#111: The Practice of Curiosity and Why Leaders Default to Certainty
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A 360-degree review told Tyler Chisholm exactly what was wrong with his leadership: he filled every room, jumped to conclusions, and never let his team finish a sentence. His team had stopped contributing. They were just waiting to be told what to do.
In this episode of The Executive Commute, Jayson Krause talks with Tyler Chisholm, CEO and author of Curious as Hell, about the moment that feedback forced him to rebuild how he leads. Tyler unpacks the difference between the leader he was in the boardroom and the host he'd become on his own podcast, and how closing that gap turned curiosity from a personality trait into a daily discipline. They get into where curiosity actually helps, where it gets weaponized into control, and what it takes to build a team that feels safe enough to think out loud.
They cover:
- The feedback that forced a leadership reset
- Curiosity as a practice, not a trait: self, relational, and strategic curiosity
- How questions get weaponized to control instead of learning
- Where curiosity fails (and command and control takes over)
- A simple tool for pausing before you react
- What actually predicts whether a leader succeeds or fails
If your meetings go quiet the moment you start talking, this one's worth the full hour.
Follow Jayson Krause:
YouTube: / @jaysonkrauseleadership
LinkedIn: / jayson-krause
0:00 - Introduction
0:41 - The 360 Review That Changed His Leadership
3:43 - What Changed When "Podcast Tyler" Led Meetings
6:00 - Tracking Fixed vs. Growth Mindset After Every Call
8:41 - From Playful Trait to Deliberate Practice
10:05 - Why Tyler Wrote Curious as Hell
13:21 - Writing in Flow: AI as Collaborator
15:50 - The Self Curiosity the Book Forced to the Surface
17:31 - Defining Curiosity as a Leadership Practice
19:16 - The "No Time to Be Curious" Myth
22:03 - The Latin Root of Curiosity
28:44 - Weaponizing Curiosity
29:39 - Isn't a Leader's Job to Manipulate?
37:18 - Self Curiosity Comes First
39:19 - When Curiosity Isn't the Right Tool
42:17 - The Tactical Sigh
45:08 - Would You Rather: Curious vs. Safe to Be Curious Around
46:34 - Creating the Conditions for Curiosity
49:13 - The Nuclear Button
52:06 - The Cost of Reacting Instead of Leading
53:00 - True or False: Questions and Culture Health
56:02 - The Worst Advice About Curiosity
57:31 - "Tell Me More": Curious vs. Diagnostic Questions
59:38 - How to Know Curiosity Is Missing
1:02:42 - Know When to Call a Coach
1:04:51 - The Invisible Force Behind Leadership Success
1:06:26 - Closing Thoughts