Meeting an AI Business Coach

An act of self-love or self-sabotage?

About a year ago, I interviewed one of the world’s most famous and prolific executive coaches. I wanted to talk to him about his art collection, which I’d heard was outstanding. But he didn’t want to talk about that. He wanted to talk about his personalized AI. He had spent, he said, over a million dollars training it on all of his writings—and he insisted that I try it. I did.

What emerged surprised me. Generic. Bland. Impersonal. It felt like a reasonably well edited compilation of truisms.

If he had been a gung ho tech bro, I wouldn’t have been so surprised. But this came was from someone who was supposed to understand human communication at a deep level. To appreciate that the heart of a coaching conversation is not what the coach says but what happens between coach and client. That, at its best, coaching (or mentoring) is about a relationship, not an information exchange.

We’d agreed to talk about art, not AI – and would have done so had his enthusiasm for his new tech not overwhelmed our conversation. So I let him talk. What I was left with was not just a sense of the absurd but some underlying, disquieting assumptions.

At any one time, I mentor CEOs or senior leaders of very large, usually global businesses. I also mentor a few entrepreneurs. I’ve worked in both settings and the contrast is always interesting and complimentary. In both cases, I frequently think that the biggest gift I provide is time to think. This is what leaders are paid for but their diaries rarely give them the time. Our appointments ensure that the thinking is scheduled. And thinking with a partner who can challenge, question, and draw connections can be much more valuable, and enjoyable, than thinking alone. That I don’t work in the business gives me a degree of objectivity and my experience, running other businesses and working with other clients, gives me a different perspective.

But what I don’t offer is a prescription or an orthodoxy. In the best conversations I have, clients find their own solutions to their concerns—theirs, not mine. No two companies are the same. No two clients are the same. If I found myself asking generic questions or dispensing generic advice, I’d know it was time to quit.

What makes the relationship flourish? Consistency—those monthly meetings—provides momentum. The appointment is a human commitment between us. The degree to which clients are supported by their peers or direct reports in aspects of their own performance makes a huge difference to their development. So those colleagues are invisible but influential participants in the process. It goes beyond the conversation between us.

So no two sessions are the same. For the simple reason that the context in which the company operates keeps changing. This can be on a global scale—tariffs, wars, competitors, financial crises, elections—and on a personal scale: problems at home, new hires, job losses, weather, marriage, kids, parents. Whole people do these jobs and the available data is uncoded and deeply ambiguous. A rich blend of the cerebral, the emotional, the professional and the personal that is unique—and keeps changing. Much about business is written as though it were context free: efficiency is always good, cutting costs never fails. But context is at least half of the puzzle. And it’s one reason management isn’t a science: you can’t do the controlled experiment between perfectly matched companies, markets, products. So you cannot know whether what worked last time is sure to work now. It takes imagination, re-calibration, experimentation and argument.

It is clear that time spent with another person who cares and pays attention—in any capacity—makes a measurable difference to how people feel about themselves. One useful analogy here is an experiment done into the placebo effect. In this study of patients with severe back pain, it was shown that placebos gave previously incapacitated patients the ability to leave the house and move around freely. That much was fairly predictable. But what yielded additional improvement? More time with a doctor. Longer consultations produced even better outcomes.

However much we may think of companies as being like factories and their workers akin to machines, the reality is that the richness and complexity of work is more organic than mechanical. That’s one reason we talk about organ-izations. Those within them are humans who benefit from connection, collaboration, feeling heard and understood. That seems blindingly obvious, but in case it isn’t, recent research from Gallup reflects this: AI is most productive when supporting people, not replacing them.

I was told that one tremendous advantage of the artificially intelligent coach was that it could continue to work after the human coach died. I can imagine a support team constantly retraining it on business news. But how would the coach evolve? Respond to the emerging environment? Who would decide on the updates? What would Smith, Keynes, Hayek or Chandler say today? It is literally unknowable—not least because as human beings we continue to change until the moment we die. And that includes changing our minds. Eternal verities in the business world? If only….

I can’t help but find the hubris of the immortal coach breathtaking. But it’s telling too, revealing an incapacity to recognize that wisdom is the intersection of thought thought and time. If you had asked, at the end of the 19^th century, which was the greatest of Shakespeare’s plays, King Lear wouldn’t have made the shortlist. It was rarely performed after Shakespeare died: too dark, too gruesome, too difficult. Until the 20^th century, with its world wars and genocides, made it the play for a radically altered audience. The alchemy of wisdom lies not in its words but in the hearts and minds that receive or reject it.

If You Want to Go Deeper

You might enjoy this piece on the power of awe.

For the Joy of It

Found wandering the streets of London this spring.