Coaching and AI

Let’s start with the most important thing: your confidentiality is sacred.
Nothing you share will ever be fed into an unwalled AI tool without your explicit permission. Your thoughts belong to you, not to a server farm or a language model.

Now, a confession: I don’t know exactly how AI will change coaching. I’m just certain it will. So I’m committed to experimenting and reflecting in order to help you better.

What does that look like in practice? Again, I don’t know for sure. I’ll keep this page updated along my learning journey in the spirit of transparency.

  • Update #1 / AI to reflect on becoming our future self (September 11th, 2025): The vibe-coder is cliche; non-technical people furiously typing at a robot to build a billion dollar app. Well, in my experience, purely vibe-coding can’t build a full-fledged app yet, but it can be build a powerful story-telling tool. In Reaching Your Peak, I built out an interactive story book that prompts users with questions on what’s holding them back from becoming a better version of themselves. After they complete the story, an AI-rendered voice of mine reads it back to them.

Here’s what I’ve seen thus far:

  • AI for context (this works!): The same phrase can fall flat or strike like lightning depending on who says it. If you give me explicit permission to use some anonymous background information, like the books you love or the people you admire, I’ll be able to ask resonant questions quicker.

  • AI images as a mirror (this works!): When we feel something that we can’t quite put to words, sometimes the best thing to do is to stop trying to put it into words. AI allows all of us to be artists, even if not very good ones. I’ll invite you to describe how you're feeling, identify the root cause, and then have AI generate an image that captures that emotional state. I know it sounds silly but it’s often disarming, insightful, and strangely moving. The image becomes a mirror and a tool for deeper conversation.

  • AI as a coaching first step (this doesn’t work…yet?): I’ve tested dozens of coaching prompts to see if AI would be able to identify the proper jumping off point for a conversation. So far, I’ve personally found the AI coaching to be just kind of vanilla and blah. That said, I imagine that will change in the coming years. More on that in a separate blog post soon.

Above all, know this: I don’t see AI as a replacement for human connection. I see it as a tool which, when used thoughtfully, can help us go deeper into the heart of what matters most to you.