What can improv comedy teach us about leadership?

More than you might think.

In this episode James H Stewart sits down with Simon Dowling, whose career has taken an unusual path through commercial law, executive education, leadership — and improv comedy.

Simon began his professional career as a commercial lawyer with Gadens before moving into executive education, negotiation and communication. At the same time, he spent around 16 years as an ensemble performer in improvisational comedy, including with Impro Melbourne and on Working Dog Productions’ hit television show Thank God You’re Here.

Today, Simon works with CEOs and leadership teams on trust, communication, collaboration and building more effective teams. He is also the author of Work With Me: How to Get People to Buy Into Your Ideas.

In this conversation, James and Simon explore what the principles of improv can teach business leaders about listening, trust, adaptability and performing under pressure.

They also discuss:

• Why leadership teams become dysfunctional

• The respective roles of leadership, team composition and culture

• How leaders build trust — and earn it from their teams

• The difference between leadership and getting genuine buy-in

• When collaboration becomes counterproductive and leaders simply need to make a decision

• Simon's concepts of focus, flow and care in effective teams

• The lost art of conversation and the importance of genuinely listening

• Managing emotion when leadership gets difficult

• The mistakes Simon sees CEOs repeatedly make

• What Simon believes about leadership today that he didn't believe 20 years ago

It's a conversation about what happens when leadership theory meets human behaviour — and what a career spent performing without a script can teach you about leading when things don't go according to plan.

DISCLAIMER: What I Learned in Business (That Didn’t Kill Me!) is produced for general information and entertainment purposes only. The views, opinions and experiences expressed by guests are their own and do not necessarily represent those of James H Stewart, the podcast, or any organisation with which either the host or guest is associated. Nothing in this episode constitutes legal, financial, investment, business or other professional advice and should not be relied upon as such. References to individuals, companies or organisations are made in the context of the discussion. Listeners should make their own enquiries and obtain appropriate professional advice before acting on any information discussed in this episode.

Hosted on Acast. See acast.com/privacy for more information.

Jamie Whincup is one of the most successful drivers in Australian motorsport history — a seven-time Supercars champion, four-time Bathurst 1000 winner and winner of 125 Supercars races. But his journey to the top was anything but straightforward.

Jamie joins James H Stewart to talk about starting out in karting, winning the Australian Formula Ford Championship at just 19, being hired — and then fired — by Garry Rogers Motorsport at 20, and fighting his way back into professional racing.

He shares the story of joining Triple Eight Race Engineering, racing alongside Craig Lowndes, winning three consecutive Bathurst 1000s together and building one of the most successful careers in Australian motorsport.

But this conversation isn't just about racing.

Jamie discusses becoming a shareholder in Triple Eight, what he learned from Roland Dane and some of the successful businesspeople around the team, and the very different challenge of retiring from full-time racing and becoming Triple Eight's Managing Director and Team Principal.

We explore the economics of running a professional racing team, the role of data versus instinct, managing elite performers, transitioning from individual competitor to business leader, and Triple Eight's major decision to move from GM to Ford in 2026.

It's a conversation about resilience, competition, leadership and what happens when your job changes from winning yourself to creating an organisation

capable of winning without you.

Disclaimer: This podcast is provided for general information and entertainment purposes only. The views and opinions expressed by guests are their own and do not necessarily reflect those of James H Stewart, What I Learned in Business (That Didn’t Kill Me!), or any associated organisation. Nothing discussed in this episode should be regarded as financial, investment, legal or other professional advice. Listeners should make their own enquiries and seek appropriate professional advice before making decisions based on matters discussed in the episode.

Hosted on Acast. See acast.com/privacy for more information.

What can almost 30 years with the elite SAS teach business about leadership, resilience and building teams that perform?

In this episode James H Stewart sits down with Harry Moffitt—former SAS soldier, registered psychologist, author and founder and CEO of the Stotan Group.

Across 11 operational deployments, Harry spent close to 1,000 days on Special Operations missions. He was seriously wounded in Afghanistan in 2008 and later became the SAS Human Performance Manager, bringing together his operational experience and study of psychology to better understand what enables people and teams to perform under extreme pressure.

Harry and James explore the lessons from that extraordinary career and, importantly, how they translate into business. They discuss leadership and decision-making under pressure, resilience and mental health, the importance of trust in elite teams, whether character matters more than talent, what business leaders misunderstand about high performance, and how leaders should respond when organisations find themselves in crisis.

Harry also discusses his love of cricket and his first book, Eleven Bats, as well as his latest book, The Fourth Pillar, which explores why physical, psychological and social wellbeing may not be enough—and why having a philosophical foundation can be critical to living and leading well.

It’s a fascinating conversation about character, purpose and what it really takes to perform when things get difficult.

In this episode:

• Leadership lessons from almost 30 years in the military including 11 deployments with the SAS

• Recovering after being seriously wounded in Afghanistan

• Making decisions when the consequences really matter

• Resilience, psychology and mental health

• Why trust is fundamental to high-performing teams

• Character versus talent

• Stoicism and its relevance to modern leadership

• What Special Forces can—and can't—teach business leaders

• Leading organisations through crisis

• Eleven Bats and the unlikely connection between cricket and combat

• The Fourth Pillar and the importance of purpose and philosophy

What I Learned in Business (That Didn't Kill Me!) explores the lessons learned through success, failure and everything in between.

Disclaimer: The views and opinions expressed in this podcast are those of the host and guest in their personal capacities and do not necessarily represent the views of any current or former employer, organisation, government agency or other entity with which they have been associated. The discussion is provided for general information and entertainment purposes only and should not be relied upon as professional, psychological, medical, financial or other advice.

Hosted on Acast. See acast.com/privacy for more information.