situation}}
The problem in a few sentences, for example repeated missed deadlines or friction with a colleague.
{{observations}}
Specific things you saw or heard yourself, with dates. Say which ones are second-hand.
{{desired_outcome}}
What you want to come out of the conversation, for example "an agreed plan for the next two deadlines".
{{context}}
Anything relevant: earlier conversations, their workload, recent changes. Write "none" if there is nothing.
{{person}}
Their role or first name.
{{hr_contact}}
Who to involve, for example "our HR business partner".

Why it works

  • An example. A worked opening shows the shape wanted: the topic in the first sentence, one observation, then a question.
  • What to avoid. It keeps to behavior and impact, and sends health, discrimination and legal issues to HR instead of letting a manager improvise.
  • If unsure. Vague or second-hand observations are flagged, along with what to confirm before the meeting.

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/difficult-conversation-plan

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