Workbook
The Difficult Conversation Workbook
Scripts, Prep Sheets, and Practice for the 20 Conversations Everyone Avoids
The conversation does not get easier while you wait. It gets older.
For the person who has been rehearsing a specific conversation for months and wants a written preparation document, not more anxiety.
The Name It First Experience
You already know which conversation you have been putting off. It lives at the back of your mind — in resentment, missed understanding, the low-grade cost of a thing that needs to be said. Your Conversation Prep Portfolio covers money, inheritance, estrangement, and the things you need from the people closest to you. For each one, you write what you want to say, what you fear, and the specific sentences you need. The output is not catharsis. It is a signed preparation document.
You can opt into 30-, 60-, and 90-day check-ins from your account. We recommend you do — the point is to see what changed.
Sample questions
- What difficult conversation have you already had successfully — the one where you said the hard thing and the relationship survived or improved because of it?
- What conversation are you currently avoiding — the one you know needs to happen but that you keep circling rather than starting?
- What would The Conversation Prep Sheet for this specific conversation say — what do you need to know about what you are trying to say, what you are afraid of, and what outcome you actually want?
Research basis
Grounded in Crucial Conversations research (Patterson et al.) on high-stakes communication / Nonviolent Communication (Rosenberg) on needs-based language for conflict / and research on avoidance coping and its relationship to relationship dissatisfaction (Christensen & Jacobson).
Choose your format.
Every format asks the same questions and produces the same document.
Print Paperbackpersonalize
A real book and a pen. Write in the margins. The most permanent version of you on a page.
$22.99
eBook + journal
The full guide on any screen, with a companion journal to write your answers by hand.
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Audiobook
We read every question and every scenario aloud. For the commute, the walk, the dishes.
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Hardcoverpersonalize
The keepsake edition — sewn, ribboned, made to sit on a shelf and be returned to.
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Digital Fill + membership+membership
Answer on screen. Your responses save as you go and assemble into your finished document.
$12.99
Hands-Free Interactive + membership+membership
Listen to each question and speak your answer. We capture it. You never touch a keyboard.
Not available
Everything packages
The Paperback Everything Package
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The Hardcover Everything Package
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The Premium Hardcover Everything Package
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Choose your pace.
The Essential path takes you to your finished document by the questions that matter most. The Full-depth path walks every question, every scenario, every angle. Both produce the same signed document — one just goes deeper on the way there.
Essential path
Shorter sessions. The questions that go directly to the document.
Full depth
Every question. Every scenario, every angle.
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