Your AI Coach: Accountability + Advisory Board That Pushes Back

This is a working AI coaching system you install in Claude. Not a PDF. Not a prompt library. A skill that configures itself around you and gets better every time you use it.

Daily Coach
A structured coaching session grounded in five real coaching traditions: Mochary Method, Bill Campbell's Trillion Dollar Coach, Marshall Goldsmith, The Coaching Habit, and Jerry Colonna's Radical Self-Inquiry. The coach checks in on how you're feeling, reviews what you committed to last time, helps you think through what's live, and ends every session with one specific push toward action.

This is not an AI that agrees with everything you say. It names avoidance. It closes the gap between what you say you want and what you actually do. It tracks patterns across sessions and escalates when the same issue keeps showing up.

Advisory Board
3-5 AI advisors built around your blind spots. Each has their own personality, expertise, decision-making style, and signature question. When you bring a strategic decision, they each analyze it from their lens, then debate each other before advising you.

If everyone agrees, the board forces a counter-argument. If three members disagree with your direction, you have to articulate why you're overriding them. The disagreement is the product.

What's in the download:

• Main skill file with all routing and session logic

• 5 coaching traditions reference with a when-to-use guide

• Personality diagnostic for coach calibration and board composition

• Board member archetypes showing what good advisors look like

• Full session structure for coaching and board meetings

• Voice rules that make the coach direct, specific, and honest

• Example sessions showing the coach and board in action

• Config folder that grows with you across conversations

Setup (5 minutes)
Install the skill in Claude. The first time you run it, the coach interviews you: what you do, what's keeping you up at night, how you process decisions, what kind of feedback actually lands for you. From your answers, it builds a personality profile, calibrates which coaching traditions to lean on, and suggests board members that complement your blind spots.

You approve or adjust. Then you're in your first coaching session immediately. No coming back later. The coach is live.

Daily coaching
Say "coach me" and the session runs: body check-in, commitment review, what's on your mind, targeted coaching from the relevant tradition, new commitments with specific dates, and one small push you can do in the next two minutes.

The coach tracks patterns. First time you avoid something, it names it. Third time, it changes approach. Seventh time, it asks what's really going on underneath.

Board meetings
When you've got a bigger decision, say "board meeting." Your advisors each analyze the situation from their domain. They present their positions, then debate each other. You ask questions. They walk you through each decision one at a time. You decide. They don't.

It compounds
Every session updates your config. The coach learns your patterns. The board accumulates context. The more you use it, the sharper the pushback gets.

• Decision-makers who work alone. Founders, freelancers, solo operators, coaches, consultants. You don't have a sparring partner. AI has been too agreeable to fill that role. This fixes that.

• Leaders who miss having someone who pushes back. You used to have a colleague or mentor who told you the truth. Now AI gives you the answer you wanted instead of the one you needed.

• Anyone who uses AI regularly and has noticed it agrees with everything. You've tried "be critical" in the system prompt. It doesn't work. This does, because the coaching traditions and voice rules are designed to produce genuine pushback, not performative disagreement.

• People who want accountability that compounds. Not a one-time exercise. A system that remembers what you committed to, notices when the same pattern keeps showing up, and changes its approach when the first one didn't work.

You don't need to be a PM. You don't need to be technical. If you make decisions and want a better thinking partner, this works.

This isn't a prompt you paste into ChatGPT.

Most "AI coach" products are a system prompt that says "be a coach" and a list of questions. They reset every conversation. They have no memory. They have no framework for when to push hard and when to ask a question. They agree with you within three exchanges.

This is different because it's built from a production system that runs daily. The coaching traditions are real frameworks used by real executive coaches. The voice rules were tested over hundreds of sessions until the AI stopped sounding like a chatbot and started sounding like someone who cares enough to be honest.

The advisory board concept comes from running a 5-person AI board for a year and learning what makes AI disagreement useful instead of annoying. The answer: each member needs a real belief system, a real decision-making approach, and constitutional rules that prevent them from blending into generic advice.

The pattern tracking is what makes it compound. A coach that resets every session is a novelty. A coach that remembers you avoided the same conversation three times in a row and asks "what's really going on?" is something you actually use.