How to Coach Your AI (So It Actually Improves)

🏆 “A good coach can change the game. A great coach can change your life!”

- Anna Meares, 4 time Olympian

Hello Reader,

After 4 weeks of hosting AI Coaching Power Hours in my new community, the Ai Coaching Academy, we've uncovered some best practices:

Provide specific feedback when responses aren’t satisfactory, guiding the AI to refine its output.
Break down complex requests into smaller, more manageable steps.
Use probing questions to help the AI dig deeper or explore alternative perspectives.
Be patient and iterative, treating the AI interaction like a collaborative coaching conversation.
Clearly articulate expectations and the measure of success for the task.
Give context and background information to help the AI understand the nuanced requirements.

The key is to be intentional, clear, and specific in your interactions, just as you would when coaching a human client.

(Academy Members can find all the Worksheets used in the replays.)

On of the best prompts we used during the AI Coaching Power Hours was the Canonical Context Session:

I want you to interview me in depth. Ask as many questions as you need to fully understand my business, my goals, my values, and how I think.

This conversation will be the canonical reference point for my work going forward. Any time I ask you to do something that requires deep context, strategic judgment, or alignment with my business, you should treat this thread as the source of truth.

Start by outlining a full list of in-depth questions you plan to ask me. Then ask me one-by-one in sequence.

You can use Voice Mode (video tutorial below) to narrate this prompt to an LLM. Then you can just answer the questions it asks, and request that it saves what it has learned to its persistent memory.

🛠️ DEMO: How to Use Voice Mode

This 4-minute video is one of the dozens of lessons in my Foundations of AI Certification.

Watch Now

📰 New AI News This Week

Openclaw (née Moltbot, née Clawdbot) gives an agent control of a machine, spawning pre-AGI vibes
Project Genie was launched for Google Ultra subscribers, allowing the creation and exploration of new worlds
UIPath projects that the 42% of APAC organisations using agentic AI will double by the end of 2026 to 86%

👓 What I’m Reading

Moltbook: The Social Network You Can't Join (Because You're Human)
Welcome to the Promethean Age: A Field Guide
The Wheel of Time series (my 7min video review is denser than all 14 books)

Are you ready to grow your AI capabilities?

Join me for one of my upcoming free events:

Thursday, February 5 at 10:00 AM GMT+13

Ai Coaching Power Hour

A weekly space to think better, together — with the help of AI. What happens when you blend human connection, coaching frameworks, and an AI that listens without judgment or ego? You get a power hour that jump-starts clarity, confidence, and momentum. Join Caelan Huntress for a monthly AI Coaching Power Hour.This session is designed to give you ...

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Monday, February 16 at 4:00 PM GMT+13

AiAmA with Caelan Huntress

What's stopping you? What's holding you back? What are you troubleshooting? In this interactive group coaching session, ask your questions and get some answers. See what others are struggling with, and learn about what your peers are working on.

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Friday, February 20 at 1:00 PM GMT+13

Create a Coaching Relationship with AI

AI is no longer a novelty skill. It’s become a practiced capability. The real AI advantage doesn’t come from knowing which tools exist. It comes from knowing how to think with them, reflect with them, and improve your judgment over time. In this hands-on, interactive session, hosted by Caelan Huntress, you’ll learn how to create a personal AI co...

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