This AI prompt preps you for a hard conversation, like asking for a raise or confronting a roommate. You give it what happened & what you want. It gives you an opening line, 3 questions for when the talk stalls & 3 phrases for when the other person gets defensive.

Prepare for a hard conversation

You walk into a tough conversation knowing what you want. You rarely think about what the other person wants. So when the other person gets defensive, they’re not ready. Some freeze. Some get angry. Some start backpedaling on the thing they came to say.

Asking for a raise. Confronting a roommate. Telling your partner something they don’t want to hear. The conversation goes sideways because you didn’t plan for their reaction.

This prompt tries to fix that.

Help me prepare for an important conversation.
Step 1: Ask me to share the context in 8-12 short bullets: who it's with, what happened, what I want, what I'm afraid of, and what a good outcome looks like.
Step 2: Write a clear one-paragraph opening statement in my voice using this structure: observation, impact, request. Then give me 3 questions to ask that move the conversation toward clarity, and 3 phrases to use if the other person gets defensive or vague.
Step 3: Give me a 60-minute prep plan: 3 quick exercises (each under 10 minutes) to calm my body, tighten my message, and rehearse. End with one sentence I can repeat right before I start.

The useful parts are buried under a template that doesn’t belong here.

Step 2 is the whole prompt. An opening line built on what happened, how it landed, & what you’re asking for. Questions that move toward clarity. Phrases for when the other person shuts down, gets vague, or gets aggressive. That’s specific. That’s the part people need.

Step 1 is fine. Dumping context in bullets gives the model something to work with.

Step 3 is filler. “3 quick exercises to calm my body, tighten my message, and rehearse.” The model will tell you to take deep breaths & do yoga poses (not really, but you get where I’m going). None of that helps you prepare for what your boss says when you ask for more money. Or what your partner says when you bring up something they thought was settled.

And the mantra. “One sentence I can repeat right before I start.” When was the last time you could repeat something in your head while someone else was talking? You’re either going to miss what they said or look like you checked out. Even worse, you’ve lost it.

The good parts don’t need any of this. They’re strong enough to stand alone.

The prompt that preps you for a hard conversation

Conversations never go according to plan. That’s why you don’t want a script. You want a framework: how to open, & what to do when it goes sideways.

I need to prepare for a conversation with [WHO] about [WHAT].
Here's what happened: [CONTEXT]. What I want out of this: [GOAL].
What I'm worried about: [FEAR].

Write me an opening line: what happened, how it affected things, & what I'm asking for. Keep it under 3 sentences.

Then give me 3 questions to ask if the conversation stalls or gets vague. And 3 phrases I can use if they get defensive.

Don't give me a script. Give me a starting point & a plan for when it goes sideways.

The best conversation prep is knowing how to start & having a fallback for when it doesn’t go the way you planned. Nothing more.

When the conversation is a meeting, a message or a request

If it’s a meeting & you want to understand their side first, the meeting prep prompt works through what they might be worried about. If they already sent you something tense, the angry message prompt finds the real problem under the tone. Asking for something? The say yes prompt helps you make the ask.

This teardown first ran in issue 3.