The Surprising Power of Humility at Work | Simon Moss

05/13/25 • 66 min

When we talk about what makes a great leader, we tend to focus on confidence, decisiveness, and maybe even charisma. Less often do we talk about humility. And yet, humility, according to psychologist Dr. Simon Moss, may be the trait that unlocks the most growth, resilience, collaboration, and trust. In this episode, Dart and Simon talk about why humility isn’t the opposite of confidence, how future clarity increases self-awareness, and how organizations can be structured to reward groundedness instead of ego.
Dr. Simon Moss is a psychologist and Dean of Graduate Research at the University of Wollongong. His research focuses on workplace behavior, ethical leadership, and the psychological conditions that promote wellbeing, performance, and integrity at work.
In this episode, Dart and Simon discuss:

- The difference between humility and insecurity
- Why humble leaders often drive stronger performance
- How clarity about the future shapes grounded leadership
- The cultural conditions that reward narcissism
- The relationship between time pressure and defensiveness
- How to design humility into hiring, leadership, and culture
- The mission of Radical Humility
- And other topics...
Dr. Simon Moss is a registered psychologist and the Dean of Graduate Research at the University of Wollongong. His research focuses on how organizational and government policies impact individual wellbeing, progress, and innovation. He has authored approximately 10 books and over 100 peer-reviewed papers, with a focus on workplace behavior, ethical leadership, and emotional intelligence.
Simon is the founder of Radical Humility, a research initiative aimed at reducing narcissism in leadership and helping organizations cultivate grounded, human-centered cultures. His books include The Negative Side of Positive Thinking, Where Should I Work? and Emotional Intelligence: Journey to the Source.
Resources Mentioned:
Radical Humility: https://radical-humility.comConnect with Simon:
LinkedIn: https://www.linkedin.com/in/simon-moss-5334944/
Email: [email protected]

Work with Dart:
Dart is the CEO and co-founder of the work design firm 11fold. Build work that makes employees feel alive, connected to their work, and focused on what’s most important to the business. Book a call at 11fold.com.

Previous Episode

Listening Beyond Words: How to Really Hear People at Work | Oscar Trimboli

Oscar Trimboli has spent his life helping people hear what’s not being said. As a listening expert and advisor to some of the world’s largest companies, he’s discovered a surprising truth: most of us only catch a fraction of what’s being communicated. We hear the words, but miss the silences, emotion, and meaning beneath them. In this episode, Dart and Oscar explore the five levels of listening, what it takes to make someone feel truly seen, and how listening can be taught, measured, and embedded into teams.
Oscar Trimboli is a speaker, leadership coach, and the author of How to Listen. He hosts the Apple award-winning podcast Deep Listening and has worked with clients such as Microsoft, AstraZeneca, and Cisco to improve communication and collaboration through listening.
In this episode, Dart and Oscar discuss:
- The five levels of listening
- What it takes to make someone feel truly seen at work
- Why most of us only hear 14% of what someone really means
- The link between listening and action
- How listening can reduce meetings and increase effectiveness
- Why silence is the most powerful listening tool
- What metaphors reveal about how people see the world
- How to teach listening as a core leadership skill
- And other topics...
Oscar Trimboli is a speaker, author, and host of the Deep Listening podcast. His mission is to create 100 million deep listeners in the workplace. He’s advised organizations including Microsoft, AstraZeneca, and HSBC on how to listen beyond the words and build cultures of understanding. His latest book, How to Listen, explores the science and practice of listening well—and why most of us do far less of it than we think.
Resources Mentioned:
How to Listen, by Oscar Trimboli: https://www.amazon.com/How-Listen-Discover-Hidden-Communication/dp/1774581914
The Deep Listening Podcast: https://www.oscartrimboli.com/podcast/
Listening Quiz (Discover your listening barriers): https://www.listeningquiz.com
Unreasonable Hospitality, by Will Guidara: https://www.amazon.com/Unreasonable-Hospitality-author/dp/1529146828
Don't Think of an Elephant! by George Lakoff, Howard Dean, & Don Hazen: https://www.amazon.com/Dont-Think-Elephant-Values-Politics/dp/1931498717
Connect with Oscar:
Website: https://www.oscartrimboli.com
LinkedIn: https://www.linkedin.com/in/oscartrimboli

Next Episode

Built on Audacity: How to Be Bold at Work and Take Worth-It Risks | Anne Marie Anderson

At its best, work is co-created. It’s not something companies hand out—it’s something employees help build by showing up fully and taking risks. But that kind of courage requires something we don’t talk about enough: audacity. Anne Marie Anderson has built her career on it. She’s worked in 82 countries, broken ground as one of ESPN’s first female sideline reporters, and navigated some of the most high-stakes environments in sports broadcasting. For Anne, audacity isn’t about fearlessness—it’s about dismantling doubt, trusting your voice, and building the kind of support system that helps you leap anyway.
In this episode, Anne and Dart talk about what makes someone bold enough to raise their hand, speak up, or swing big, even when failure is possible. They explore the four barriers to audacity, the difference between recklessness and worth-it risk, and how to build the kind of support system that helps people take meaningful leaps at work.
Anne Marie Anderson is a keynote speaker, leadership coach, and former sports broadcaster who has worked with ESPN, CBS, and NBC. She’s the author of Cultivating Audacity, and helps individuals and teams unlock courageous performance through mindset, resilience, and presence.
In this episode, Dart and Anne discuss:
- The four barriers that hold people back from bold action
- The difference between recklessness and worth-it risk
- How to turn rejection into resilience
- Why boldness is a habit, not a personality trait
- The “front row” mindset and how to build one
- The connection between belonging and courage
- Lessons from high-pressure moments in sports and broadcasting
- And other topics...
Anne Marie Anderson is a keynote speaker, leadership coach, and former ESPN broadcaster. She’s the author of Cultivating Audacity: Dismantle Doubt and Let Yourself Win. Anne helps individuals and teams build confidence, take bold risks, and lead with authenticity. Through her 25+ year career in sports media and performance coaching, she has worked in over 80 countries and brings deep experience in high-stakes communication and personal growth.
Resources Mentioned:
Cultivating Audacity, by Anne Marie Anderson: https://cultivatingaudacity.com
Limitless, by Laura Gassner Otting: https://www.amazon.com/Limitless-Ignore-Everybody-Carve-your/dp/1940858763
Connect with Anne:
LinkedIn: https://www.linkedin.com/in/anne-marie-anderson-3557ab39/
Instagram: https://www.instagram.com/annemarieandersontv/
Website: https://annemarieanderson.com