What a world class restaurant taught me about building AI for coaches

In 2014, my wife and I had dinner at Eleven Madison Park in New York. I still remember how it felt. Not just the food, though the food was extraordinary. It was everything else. The way the team noticed small things about us. The way they turned a meal into something that felt like it was made just for us. My wife, who is not easily impressed by fancy restaurants, loved every minute of it.

I did not know it at the time, but that evening was engineered by Will Guidara, the man who took Eleven Madison Park from a struggling brasserie to the number one restaurant in the world. Not by reinventing the cuisine. By reimagining what it means to truly take care of people.

Fast forward to a few weeks ago. I was scrolling LinkedIn on a quiet Sunday and saw a post by Nathaniel Cole, who picked up Guidara's book Unreasonable Hospitality during his sabbatical. That post pulled me straight back to that dining room in Manhattan, and then down a rabbit hole into Simon Sinek's two conversations with Guidara on A Bit of Optimism, including a recent episode that asks the question I think about every day. What happens to human connection when AI can do almost everything?

I want to be honest about why that question keeps me up at night.

The number that changed how I see coaching

The average executive coach spends roughly 40 percent of their working hours on things that are not coaching. Session notes. Prep. Admin. Follow ups. Scheduling. That is two full days a week spent on work that, while necessary, is not the reason anyone became a coach.

Two days a week not spent on the thing that actually transforms people.

When I heard Guidara talk about his 95/5 rule, something clicked. His philosophy: manage 95 percent of your business down to the penny. Be disciplined, be efficient, be tight. But spend the last 5 percent foolishly, on things that create an outsized emotional impact. The piece of Basque cheesecake delivered to a guest's hotel room. The surprise sledding trip to Central Park for a family who had never seen snow. Gestures that cost almost nothing relative to the whole operation, and that people remember for the rest of their lives.

The maths is the same in coaching. The 95 percent, the notes and prep and tracking and nudges, is essential. But it is not what changes someone's career or life. The 5 percent is. And right now, most coaches are so buried in the 95 that the 5 gets squeezed out.

The scary question I cannot ignore

Here is the thing nobody in AI wants to say out loud. What happens when an AI coaching tool gets good enough that a client starts to prefer it?

I think about this a lot. Because if we are building an AI that learns a coach's way of working, captures their insights, and supports clients between sessions, the obvious next question is whether the client eventually stops needing the coach.

I do not think so. But not for the comforting reasons you might expect.

It is not that AI is bad at empathy, or cannot replace the human touch. Those are platitudes. The real answer is more interesting. AI is excellent at pattern recognition, consistency and availability. What it cannot do is be unreasonable. It cannot notice that a client's energy shifted when they mentioned their daughter. It cannot decide, in a split second, to throw away the session agenda and sit in silence for two minutes because that is what this person needs right now. It cannot send a handwritten note after a breakthrough, or recommend a book that has nothing to do with leadership and everything to do with what the client is actually going through.

Those are the coaching equivalent of the cheesecake in the hotel room. Creative, intuitive, and a little bit reckless. No model would suggest them. They are the reason clients come back.

The CoachNova cheesecake moment

Let me make this concrete.

One of the coaches testing CoachNova told us about a moment that stuck with her. She was preparing for a session and her prep brief surfaced a pattern she had not consciously noticed. Over three sessions, her client had mentioned feeling invisible at work in different ways, using different words each time. The AI caught the thread. The coach brought it into the session, and something broke open. The client cried. Not from sadness. From relief at being seen.

That moment did not happen because AI replaced the coach. It happened because AI handed the coach an insight she might have missed, and the coach did something deeply human with it. She leaned in. She trusted her instinct. She was unreasonably attentive.

That is the 5 percent.

We built CoachNova to handle the 95 so that moments like that happen more often, by design rather than by accident. Session notes ready within minutes. An AI that learns your approach. Prompts that keep clients engaged between conversations. All so that when you walk into your next session, you are not scrambling through notes. You are fully present. You are ready to be unreasonable.

The real question

Guidara said something on the podcast that I keep coming back to. No one who ever changed the game did so by being reasonable.

As coaches, you already know this. You chose a profession built on the belief that one human paying deep attention to another can change everything. That is, by most business standards, completely unreasonable.

The question is not whether AI will change coaching. It will. The question is whether you use it to become more efficient, or more human.

I know what scares me. That coaches will use AI to scale themselves thin, to see more clients with less presence, to optimise the humanity out of their practice. That would be the reasonable thing to do. And it would be a disaster.

We are betting on the opposite. More presence. More attention. More of the 5 percent that no one expects and everyone remembers.

Inspired by Will Guidara's book Unreasonable Hospitality and his conversations with Simon Sinek on A Bit of Optimism, including the episode on why humans still win in the age of AI.