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June 22, 2026 25 mins

The more senior you become, the more dangerous certainty gets. That's the idea at the heart of this conversation with Dr Debra Clary. Most leaders are rewarded for having answers. The problem is that eventually the answers become the thing that limits the business.

What struck me most was the distinction between confidence and certainty. Confidence helps leaders make decisions. Certainty shuts down debate, curiosity, innovation, and often performance. We talked about why employee engagement is collapsing, how leaders accidentally train curiosity out of organisations, and why the businesses that keep asking better questions outperform those that think they've already found the answers.

In this episode

A reminder that your job isn't to have all the answers.

  • Bring the people closest to the problem into the conversation before making decisions
  • Delegate problems, not tasks
  • Create confidence without pretending to have certainty
  • Build a culture where new ideas are welcomed instead of defended against
  • Ask better questions because answers are increasingly becoming a commodity
Episode highlights
  • 03:20 Why the best executives listen differently when the pressure is highest
  • 05:35 The alarming message disengaged employees are sending leadership teams
  • 08:20 How organisations systematically train curiosity out of people
  • 11:10 Why AI makes questions more valuable than answers
  • 12:40 The leadership trap of looking confident by sounding certain
  • 18:55 The founder who discovered he was the reason innovation had stalled
  • 23:05 What AI might be doing to our ability to think for ourselves
Links and resources

Curiosity sounds soft until you realise how many business problems start when people stop asking questions. If you enjoyed this conversation, follow the show, leave a review, and share it with another founder, MD, or senior leader who might benefit from hearing it.

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