Difficult conversation planner

1. Who, when, where.

Time, place, medium. Privacy matters; so does giving them a heads-up.

2. What is the conversation about, in one sentence?

3. What good looks like.

Two or three concrete outcomes you'd be happy with. Not “they agree with me” — something more useful.

4. Your part in the situation.

Where you contributed, even a little. Naming this early defuses 80% of defensiveness.

5. Their likely concern.

Steel-man their view. What is the smartest version of how they see it?

6. Opening sentence.

Short. Neutral. Signals it's a real conversation, not an ambush.

7. Three questions you can ask.

8. The line you won't cross.

A non-negotiable for you. Worth naming in advance so you don't negotiate it in the moment.