KeynoteAICoaching practice

International Coaching Week, Singapore

What Happened When I Talked About AI at International Coaching Week Singapore

I did not go into the room expecting consensus. The session was called “The Augmented Coach: Amplify Your Voice with AI” and it was designed to do two things that do not always sit comfortably together: unsettle and inspire.

It did both. What I did not fully anticipate was how much the room wanted to talk.

The opening that set the tone

The session opened with a provocation. Not a question, not a poll: a scene. An AI holding complete attention for twelve minutes without once needing the client to like it. Without checking whether it had said the wrong thing. Without the ambient self-monitoring that runs underneath so much of what we do as coaches.

The question I asked the room was simple: what did that do to you?

That question stayed live for most of the fifty minutes that followed.

The part that triggered people

The middle section of the talk did not let coaches off the hook. It named the risk that most AI conversations in coaching circles avoid: that the biggest threat to our professional ethics is not malice but convenience. That the boundary between appropriate and inappropriate use of AI tools erodes gradually, through habit, not through a single bad decision.

The research on this is striking. A significant majority of people who worry about sharing sensitive data with AI tools do it anyway. Coaches are not immune to this dynamic. If anything, the intimacy of what we carry — client vulnerabilities, organisational politics, developmental hypotheses about people’s shadow sides — makes the stakes higher than in most professions.

Naming this directly created discomfort in the room. That was the intention. A provocation that produces comfort has not done its job.

The part that opened something up

The second movement of the session was different. Three live demonstrations of AI used not to replace coaching judgment but to extend it: a Hypothesis Challenger that generates alternative explanations for what a coach believes is happening with a client, including at least one that implicates the coach’s own blind spots; an Interference Detector that reads a session transcript for moments where the coach stopped following and started leading; and a Longitudinal Mirror that reads across months of session notes to surface the underlying narrative a client is unconsciously constructing.

Each demo was framed the same way: this is AI as the supervision you cannot always access. Not a substitute for a human supervisor, but a thinking partner available between the sessions when supervision matters most.

The room shifted here. Curiosity replaced defensiveness. Coaches started asking about their own practice, their own patterns, what they might see if they looked that closely at their own interventions.

The ending that stayed with people

The session closed with a polarity: Human Presence and AI Augmentation. Not a problem to solve but a tension to manage — two poles that need each other. Coaches were invited to physically voice each quadrant in the room: what we gain from full human presence, what we risk losing by over-relying on it, what AI augmentation genuinely offers, and where it goes wrong.

Something shifted in the room during that exercise. The conversation stopped being about AI and started being about practice. About what we are actually doing when we coach, and what we owe the people who trust us with their development.

The questions continued for days afterward. In the corridor, by message, from coaches who had gone home and started thinking differently about tools they were already using.

That is what a good provocation does. It does not close the conversation. It sends people back to their own practice with a question they cannot ignore.

International Coaching Week Singapore, May 2026. Session duration: 50 minutes. Approximately 60 participants from ICF chapters across APAC.

The prompts

All three live demonstrations used prompts you can run yourself in any AI tool. Start with the Hypothesis Challenger. It is the one most likely to show you something you would prefer not to see.

1. The Hypothesis Challenger

Most of us go into a session with a working theory. We do not always name it, but it shapes every question we ask. This prompt generates three alternative explanations — including at least one that implicates you.

Prompt A — The hypothesis

I am an executive coach preparing for a session tomorrow. My working hypothesis about my client is: [describe your hypothesis here].

Do not validate this hypothesis. Instead, generate the three most compelling alternative explanations for what I am observing, including at least one that considers my own possible blind spots or projections as her coach.

Be direct.

The instruction to be direct matters. Without it, AI defaults to being agreeable — which is useless for this purpose.

Prompt B — The follow-through

Now take the alternative explanation about my blind spot. If that were true, what would I need to do differently in tomorrow’s session? What questions am I probably NOT asking because of this bias? Give me three.

Now it is not about your client. It is about your coaching. That is the move.

2. The Interference Detector

We all have moments where we stopped following and started leading. We know this. We just do not always have the mirror. This prompt reads your transcript for coaching interference.

Prompt — Post-session transcript analysis

You are acting as Coach Supervisor. I am attaching a transcript excerpt from a coaching session. I am the coach. Analyse my interventions only, not the client’s material. Specifically:

(1) Identify any moments where my questions appear to lead rather than follow.

(2) Flag any moments where I may have collapsed the client’s thinking space by moving too quickly to interpretation or reframe.

(3) Note any linguistic patterns in my language that suggest my own frame or agenda may have entered the room.

Be honest. I am not looking for reassurance. I am looking for the feedback I would get from a senior supervisor who has no interest in protecting my ego.

Follow-through prompt

Based on the interference patterns you identified: what recurring coaching habit might these suggest? What might I be consistently doing across sessions that I am not aware of? Give me one honest hypothesis.

3. The Longitudinal Mirror

You are so close to the client — six months, twelve months — that you stop seeing the pattern. You need distance you do not have. This prompt reads across your session notes to surface what the client is unconsciously constructing.

Prompt — Cross-session pattern read

Below are anonymised notes from [number] coaching sessions with the same client over [timeframe]. Your task is not to summarise the content. Your task is to read for the underlying narrative — the story this client is unconsciously telling about themselves, about what is possible, and about their relationship to change.

Look for:

(1) Recurring language, metaphors, or images.

(2) What the client consistently moves toward and away from.

(3) What appears to be changing, and what appears to be staying the same despite apparent effort.

(4) Any discrepancy between what the client says they want and the world they appear to be constructing.

(5) Do not diagnose. Describe what you observe in the text.

Anonymise your notes before pasting them into any commercial AI tool. Client confidentiality is not optional.

Interested in bringing this session to your organisation or event?

Get in touch