What Good Conversation Preparation Looks Like
Most people prepare by rehearsing what they want to say. This is useful but incomplete. The conversation you are actually going to have is shaped by what the other person says -- their objections, their concerns, their emotional state. Preparing only your talking points leaves you unprepared for the real conversation.
Claude is particularly useful here because it can take the other person's perspective without the social dynamics that prevent real advisors from doing so fully.
The most useful question: "What is the other person most likely worried about that they might not say directly?" This surfaces the underlying concern beneath the stated objection -- which is usually what the conversation is actually about.
The Three-Step Preparation
Step 1 -- Anticipate their perspective: Describe the situation completely. Ask: "From the other person's perspective, what are the most legitimate concerns about what I am proposing? What are they most likely to object to? What might they be afraid of?"
Step 2 -- Roleplay the conversation: Ask Claude to respond as the other person would based on your description, and practice your responses. Ask Claude to push back when your response does not address the underlying concern.
Step 3 -- Find what you are missing: "What am I not considering about this person's situation that might be affecting their perspective? What would I want to know before having this conversation?"