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Stories / Work / Used AI to prep for a difficult conversaโ€ฆ
BH
Ben Hughes
July 12, 2026 ยท Work
SKILL LEVEL
Intermediate
AI TOOL
๐Ÿค– Claude

Used AI to prep for a difficult conversation with my business partner

My business partner and I had been avoiding a conversation about equity for months. He felt he deserved more. I disagreed. We were both anxious about it becoming a fight. I used Claude to roleplay the conversation first. I described the situation, our history, and where I thought the disagreement was rooted. Then I asked it to play my partner and push back on my position. It did โ€” convincingly. Going through it several times helped me find the weak points in my own argument, understand his likely perspective better, and figure out which points actually mattered versus which ones I was defending out of stubbornness. The real conversation still wasn't easy. But I was prepared. We found a solution in about an hour instead of it becoming a months-long standoff.

โฑ Time saved: Months of avoidance
โœฆ WORKFLOW STEPS
1Write down your position and the other person's likely position clearly
2Ask AI to roleplay the other person and challenge your view
3Notice where you struggle to respond โ€” those are your weak spots
4Revise your approach, then do another round
๐Ÿ“‹ THE PROMPT
I need to have a difficult conversation with [person] about [topic]. Here's the background: [situation]. Can you roleplay as them and push back on my position? I want to find the weak points in my argument and understand their perspective before the real conversation.

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