Difficult conversation planner

Spending 20 minutes planning a hard conversation is the difference between “that went better than expected” and “why did I say that.” Use this once per conversation you've been avoiding.

Related micro-course

When to use this

Before a conversation you've been avoiding for more than two weeks.
When the conversation has stakes (work performance, breakup, money, family) and you want to do it once, well.
When previous attempts have escalated and you want a different opening.

How to complete it

Write the three parallel stories from the brief (what happened / feelings / identity) before you draft the opening.
Plan the first sentence. The rest will flow; the opening usually doesn't.
Identify one thing you're willing to be wrong about before you walk in.

Common mistakes

Skipping the ‘what's your contribution’ section. Most failed difficult conversations are missing this.
Treating the planner as a script rather than as a rehearsal — reading from a script reliably feels manipulative.
Picking the wrong setting: in front of others, when drunk, in the doorway as someone's leaving.

Difficult conversation planner

Vinthony Academy · vinthony.com

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.