The best interviewers are the ones who make you forget you are being interviewed.
That is exactly what Tyler Chisholm did to me the first time we recorded together. Then he did it again the second time when he interviewed me years later. In both cases, within 10 minutes I felt like I had known him forever.
This is Chisholm’s gift. He has a remarkable ability to make someone feel welcome, listened to, and understood.
Now more than 5 years after launching the CollisionsYYC podcast, Chisholm is celebrating two milestones.
He recently released the 500th episode of the podcast and published his first book, Curious as Hell: Leading & Growing with Curiosity. Both reflect the philosophy that has guided his work from the beginning: curiosity is not a personality trait, it is something you practise and strengthen over time.
To mark the milestone, Chisholm hosted a live event at Calgary’s TELUS Convention Centre this week, drawing more than 200 people from across the city. The evening featured panel discussions with leaders from Calgary’s innovation and business communities, and ticket proceeds supported the Calgary Food Bank.
As someone who interviews others for a living, I know how hard it is to make people feel at ease quickly. Chisholm’s style is thoughtful, calm and focused on the guest. He listens closely and builds conversations that feel both personal and broadly relevant.
This milestone is the result of years of deliberate practice in hosting, storytelling and showing up with curiosity. It reflects Tyler’s rare ability to make people feel understood, and his commitment to building trust through conversation has created a platform that brings out the best in others.
A podcast rooted in curiosity
CollisionsYYC began as a personal experiment. Chisholm, who is also the CEO of a marketing and customer experience agency called clearmotive, was looking for a new creative outlet and knew he preferred conversation over writing.
“I don’t really like writing. I like talking. Maybe a podcast would be a thing,” he said. “It was very innocent, very naive.”
Chisholm recorded his first few episodes with people he knew — or thought he knew. But as the mics went on and the conversations unfolded, something shifted. The interviews revealed layers of their experiences that he hadn’t seen before.
“At the end of the hour, I walked away thinking: Holy shit, I didn’t know anything about them before. I really didn’t know their story, or their journey,” he said.
Chisholm realized the format was doing something powerful for his ability to connect with people, learning that good podcasting isn’t just content but opening up deeper, more honest conversations.
“I fell in love with what I got to take away from it,” he said.
That shift pushed him to dive into the format and focus on his skills as an interviewer. Instead of making himself the centre of the show, he deliberatly focused on making each guest the main character.
“I wanted to make them the hero,” he said, “and think about their role and their world and how I was going to share that story.”
The idea to start the podcast came after a conversation with Kevin Crowe, now Chief Operating Officer of Long View Systems. Crowe had pointed out that people solving problems and people experiencing those problems were often living on opposite sides of the street and not talking to each other. He urged Chisholm to do something about it.
Chisholm suggested Crowe start a podcast.
Crowe pushed back and told him, “No. You should start the podcast.”
That was in 2019, as Calgary was still navigating a years-long energy sector downturn. Chisholm began to use the show to surface stories of innovation, ambition and problem-solving from across the city.
“There were positive things happening,” he said. “I really wanted to latch onto that.”
When the COVID-19 pandemic hit, the show evolved again. Guests were easier to reach, and the shift to remote interviews made it easier to record consistently.
“It quickly became business networking on steroids,” he said.
As the guest list expanded, so did Chisholm’s understanding of what the show could be.
“I’ve had 500 mini MBAs, and I would do this podcast even if nobody listened because of the benefit I got from those interviews.”
A style shaped by structure and instinct
Although each episode feels relaxed, Chisholm applies a deliberate structure behind the scenes. He often builds interviews around the arc of the hero’s journey, using narrative techniques to guide listeners through a beginning, challenge and resolution.
“The little chess game I get to play is, how can I turn this person into that narrative so the audience can enjoy the journey?” he said.
What makes the format work is how quickly Chisholm makes guests feel comfortable (as was the case in my experiences). He says the first few minutes of an interview can determine whether someone opens up or holds back.
“There’s a direct correlation between how comfortable you are and how comfortable the guest is,” he said. “I’ve had many people say, ‘Five minutes in, I forgot I was even on the show.’”
Early feedback from listeners also helped shape his approach and over time, he fine-tuned how much to paraphrase, how to prompt without interrupting, and how to add to a conversation without overshadowing it.
“The right amount of paraphrasing, the right amount of pulling, the right amount of adding to build, not to take over the conversation,” he said. “It’s not about you. It’s about the guest.”
The longer he hosted, the more Chisholm noticed curiosity changing the way he led his business and interacted with others. The habits he built behind the mic began to show up in meetings, in team conversations and in how he processed challenges. He started to see curiosity not as a tool for content, but as a foundation for leadership.
That insight became the basis for his book.
Curious as Hell outlines three key areas of curiosity: toward yourself, toward others and toward the world around you. The book is written for people stepping into leadership roles and looking for an approach that values openness, reflection and trust over control.Chisholm says it’s the kind of book he wishes he had read when he was 35.
He also describes curiosity as a practice — something you have to work at, not something you either have or don’t.
“This is not a ‘got it, figured it out’ thing. This is a journey.”
Chisholm also wrote the book because he believes generational expectations have shifted and command-and-control leadership styles no longer work for younger team members who value transparency and shared purpose.
“If you’re in your 50s and not thinking about this, good luck getting younger members of your team to follow you,” he said.
A record of voices and transformation
Over the course of 500 episodes, CollisionsYYC has grown into a long-form record of Calgary’s innovation ecosystem. Guests have included founders, policymakers, researchers and community leaders. Some episodes have captured early-stage conversations about major shifts in industry, talent and technology.
Chisholm said he never planned to tell the story of the city. He simply kept showing up, asking questions and making space for people to speak.
In addition to CollisionsYYC, he hosts a second podcast called They Just Get It, which features people who have taken unconventional paths through work and life. The book adds a new layer to his work, capturing what he has learned along the way and offering it back to others.
What ties it all together is a consistent philosophy: conversations matter, especially when they are grounded in trust. And if we are willing to listen with intention, we may learn more than we expect.
Chisholm has helped people across Calgary tell their stories in their own words. He has treated each guest as someone worth learning from. And in doing so, CollisionsYYC serves as a reminder that careful, consistent listening is still one of the most powerful tools we have.
You can listen back through Tyler’s 500 episodes at the Collisions YYC website here.
This article was created with the assistance of AI. Learn more about our AI ethics policy here.
