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Difficult Conversation Prep

Prepare for a difficult conversation.

Answer five short questions. You'll get a structured prep sheet to read before you walk in the room — or before you send that message.

Question 1 of 5

Who is this conversation with?

Name and role or relationship (e.g. "Karim, my direct report" or "my co-founder").

Question 2 of 5

What is the core issue you need to address?

Be specific. One or two sentences. Don't worry about being fair yet — just say what's true for you right now.

Question 3 of 5

What outcome do you want from this conversation?

Not what you want to say — what you want to happen as a result. What changes, gets decided, or gets understood?

Question 4 of 5

What are you most worried about?

The reaction, the outcome, or your own behaviour. Whatever's sitting in your chest right now.

Question 5 of 5

What do you want them to know about your intent?

If they could hear one true thing before you start, what would it be? This often becomes your opening line.

Prep Sheet

Conversation with —

What this is really about
What you want them to know before you start
A way to begin
What success looks like
Your worry, named and ready
A note before you go in