Using AI to Prepare for Difficult Conversations Course

No magic wand exists for difficult conversations, but this course comes close. Using Claude and other free, publicly available AI tools as a personal preparation coach, you will learn how to prepare for and navigate the conversations many people avoid, delay, or mishandle at work and in everyday life.

Difficult conversations rarely get easier by waiting. Going in unprepared or relying on language that does not sound natural to you can make them even harder. Whether you are addressing a performance issue, navigating conflict with a peer, delivering feedback to someone who struggles to receive it, preparing for a high-stakes conversation with leadership, or working through a difficult situation outside of work, this course offers a clear, step-by-step approach to using AI effectively.

You will learn how to prompt AI in ways that reflect your voice, anticipate how others may respond, and give you space to practice before the real conversation. You will leave with a personalized plan and a practical approach you can use whenever a difficult conversation arises, whether in the workplace or in daily life.

What You Will Learn

• Prompt AI effectively to get coaching-level guidance, not generic advice.
• Build a personal communication style profile so AI output sounds like you.
• Anticipate how the other person is likely to respond in a difficult conversation and prepare for it.
• Craft and refine an opening and approach that invites rather than inflames.
• Practice live using AI role-play and debrief your own performance.
• Leave with a complete, personalized conversation plan for immediate use.

Course Outline

Module 1: Why AI? Setting the Stage

• The avoidance cycle and what it costs us.
• What AI can and cannot do in conversation preparation.
• Overview of tools: Claude, ChatGPT, Gemini, and Pi.
• The personalization gap and why generic prompts produce generic results.
• Your first prompt, including unguided practice and debrief.

Module 2: Teaching AI Who You Are

• The four dimensions of communication style: directness, warmth, formality, and emotional expression.
• Building your Communication Style Profile.
• Putting your profile to work through before-and-after comparison.
• Common profile mistakes and how to fix them.

Module 3: Teaching AI About the Other Person

• Why the other person's profile matters.
• Building a Person Profile, including style, triggers, interests, and what makes them receptive.
• Using AI to anticipate reactions and stress-test your approach.
• Understanding the limits: AI sees only your perspective.

Module 4: Preparing Your Opening Statement

• The three-part anatomy of an effective opener.
• Five common opener mistakes and why they backfire.
• Drafting multiple versions with AI feedback.
• Refining your opener through iteration and peer review.

Module 5: Practice Mode — Role-Playing with AI

• Why practicing a conversation is different from rehearsing a monologue.
• Setting up a realistic AI role-play.
• Running a five-exchange practice simulation.
• Debriefing with AI: what you noticed and what to adjust.

Module 6: Your Personal Conversation Plan

• The six-part Conversation Plan framework.
• Building your plan with AI section by section.
• Using AI after the conversation through the post-conversation debrief prompt.
• Closing reflection and next steps.