The Curious Leader: Tyler Chisholm on Why Asking Beats Knowing

There is a quiet myth most leaders inherit before they ever sit at the head of the table: that they are supposed to have all the answers. Show up sharp. Speak with certainty. Move quickly. Anything less is weakness. And yet, the leaders who actually build trust, retain great teams, and adapt under pressure tend to do the opposite. They ask. They pause. They sit with not knowing.

In this BizBlend conversation, host Sana sits with Tyler Chisholm, CEO of Clearmotive Marketing, author of Curious as Hell, and host of more than 650 podcast episodes, to unpack why curiosity is the most underrated leadership skill of our time. Tyler walks through his three-tier framework of self, relational, and strategic curiosity, traces the moment his own command-and-control style stopped working, and shares the deliberately old-school exercise he used to retrain his leadership instincts. A grounded listen for any leader who is tired of pretending to have it all figured out.

About the Guest:

Tyler Chisholm is the co-founder and CEO of Clearmotive Marketing, a Calgary-based agency he has led for over 15 years. He is the author of Curious as Hell: Leading & Growing with Curiosity, and host of more than 650 podcast episodes across Collisions YYC and They Just Get It. Tyler speaks regularly on curiosity as a leadership skill and is also the founder of Red Express, a holiday initiative that delivers toys to children in need.

Key Takeaways:

• The myth of the all-knowing leader is doing real damage. Most corporate structures still echo a Roman military command-and-control model — which made sense in war zones and makes a lot less sense in boardrooms.
• Curiosity has three tiers, and they go in order: self-curiosity, relational curiosity, and strategic curiosity. Skip the first two and the third one fails under pressure.
• Self-curiosity is the work of catching yourself before you jump in. How am I getting triggered? Am I creating space, or filling it?
• Relational curiosity is built before the pressure hits — knowing your team well enough that trust holds when things get uncomfortable.
• Strategic curiosity is what every founder wants in the room: people asking what we are not seeing, what if we flipped this, what is the unexamined assumption. It only works if the first two tiers are intact.
• Saying I don't know takes courage. In environments built around the appearance of certainty, that small admission is one of the most leadership-grade things a person can do.
• Teams read every micro-signal. Whether ideas get supported or shut down, whether questions are welcomed or rushed past — every one of those moments writes the operating system for how things go around here.
• A pen-and-paper habit changed Tyler's leadership. After every meeting, he wrote which side of the line his behaviour landed on: fixed mindset or growth mindset. Six weeks of that quiet observation changed the way he led.
• Curiosity is also a defence. When the world rewards reaction over reflection, a deliberate pause becomes a kind of armour against being manipulated.
• Bravery gets you through the door. Curiosity figures out what to do once you are inside.

Connect With Tyler Chisholm:

• 🌐 Website: https://www.tylerchisholm.com
• 💼 LinkedIn: https://www.linkedin.com/in/tylerchisholm/
• 📘 Book — Curious as Hell: Leading & Growing with Curiosity: https://www.amazon.com/Curious-As-Hell-Leading-Curiosity/dp/1069373729
• 🎙️ Podcasts: Collisions YYC and They Just Get It (find via Tyler's website)
• 📰 Newsletter and resource library: https://www.tylerchisholm.com

A Quick Note Before the Episode Begins:

You will hear a few seconds of pre-show conversation before the episode formally begins. Tyler, a podcaster himself, shares a quiet appreciation for the medium and what it makes possible — meaningful, deliberate, deeply personal conversations. We have left it in because it sets the tone for everything that follows.

Episode Chapters:

[00:00] The Myth of the All-Knowing Leader — Why this is the wrong playbook

[03:00] The Pool Cue Story — How a teenage moment of honesty seeded a leadership philosophy

[06:00] Why "I Don't Know" Takes Courage — The legacy of command-and-control

[10:00] What It Looks Like in Real Life — The three tiers of curiosity

[14:00] Reading the Room — How teams quietly learn what is and is not allowed

[18:00] Curiosity as a Life Skill — Inside the boardroom and outside it

[20:00] The Pen-and-Paper Experiment — Six weeks that changed Tyler's leadership

[23:00] Curiosity as Defence — When reflection becomes armour

(Timestamps approximate)

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