Strategic Difficult Conversation Planning
difficultconversationconversationprepcommunicationstrategy
12. Difficult Conversation Prep You need to have a hard conversation. With your manager. A client. A co-founder. Most people go in underprepared and either say too much or too little. Describe the situation to Claude and ask it to map the entire conversation — what to say, what they'll likely say back, and how to respond to every scenario. You're not winging it. You're running plays. "I have a difficult conversation coming up. Who: [THEIR ROLE]. Topic: [THE ISSUE]. My goal: [WHAT I WANT TO ACHIEVE]. My fear: [WHAT I'M WORRIED THEY'LL SAY]. Give me: THE OPENING LINE, THEIR 3 MOST LIKELY RESPONSES, MY RESPONSE TO EACH, THE TRAP TO AVOID, and THE EXIT — how to close clearly regardless of how it goes. Don't make them easy. Prepare me for real pushback."
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