Challenge

I’ve been reflecting recently on coaching and AI, and I think the issue of challenge is one of the biggest downfalls, as highlighted in this article. https://www.ap.org/news-highlights/spotlights/2026/ai-is-giving-bad-advice-to-flatter-its-users-says-new-study-on-dangers-of-overly-agreeable-chatbots/

Learning to challenge appropriately in coaching is a skill and an art.

Challenging in the wrong way, or at the wrong time, can be damaging to the coaching relationship, leaving the client feeling judged or less confident.

But not being challenging enough can leave people trapped in a worldview that is keeping them stuck.

Done well, challenge can help people see their situation in different ways, opening up the scope for transformation.

Of course you can ask an AI to be more challenging – but it’s a a blunt tool. An AI isn’t watching to pick up the subtle signs that someone is too unsettled to be challenged further today. Or, on the flip side, to pick up the changes in tone which can mean someone is glossing over an assumption they haven’t examined.

A good coach will develop a sense of when someone needs to be challenged and how and when to challenge them. AI is growing fast, but I think the subtleties of human interaction will always be beyond its scope.