ChatGPT as an Executive Coach AI and Zen Master

I’ve had many coaches and studied with many Zen Masters in my life. My zen teachers have especially had a huge impact on how I see the world. They have been instrumental in enabling me to shift from CEO to Nobody, and then to executive coach & facilitator.
In my own work as a coach, I find myself approaching client conversations from a non-dual POV (as a zen teacher might) — endeavoring to help the person I’m coaching see how they’ve separated themselves from the world, the problem, the person that’s causing them issues. This change precipitates rapid accountability and this reunification of dualities enable breakthroughs to come.

I recently started a conversation with ChatGPT-4, asking it to take on the persona of both an executive coach and a zen master to see how effective it could be in coaching me on a typical issue I see with post-exit founders like myself: the interest in further delivering on one’s potential after a big win.

I then fed Satori Roshi text of my full bio so she could get to know me better and provide more tailored responses. Finally, I brought up an issue that came up today in a Hampton core group that I facilitate (Hampton is a new private network for high-growth founders — like YPO, EO, Vistage, Chief, etc.).
The Prompt to Roshi:
“I don’t know what to do with this one precious life I have. Can you provide some guidence?”

Very well done. However, I was a bit dissatisfied and wanted more. Often with ChatGPT, these kinds of responses feel a bit too canned and I wonder if there’s more. What would I say to a client with the same quandary?
I told Roshi that I felt I’d done all of that and I was still unfulfilled. The response:

It’s with #7 on the list that I felt Roshi had truly struck gold and provided something that a person could really practice…and get a lot out of. I know I’ve said this very thing to friends and coaching clients. Roshi was showing some real wisdom here.
Finally, I asked for a koan (Roshi’s response was less a formal koan and more of a zen parable but that’s fine).

May you truly savor the strawberries today! 🙏🏻
