The Hard Conversation — A 12-Week Masterclass in Negotiation and Difficult Conversations With an AI Tutor: Say the Thing, Keep the Relationship.

A masterclass you actually finish — because you spend it talking, not watching. This 12-week plan turns an AI tutor into the person across the table: the tough boss, the defensive colleague, the counterpart who won't budge. You rehearse the hard conversation safely, again and again, then the tutor drops character and debriefs what landed. By the end you can say the difficult thing and keep the relationship intact. Conflict-avoidant beginners welcome — freezing is where we start.

Format: A digital guide with twelve weekly sessions. You lead one fully scripted ~60-minute session each week — every step timed, every AI prompt written for you — with an AI coach that role-plays the other side and debriefs each rehearsal. No live sessions, no group calls, no expertise needed.

What you get

• A "Never used an AI chat assistant? Start here" onboarding that takes a complete beginner from zero to ready in about five minutes, using a free AI assistant — no paid plan needed.
• Four rescue prompts in the front matter for when a session goes sideways, you freeze mid rehearsal, or you need to reset.
• 12 deep weekly sessions, each built as a ready-to-run ~60-minute plan: a plain-language concept, a concrete worked example, a minute-by-minute session plan, copy/paste AI-tutor prompts at every step, a "show me" checkpoint you can only pass by holding the conversation, common mistakes to watch for, and practice reps.
• An AI-tutor prompt playbook — a Socratic starter that asks what you want first, a "make the other side harder" prompt, and a guardrail that keeps it honest (no manipulation, no memorized scripts).
• A two-question debrief habit you build by the end and run after any real conversation.

The 12 weeks

1. Why We Avoid the Hard Talk — and What It Costs
2. Separate the Person from the Problem
3. Listen to Actually Understand
4. Ask Clearly for What You Want
5. Give Hard Feedback So It Lands
6. Receive Criticism Without Getting Defensive
7. Say No and Set a Boundary
8. De-escalate Anger and Tension
9. Negotiation: Interests, Not Positions
10. Repair and the Real Apology
11. Project Week: Prepare and Have One Real Hard Conversation
12. Demo Day and the Debrief Habit

Who it's for

Adults who avoid conflict, freeze in negotiations, or dread giving and getting feedback — at work and in life. If you've been dodging a conversation for weeks, rehearsing arguments in the shower, or saying yes when you meant no, this is built for you. No experience needed; being conflict-avoidant is the starting line, not a disqualifier.

Why this instead of a free chatbot

A raw chatbot will hand you a script and cheerfully agree you're right. This pack ships the structure it lacks: a real 12-week progression, a tutor set up to play the other side for real — pushing back, getting defensive, holding leverage — so you rehearse under pressure instead of reading tips. It asks what you actually want before it coaches a single line, and it won't let you win at the relationship's expense. Reps against a tough counterpart, not confident guessing.

Format note

This is a paid digital guide framed like a masterclass — and built to feel like one you finish. The "classroom" is you and an AI tutor role-playing the hard conversation, one scripted ~60-minute session a week. The value isn't watching lectures; it's the reps you get saying the thing out loud before it counts — with every step and every prompt already written for you.

FAQ

• Do I need any experience? None. Week 1 is naming the conversations you've been avoiding; every skill is rehearsed in small, low-stakes reps before you use it for real.
• Which AI does it use? What if I've never used an AI chat assistant? It works with any modern AI assistant — ChatGPT, Claude, Copilot, Gemini. Free versions are enough; no paid plan needed. The guide's first section walks complete beginners through setup in about five minutes, so starting from zero is fine. Voice mode helps if you want to practice out loud.
• Is this about asking for a raise or money strategy? It's a communication and negotiation skills pack, not financial advice. When a week touches asking for more — a raise, a better deal — it trains only the conversation: making your case clearly and handling the response. No money management, no salary strategy.
• Will it just give me a script to memorize? No — that's the point. The tutor makes you find your own words by asking what you want and what you fear first, then role-plays so you earn the line by saying it under a little pressure.
• Refunds? Standard marketplace refund policy applies.

Get the whole track

Learning more than one hard skill this year? Get the whole adult toolbox — every adult-skills pack in one bundle.