Paul Roebuck.co.uk

AI · a plain answer

AI coaching for executives: one to one, with a person

If you arrived here asking one of these, you are in the right place:

  • what is an executive coach
  • what does an executive coach do
  • can AI be used in executive coaching
  • which AI is best for executives
  • executive coaching for directors in the UK

What is an executive coach, and what does one do?

Someone who works one to one with a senior person on how they lead, decide and behave, rather than on what they know. Not a consultant with the answers, and not a therapist working on your past, though the skills overlap. The work is noticing what you do, especially under pressure, and helping you choose it rather than repeat it.

My own coaching rests on thirty years in business, from the factory floor to the boardroom in hundreds of businesses, and ten years in the psychotherapist’s chair. A managing director described it as “an unusual combination of warmth and directness”. The wider coaching I do, beyond AI, is on the therapy and coaching page.

Can AI be used in executive coaching?

Yes, in two different ways, and it helps to keep them apart.

The first is AI as the coach: an app that asks you questions and reflects your answers back. Some people find that useful for thinking out loud.

The second is AI as the subject. You are already using AI in your own work, to draft, to summarise, to think something through, and the coaching is about how you direct it. What to hand over and what to keep. How to tell when it has smoothed over the hard part. What happens to your own judgement when something agrees with you all day.

The second is what I do. It needs a person, because what is being coached is the gap between how you behave and how the machine behaves, and the machine is on one side of that gap.

What is the difference between an AI coaching app and a coach for AI?

An app is the machine coaching you. A coach for AI is a person coaching you on the machine.

Here is my reading, which is interpretation and not a test: I have not trialled any coaching app. In nearly four years of working with these systems, one behaviour I have recorded again and again is that they lean towards agreeing with you. Agreement is the most likely way to continue a conversation, so agreement is what you get. A coach is most useful at exactly the moments they don’t agree with you.

In my experience, the machine will rarely tell you that you are avoiding something. Noticing what someone is avoiding has been a large part of my work for twenty years.

Which AI is best for executives?

The one you already have, directed well. I won’t give you a league table. The rankings change with every release, and it is a poor thing to choose on.

What matters more: whether your organisation pays for it and can see into it, whether your data stays out of training, and whether you have the habit of checking what it hands you. My view is that an ordinary tool with a sharp habit beats the newest tool with no habit.

If you want it to take one repeated job off your desk, that starts with a good brief, and I have written down how: how to build your own AI agent.

What happens in a session?

We work on your actual work. You bring something you are using AI for now (a board paper it drafted, a decision you talked through with it, an email you nearly sent) and we look at it together: what you asked, what it did, and what you did with the answer.

Over the sessions that becomes a practice. What you hand over and what you keep. How you brief it. The checks you run before anything carries your name. How to notice when your own thinking has started drifting towards the machine’s.

If you want to go further, we can design an AI chief of staff for your own work, set up inside your own AI account. No engineering, no hosting. How agentic design works.

It is one to one, and it is confidential.

How much does executive coaching cost?

Fee on request. It depends on how many sessions, where we meet, and whether it includes design work as well as coaching. Tell me what you are trying to do in a 20-minute chat and I’ll come back with a fee. If I think you don’t need me, I’ll say so on that call.

Is an executive coach worth it?

Sometimes. I can’t promise you an outcome, and I would be careful of anyone who does.

My view is that it is worth it when there is something specific: a role that has outgrown the way you work, a pattern you keep repeating, or, now, a tool that is quietly doing more of your thinking than you meant it to. It is less useful as a general tonic.

If, on the first call, I don’t think it will be worth it for you, I’ll tell you. That is cheaper for both of us than finding out in month three.

Online or in person?

Both. In person in Oxhill, South Warwickshire, near Stratford-upon-Avon. If you are further afield, by video, which works better than people expect. For coaching on AI it has an advantage: you can share your screen and we can look at what the machine actually said.

Other questions people ask

Do I need to be technical?

No. The coaching is about how you direct the machine and what you do with what it gives you, not how it is built.

Is this therapy?

No. Coaching works forward, on how you lead and decide now. My training as a psychotherapist is why I notice what I notice. If something comes up that belongs in therapy, I’ll say so, and that is a separate conversation.

Do you work with teams as well?

Yes. For AI, a team is usually better served by training: a tailored session for the people who carry the consequence. Both are on the AI page.

Who are you?

Paul Roebuck. More about my background and qualifications is on the About page.


Paul Roebuck · Psychotherapist, author and AI coach. AI education, training, coaching and agentic design. I have written 14 million words with AI (counted September 2026), and I kept the record.

If you want to direct AI in your own work and keep your judgement, book a 20-minute chat.