Curious as Hell – Détails, épisodes et analyse

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Curious as Hell

Tyler Chisholm

Business & Entrepreneuriat

Éducation

Fréquence : 1 épisode/0j. Total Éps: 7

The podcast where relentless curiosity meets leadership transformation. Hosted by Tyler Chisholm—entrepreneur, CEO, and lifelong learner—Curious as Hell is the go-to podcast for leaders, innovators, and trailblazers who believe that asking the right questions can unlock new possibilities in business and life. In each episode, Tyler sits down with top executives, entrepreneurs, and thought leaders to explore how curiosity fuels innovation, builds stronger teams, and drives personal growth. Whether it's uncovering the leadership strategies behind top-performing companies, unpacking the mindset shifts that foster resilience, or challenging conventional wisdom, Curious as Hell delivers actionable insights that help you lead with confidence and creativity. If you're a growth-minded leader looking for fresh perspectives, practical strategies, and inspiring conversations that push boundaries, then you're in the right place.

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🇨🇦 Canada - management
19/06/2026
#100
🇨🇦 Canada - management
18/06/2026
#60
🇨🇦 Canada - management
12/06/2026
#60
🇨🇦 Canada - management
11/06/2026
#84

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Liens partagés entre épisodes et podcasts

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https://tyler-chisholm.kit.com/products/curious-as-hell-support-the-newsletter
7 partages
http://clearmotive.ca/?utm_source=podcast&amp
4 partages
http://www.platformcalgary.com?utm_source=podcast&amp
1 partage

https://www.linkedin.com/in/jayson-krause/
1 partage
https://www.linkedin.com/in/iggydomagalski/
1 partage
https://www.linkedin.com/in/bobbiejoracette/
1 partage

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Curious as Hell S01E01: Your Team Stopped Telling You The Truth. Here's Why.

Épisode 1

lundi 8 juin 2026 • Durée 56:50

A leader who thinks they have all the answers is not leading. They are performing certainty, and that performance has a price.

Tyler Chisholm is the founder of clearmotive, the author of *Curious as Hell: Leading and Growing with Curiosity*, and the host of this new podcast series. In this first episode, fellow podcaster and former journalist Leah Sarich turns the mic on Tyler to surface the origin story behind the book, the philosophy behind the show, and the very specific, very costly moments that convinced him certainty is the real risk in leadership.

What emerges is a candid account of how a leader who once believed he had all the answers learned, painfully and more than once, what that certainty actually cost. Tyler walks through the pool cue story from when he was 19, the failed business sale from his early 30s, the fixed vs. growth scorecard he built during COVID, and the results he has seen at clearmotive, including a significant increase in profit margin with 10 fewer full-time staff.

Key themes from this episode:

Why certainty, not ignorance, is the most dangerous thing a leader can carry into a room. The distinction is uncomfortable, but Tyler makes it plainly: you can be uncertain about something you know nothing about, or you can be certain about something you have misunderstood completely, and the second one is the one that will cost you.

What the leadership 360 actually revealed, and why the feedback "Tyler, you're showing up asking questions you already know the answer to" landed harder than any performance review. The gap between performing curiosity and practising it is where most leaders quietly live.

How the facts vs. feelings framework cuts through the noise in difficult meetings. When Tyler walks through this exercise, the point becomes clear: most of what leaders call a problem is actually a feeling they have not yet examined.

What psychological safety actually means in practice. Not a feelings discussion. Not a culture initiative. The freedom to dissent, and the moment-by-moment test of how a leader treats the person who uses it.

Why self-curiosity is the only legitimate starting point, and what it looks like to build it through low-tech, deliberate practice.

How Microsoft's transformation under Satya Nadella illustrates the business case for curious leadership at scale, from billion-dollar to trillion-dollar company.

Chapters:

0:00 — Introduction

2:37 — How podcasting opened the door to curiosity

7:28 — The risk of certainty: season 1 theme

10:45 — The rutabaga: what is on the book cover and why

15:33 — The pool cue story: an early lesson in not pretending

18:53 — When certainty cost everything: the failed business sale

21:16 — The fixed vs. growth scorecard

23:36 — Why the current leadership model is breaking down

26:47 — Curiosity as a cure for leader burnout

29:07 — What curiosity looks like on a Wednesday

33:27 — Listening as the engine of curiosity

38:55 — Psychological safety: the freedom to dissent

47:00 — Curiosity checkpoints

47:24 — Real results at clearmotive

52:37 — The Microsoft story

52:52 — What Tyler hopes leaders take away

54:24 — What to expect from Curious as Hell

Connect with Leah Sarich

Learn more about clearmotive

If this conversation was useful, subscribe wherever you listen and leave a review. It helps more leaders find the show.

★ Support this podcast ★

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Curious as Hell S01E04: She Walked Away from a Merger After Two Years. Then Became CEO of a Pro Sports Team.

Épisode 4

lundi 8 juin 2026 • Durée 58:11

In 2021, Canada won Olympic gold in women’s soccer. Yet the country still did not have a

professional league. At the 2023 FIFA World Cup, Haiti and Canada were the only countries

without female domestic leagues. But Canada finally has one. The Northern Super League had

its first season last year, in 2025. Lara Murphy is the co-founder, president, and CEO of the

Calgary Wild FC, one of the league’s founding teams, and she is dedicated to helping build this

team and this new league.

Before that, Murphy co-founded Ryan Murphy Construction, becoming one of the few women to own a commercial construction company in Canada. She is still running her company 18 years later, in addition to her role in professional soccer.

Murphy started out as a soccer player. She was recruited out of New Brunswick at age 17 and

played in England, long before a professional path existed for women in this country.

This conversation covers what happens when purpose collides with the realities of building a

business, how you hand off the company you built from scratch, and why the hardest leadership

skill is not strategy or vision, but patience.

Key themes from this episode:

Lara Murphy on what it takes to be first: being the first pro women’s team in Alberta means there is no one ahead of you to learn from, no template, and no forgiveness for the same mistake twice.
The identity trap of the early-stage founder: most of us get rewarded early in our careers for how many bricks we can pile, and the shift to leading the people who pile bricks is harder than it sounds.

Curious as Hell S01E02: The Leadership Lessons I Didn't Learn Until 3,000 Employees

Épisode 2

lundi 8 juin 2026 • Durée 01:07:23

When a senior leader retires, their phone stops ringing. Almost immediately. Iggy Domagalski noticed this and built his entire personal mentorship network around it. He maintains relationships with between 10 and 15 mentors and connects with each of them every six months with a written list of questions. The group most willing to give their time was available and brought value to every single conversation.

That is one idea from this conversation. The rest is equally powerful.

Iggy was part of the team that acquired Tundra Process Solutions in 2006 and scaled it to 150 people before its acquisition, then spent four years as CEO of Wajax, one of Canada's oldest companies at 168 years old. He came in as an outsider, visited 80 of the company's 100-plus branches in his first three months, and spent the next four years learning what actually happens when you try to shift the leadership culture of a 168-year-old organization.

Not everything landed the way he intended. He is honest enough to say exactly what he would do differently.

Key themes from this episode:

On the hubris of the early leader: "I just had some opinions on things, the way I thought that things should be done based on not very good information or experience." That line from Iggy is worth sitting with.
On the recently retired mentor sweet spot: when someone exits a senior role, their phone stops ringing almost overnight. If you are the one calling, you have their full attention and the benefit of everything they learned.
On culture change and unintended consequences: a leadership initiative meant to strengthen culture started to erode the performance expectations beneath it as the language spread deeper into the organization. Iggy walked it back deliberately and explained how.
On making decisions without perfect information: "We don't have all the information here, but this is good enough. This is what we're doing. And when we walk out of here, we need everyone aligned and singing from the song sheet."
On the think day: Iggy has been scheduling deliberate, phone-off, handwritten thinking sessions at a coffee shop for years. Every single time, he left telling himself it was the best use of his time. Every single time, the urgency of the week pulled him back.

Curious as Hell S01E06: She Led as CEO for 6 Months Without Knowing If She'd Get It

Épisode 6

lundi 8 juin 2026 • Durée 01:10:45

The habits that made you an exceptional doer are the same ones quietly working against your team now.

Jennifer Lussier spent six years raising her hand for every available role at Platform Calgary, moving from contract advisor to COO after her tech startup failed in 2019. She ran the organization as interim CEO for six months while simultaneously competing in a formal three-interview search to make the role permanent, and was elected CEO two months before this conversation was recorded.

This episode goes directly into what actually changes when the title changes, and why most of that change is subtraction.

KEY THEMES FROM THIS EPISODE

Making everybody a leader: Jennifer is building a culture at Platform where every team member, from VP to the person at the cafe counter, operates with a shared set of fundamentals: agency, resilience, adaptability, and mentorship. The goal is an organization where people make values-aligned decisions without waiting for direction from above.
High stakes vs. low stakes: One of the most expensive habits in leadership is reading every situation as critical. Jennifer trained herself to ask the actual size of the risk before responding, and describes how reframing a media appearance as just answering a question to another human changed her performance under pressure.
Transparent leadership with calibration: Jennifer leads with openness, including sharing the uncertainty of her own interim process with her team in real time. But she draws a deliberate line: shoulder the scary parts, communicate the known.
Naming your bias before the meeting: When Jennifer has a gut read on a decision, she states it before the discussion starts. Here is my bias. Call it out. It removes the dynamic where the team performs agreement because the leader has already landed somewhere.
The COO-to-CEO shift: The operational instinct to solve, fix, and stay in the details does not disappear when the title changes. Jennifer describes the deliberate work of pulling out of people’s business to focus on what only the CEO can do: build better leaders and look further down the road.
Career trees: Platform is building multi-path career development internally, where team members can move across functions with an internal mentor guiding the transition. The goal is to send people out more capable than they arrived, even if that means losing them.

Curious as Hell S01E07: Retain Better. Burn Out Less. Build Teams That Don't Need You in Every Room.

Épisode 7

lundi 8 juin 2026 • Durée 01:56:20

Season one of Curious as Hell asked one question: What does it really mean to lead today? Over six conversations, a pattern kept emerging. The leaders who were doing it well weren't the most credentialed or the most certain. They were the ones who had stopped pretending they had all the answers.

In this final episode of Season 1, Tyler is joined by Meghan, a PhD in Industrial/Organizational Psychology and the founder of Pebble, who steps in as co-host to help unpack what the season's guests were really saying. Together they work through three themes: Curiosity, Not Expertise; Relational and Co-Created; and Growth Through Reflection.

Part 1: Curiosity, Not Expertise

The guests who led best had learned, sometimes painfully, to stop leading from what they knew and start leading from what they were willing to find out. Tyler shares the 360 feedback that first cracked open his own leadership. Bobbie Racette talks about the tunnel vision of a startup founder who was moving one direction while the business quietly went another. Iggy Domagalski looks back at the opinions he confused for facts. Lara Murphy unpacks the real difference between asking for help and just delegating work.

Meghan brings the research lens: why do leaders cling to expertise even when it is clearly not working? Part of it is identity. When you got promoted because you were the best at something, letting go of that thing can feel like letting go of the reason you are in the room. What you have instead of expertise, she argues, is the people around you. That is the resource.

Part 2: Relational and Co-Created

Jennifer Lussier's team made "Vote for Jen" stickers when she was interviewing for the CEO role she had been filling as interim. That story, Tyler says, does not require an engagement survey to interpret. Meghan builds on it: the research keeps pointing to the same thing, that the relationship with your manager is the primary driver of whether someone stays, contributes, or quietly leaves. Jayson Krause calls it relational equity and argues that most organizations are measuring the wrong thing entirely.

Curious as Hell S01E05: The Leader With the Fewest Blind Spots Wins. Not the Smartest. Here's Why.

Épisode 5

lundi 8 juin 2026 • Durée 01:12:46

The skills that got you promoted are the same ones quietly strangling your team's potential.

Jayson Krause spent eight years as a funded national team bobsled athlete before discovering that the most important performance arena is not a track. It is the room where a senior leader decides whether to solve a problem or ask a question. Since 2010, he has worked with CEOs, founders, and senior executives across Canada and the US, and his message is consistent: curiosity is not a soft skill. It is an operational discipline with a measurable ROI.

This conversation goes directly at the habits, reward systems, and hidden costs that keep smart leaders stuck, and the framework for getting unstuck.

Key themes from this episode:

The three triggers that bring leaders to coaching: the board mandate, the proactive edge-seeker, and the nightmare that wakes you up at 2 am. Mandated coaching rarely works. Pain is what actually creates space for real change.
The Awareness, Intention, Experiment, Reflection (A-I-E-R) model: how to move from reaction to reflection before you blow it, borrowed from elite sport and applied directly to leadership behaviour.
The seduction of solving: every time you answer a question your team could have answered themselves, you get a dopamine hit and they lose a development opportunity. The habit is well-intentioned and quietly destructive.
Relational equity: your engagement problem is not a culture problem. It is a measurement problem. Jayson explains what to track instead.
The meerkat story: a COO described by his team as the Grim Reaper rebuilt his entire reputation in six months through deliberate, specific work. This is what that actually looks like.
What happens when you ask your team "What would make this the best year of your professional career?" and actually wait for the answer: most leaders have never asked it. Most teams have never been asked.

Chapters:

0:00 — Introduction
1:29 — Jayson's path: from national team athlete to executive coach
3:57 — Coaching without having been there: the asset nobody talks about

Curious as Hell S01E03: No Grade 11. 170 Investor No's. The Decisions That Built the Company

Épisode 3

lundi 8 juin 2026 • Durée 59:59

Nobody would hire her. So she listed herself on Kijiji for $22/hour and built a company from that. Nine years later, she was signing exit papers, and she could not tell a single person it was happening, not even her wife. This is the version of that story she could not tell while it was happening.

Bobbie Racette founded Virtual Gurus in 2016 after being turned down for every job she applied for as a queer, Indigenous woman in tech. She built it from a Kijiji posting with no grade 11 education and no playbook, through 170 investor rejections, into a VC-backed company she exited nine years later. She is now the chair of Queer Tech and the Indigenous Prosperity Foundation, and is building Tapwi, a FinTech platform for underserved founders named after the Cree word for truth.

This conversation does not tell the version of the story that looks good on LinkedIn. It goes into the cost of hiding your identity, the people-pleasing trap that stalls real growth, and what it actually takes to process an exit when you cannot talk about it with anyone.

Key themes from this episode:

On the risk of certainty: Bobbie admits she was so fixed on where the business was going that she almost missed where it was actually heading. Certainty without curiosity nearly cost her the company.
The moment she stopped hiding: A young trans woman showed up at her three-person office after hearing Bobbie on the radio and said she had saved her life. That was the day Bobbie decided to tell her story fully, every time, and everything changed.
Building a culture around story: The employees who joined in the final three years of Virtual Gurus were not there for the paycheck. They were there because they had a story, and they felt it was the place where their story would be accepted.
The people-pleasing trap: "I tried to make everybody happy versus understand the risks that needed to go. And I think that's where mistakes happen." It was not until Bobbie stopped trying to bring everyone along that the real growth started.
Choosing to learn from the exit: She blamed the board, she blamed the new CEO, and then she chose differently. "I could choose to learn, or I could choose to really hate this. And I chose to learn from it."

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