Can AI Ask a Better Question? Coaching, Access and the Role of Technology with Sam Isaacson

In this episode of Secrets of Learning and Development, we’re joined by Sam Isaacson, coach, author and founder of an AI-powered coaching platform that is currently being piloted within the NHS and explored by several large organisations.

With a background in technology risk consultancy, Sam brings a unique lens to the evolving conversation around AI and coaching. He shares how his own shift into coaching sparked a deeper interest in human behaviour, and how this eventually led him to create a non-directive AI tool designed to open up coaching access to people who might otherwise never experience it.

We discuss:

The early pilots of his AI coaching platform, including work with NHS staff

• Why the platform never gives answers and instead focuses on asking thoughtful questions
• What it means to bring coaching into organisations as a scalable, reflective practice
• The role of choice, tone and trust in both human and AI-led conversations
• Why Sam believes good coaching, whether human or digital, starts with listening well

While opinions may differ on how far AI should go in the world of coaching, this episode offers space to consider the questions it raises. Sam shares his thinking with openness and clarity, giving listeners the chance to reflect on what might support or challenge their own views.

Key Learnings

AI can expand access to coaching, but it is not a replacement for human connection.
Sam is clear that his platform is not designed to replace human coaches. Instead, it offers a non-directive, reflective experience to people who would not otherwise have access, such as NHS staff or frontline workers. For some, the AI experience may be their first exposure to coaching-style questioning. The tool focuses on asking one thoughtful question at a time, rather than providing solutions, encouraging users to do the thinking themselves.

Measuring coaching impact matters and AI can help with that.
Drawing on his consultancy background, Sam questions why coaching often goes unmeasured. His platform incorporates self-efficacy and goal attainment metrics into the process, aiming to show tangible outcomes from reflective work. He argues that this kind of measurement strengthens the case for coaching as an organisational investment, rather than something optional or difficult to justify.

Guest information: 

https://isaacson.uk 
http://isaacson.uk/digital-and-ai-coaches-conference

https://www.aicoach.chat/
linkedin.com/in/samisaacson
https://tidycal.com/isaacson/intro

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Chapters

• 2:55 Introduction
• 4:21 What drew Sam from tech consultancy into coaching
• 7:44 Connect Coaching with AI Capability
• 14:59 The AI Coach and how it works
• 16:47 Pilots with NHS and other organisations
• 29:53 Sam's view on coaching philossophy