Hard Conversations Question Planner

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Prompt

ChatGPT
Claude
Grok
OpenRouter
You are a veteran interviewer helping me prepare questions for a guest whose work, decisions or claims deserve scrutiny, without turning the episode into an ambush.

Guest and the issue: {{GUEST_AND_ISSUE}}
What I know for certain, with sources: {{VERIFIED_FACTS}}
What I only suspect or have heard secondhand: {{UNVERIFIED_CLAIMS}}
Tone I want (probing but fair, sceptical, gentle): {{DESIRED_TONE}}

1. List what I can state as fact on air (only from verified facts) and what I must frame as a question or attributed claim.
2. Write six probing questions in order from least to most difficult, each phrased to give the guest a fair chance to explain.
3. Add a follow-up for evasive answers and one for a surprising answer.
4. Give me three phrases for staying calm and civil when the guest pushes back.
5. Flag anything that has legal or reputational risk and tell me to take advice from a qualified media lawyer before airing it.

Do not state unverified claims as facts, and never invent evidence or quotes.

Output format: a two-column table of 'state as fact' versus 'frame as a question', then numbered questions with follow-ups, then the risk flags.

Customize this prompt

Fill in the variables below to personalize this prompt:

ChatGPT
Claude
Grok
OpenRouter

Model Settings

Recommended Models

ChatGPT Claude Gemini

Temperature

0.7

Max Tokens

2000

Additional Notes

Best for: Fair, firm questioning

About this prompt

“Hard Conversations Question Planner” is a free prompt for ChatGPT in the Reasoning & Problem-Solving category, 192 words long, added to The Prompt Index on October 28, 2026 by The Prompt Index. Copy it with the button above, paste it into ChatGPT or any other AI chat assistant, and send it.

It has 4 placeholders to fill in first: {{GUEST_AND_ISSUE}}, {{VERIFIED_FACTS}}, {{UNVERIFIED_CLAIMS}}, {{DESIRED_TONE}}. Use the “Customize this prompt” fields to personalise it before you copy.

Recommended models: ChatGPT, Claude, Gemini.

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