There is nothing quite like a weekend drive to Central Otago for skiing to clear your head. The open landscapes, fresh air and a great music or podcast that makes it even better. And since we travelled a few times last month, there was plenty of time to learn and discover some interesting content. I’ve chosen three of my favourite podcasts with a leadership theme to feature here.
If you are driving somewhere fun or commuting to work, strap in, hit play, and enjoy the ride.

The Knowledge Project: Harley Finkenstein (Shopify)

In The Knowledge Project episode titled “Harley Finkelstein: You Must Requalify for Your Role, Every Year,” Shopify President Harley Finkelstein opens up about the mentors who have shaped his journey, which he calls his personal Board of Directors. Seth Godin’s mentorship was particularly instrumental, helping Harley transition from a COO role and explore the power of storytelling as it relates to business strategy and quarterly results. As Harley says,

“Earnings calls are a storytelling opportunity, not just a technical report. Leadership today is about narrative, not selling widgets.”

He also explores the deeply personal journey of navigating his ego, the drive to feel important, and the conversations with Shopify CEO Tobi Lütke, who consistently saw a better version of Harley than he saw in himself. Harley credits Tobi as a mentor who pushed him to grow and continuously “requalify” for his role.

Finkelstein also critiques the industry’s superficial embrace of AI, noting that simply mentioning it without genuine integration is like putting up a sign instead instead of building a true culture. As he puts it:

“A lot of companies are very hand-wavy about AI. It’s like putting up a sign that says, ‘We’re doing AI now,’ but it’s not a culture. It’s not a real change.”

Leadership Horizons with Lois Burton

In the Leadership Horizons episode “The Courage to Change Course,” executive coach Lois Burton explores when and why leaders should pivot. She highlights the tension between staying committed and adapting to change and new directions. Burton identifies five signals that a change in direction is necessary: shifting assumptions, critical staff or customer feedback, rising costs of staying the course, team distress, and better alternatives.

“Sometimes the strongest thing a leader can do is admit they were wrong – fully owning that decision and the ‘why’.”

She outlines a framework for executing change effectively: own the decision, communicate the “why,” honor past investments, and generate enthusiasm for the new direction. Burton concludes that the strongest leaders are those who repeatedly choose the right course as circumstances evolve.

Between two Beers: Zion Armstrong

Wow, what a journey. Zion Armstrong’s story begins in the streets of West Auckland, where as a teenager he was running from the police. That moment could have defined his life but instead, it became a turning point. It led him to discover his talent as a runner, eventually competing in the Commonwealth Games and setting him on a path that would take him from athletics to the board rooms of Adidas. He talks about the power of being intentional along the way:

“Too busy getting there to know where you are going… book yourself two or three blocks a week to meet with yourself. If you don’t do that, life just happens to you.”

During his tenure as President of Adidas North America, Zion Armstrong recognized the influence Black and Latino communities had on sneaker culture. He didn’t just see them as ‘consumers’, he recognised that they were also the cultural architects behind the trends that drove the industry – and with his leadership Adidas was able to translate these consumer insights and passion into great products that ultimately drove the revenue growth of the brand at the time.