Connecting to Admired Leadership
The Humility Myth
Episode Summary
A conversation with Admired Leadership Coach & Partner Ben Stringfellow and Wes Bender from CRA | Admired Leadership, exploring why the popular understanding of humility is fundamentally wrong - and why getting it right is one of the most powerful things a leader can do. Opening with a story of a fraternity president candidate who declared himself "easily one of the most humble people I know," this session reframes humility not as withdrawal or self-diminishment, but as an active, behavioral choice to put others forward. Ben provides specific, practical ways to express humility while maintaining confidence and pride, and explores how the rise of AI makes authentic human humility more important, not less.
Episode Notes
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Key Highlights
- The humility myth debunked: Humility is not about retreating, withdrawing, or diminishing yourself - it's an active behavior of putting others higher, not putting yourself lower
- Selfless self-promotion: You can still be proud and confident while expressing humility - shift from singular to inclusive pronouns, frame success around organizational impact, and highlight what you learned in the process
- Extend credit in the widest sphere possible: Don't just credit the most visible contributors - look for ways to shine a light on those with first, second, and tertiary connections to the work
- The compounding effect: What feels like a short-term cost of humility becomes a long-term reputation as someone who scales impact and cultivates excellence in others - it bounces back and reflects on you
- AI amplifies the need for humility: As AI democratizes capability and knowledge, what differentiates leaders will increasingly be uniquely human qualities - those who acknowledge AI's capabilities while shining a light on others' unique human contributions will stand out
Notable Quotes
- "Humility is not thinking less of yourself - it's thinking of yourself less." - Rick Warren
- "Being humble means recognizing that we are not on earth to see how important we can become, but to see how much difference we can make in the lives of others." - Theologian quoted in Field Note
- "You don't have to put yourself back in order to push someone forward. Both of those things can be true at the same time."
- "If I only extend credit in those instances where I'm expecting a really high return, that feels transactional. In order for humility to be credible, it needs to be demonstrated consistently."
- "We can drive way more impact when we're moving others and amplifying others to be their most successful - we only get a one-to-one return when we do that on ourselves."
Featured Speakers
- Ben Stringfellow is an Executive Coach and Partner at CRA | Admired Leadership, known for his ability to turn either-or conversations into both-and conversations and his talent for making complex leadership concepts immediately actionable. A passionate advocate for the behavioral view of leadership development, he uses Alex daily as an "intentional contrarian" - asking it to prove him wrong and push his thinking in new directions. His coaching approach is grounded in the belief that leadership is simply making people and situations better.
- Wes Bender serves as a facilitator and thought leadership coordinator at CRA | Admired Leadership, helping to connect practical leadership insights with real-world application through webinars and educational content.
Resources Mentioned