How to use AI to prepare for a difficult conversation.

Rehearsing the conversation before you have it.

5/8/20261 min read

Most of us have a conversation we're dreading.

A talk with an adult child about a sensitive family matter. A discussion with a doctor about a diagnosis that frightened you. A negotiation with a contractor who hasn't done what they promised. A conversation with a neighbor that's been put off too long already.

These conversations are hard not because we don't know what we want to say, but because we don't know how the other person will respond — and we haven't thought through what we'll say when they do.

This is something AI can genuinely help with.

Here's how. Describe the conversation you're preparing for to your AI assistant. Explain who the other person is, what the situation involves, and what you're hoping to achieve. Then ask the AI to play the role of the other person — to respond the way they might actually respond — so you can practice what you'll say.

It sounds slightly unusual. But it works remarkably well.

If you're preparing to talk to a doctor, for instance, you might say: "I want to ask my doctor about switching my blood pressure medication because of the side effects. Can you play the role of a busy doctor who might be slightly resistant to changing a prescription that's technically working?" Then practice the conversation. See what comes up. Adjust your approach.

You can ask the AI to be more challenging, or more sympathetic. You can try the conversation several different ways. You can ask it afterwards what you might have said differently.

By the time you have the real conversation, you've already had it once. The surprise is gone. The anxiety is lower. And you're much more likely to say what you actually mean.

Preparation is one of the oldest tools for managing difficult situations. AI just makes it easier to prepare.

Our book 4, AI for Everyday Life covers this and many other ways AI can help with the conversations and decisions that matter most.