Prepare for a Difficult Conversation
Draft talking points for a hard conversation (a raise ask, a disagreement, giving feedback).
Use case
Use before a conversation you're anxious about, to organize your thoughts and anticipate pushback rather than winging it.
Customize
Preview
I need to have a difficult conversation with {counterpart} about {topic}. My goal for the conversation is {goal}. I'm worried they might respond by {anticipated_pushback}.
Help me prepare: (1) an opening line that states the topic directly without being harsh, (2) 2-3 key points I should make, in order, (3) a response to the anticipated pushback that doesn't concede my goal, and (4) a way to close the conversation that's clear about next steps. Keep the tone direct but not confrontational.Usage guidance
Naming the specific pushback you're anticipating (not just "they might get defensive") gets you a much more useful prepared response than a generic de-escalation script.
Example input
Counterpart: my manager. Topic: asking for a title change without a raise (budget frozen). Goal: get agreement in principle, to be formalized next review cycle. Anticipated pushback: "let's revisit this later."
Example output
Opening: "I wanted to talk about my role and where it's headed — not compensation, just leveling."...
Last updated Jan 1, 2026
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