(Lessons from my book, plus conversations with Phillip Cantrell and Damon Lembi)
One of the central themes in my book, The Mistakes That Make Us, is the shift leaders must make from needing to be right to being willing to test their ideas. That move–from certainty to curiosity–creates the conditions for innovation, continuous improvement, and psychological safety.
On the My Favorite Mistake podcast, I've had the privilege of speaking with leaders who've lived this shift in dramatic ways. Recently, two conversations stood out. Phillip Cantrell, founder of Benchmark Realty, shared how the 2007-2008 housing collapse forced him to rethink everything he thought he knew about his business. And Damon Lembi, CEO of Learnit, described how overexpansion during the dot-com boom nearly bankrupted his company, pushing him toward a “learn-it-all” mindset that still guides him today.
Their stories align closely with the principles I explore in my book, and they illustrate why humility is such a powerful (and underappreciated) leadership trait.
Why Leaders Struggle to Say “I Don't Know”
As I wrote in the book, too many CEOs and executives go years without uttering the phrases “I don't know” or “I made a mistake.” Entrepreneur Joel Trammell once told me, “The two most powerful phrases that CEOs need to use are ‘I don't know' and ‘I made a mistake.' You could spend a year with some CEOs and they'd never utter either of those phrases. A lot of CEOs think they have to have all the answers.”
But leaders who insist on always being right often shut down dialogue and experimentation. They might feel safer in the moment, but they create brittle organizations where mistakes get hidden, feedback is muted, and innovation stalls.
The alternative is to treat ideas as hypotheses–not as proof of competence. That's where humility enters the picture. As Jeff Gothelf, author of Sense and Respond, explained:
“Humility is not the abdication of vision or leadership. Humility simply means that, while you may have strong opinions, based on your experience and expertise, you're willing to change your mind in the face of evidence.”
That shift–from being right to being willing to learn–is exactly what Phillip Cantrell and Damon Lembi discovered through painful but transformative mistakes.
Phillip Cantrell: Reinvention Through Humility
Phillip Cantell founded Benchmark Realty in 2006 to serve high-end custom home builders in Tennessee. For a while, things looked promising. Then the housing market collapsed. Virtually overnight, demand dried up, and half of his agents walked out the door to join a competitor.
“I was getting pretty cocky. I thought I was going to ride off into the sunset with a nice little business. And then the rug got yanked out from underneath me.” — Phillip Cantrell
That was his wake-up call. Instead of clinging to his old assumptions or doubling down on what had worked before, Phillip sat down with “the man in the mirror” and rethought his entire approach. He rewrote his business plan, launched a new flat-fee model, and rebuilt Benchmark from the ground up.
That mindset shift–from “I know I'm right” to “I might be wrong”–turned out to be the foundation of Benchmark's long-term growth. By the time he sold the company in 2020, it had grown to nearly 2,000 agents.
And Phillip is clear about the leadership lesson he took from that experience: if nobody on your team feels safe enough to challenge your ideas, you have a problem.
“Unless you cultivate an environment where people feel safe to disagree, you'll make many unnecessary mistakes.” — Phillip Cantrell
Damon Lembi: Becoming a “Learn-It-All”
Damon Lembi's story has a different backdrop but a similar message. In the late 1990s, as a young and ambitious new CEO, he pushed Learnit into rapid expansion during the height of the dot-com boom. His father cautioned against it, urging patience and focus. But Damon admits he was stubborn, convinced he knew better.
When the bubble burst, the business nearly collapsed. Damon had to call his grandfather just to make payroll. Looking back, he calls it the “most expensive MBA” he could have imagined.
“At the time, I was a know-it-all. I was stubborn. I was cocky. I thought, ‘This is what we're going to do,' and I didn't listen.” — Damon Lembi
What changed for him wasn't just his business strategy, but his leadership identity. Damon embraced humility, learned to consider worst-case scenarios (what he calls “purposeful awfulizing”), and committed to being a “learn-it-all” instead of a know-it-all.
“You don't need to know everything–you need to be willing to learn anything.” — Damon Lembi
That philosophy carried Learnit not only through the dot-com bust but also through the 2008 recession and the challenges of the COVID era. Damon now emphasizes vulnerability, feedback, and resilience in his leadership–skills he partly credits to his background in baseball, where failure is constant and adjustment is everything.
“Make new mistakes. Learn from them. Don't repeat the old ones.” — Damon Lembi
Humility: The Magic Ingredient
Both Cantrell's and Lembi's stories highlight a theme that runs throughout The Mistakes That Make Us: humility is the magic ingredient that makes learning possible. It's not about lacking vision or lowering standards–it's about staying open to evidence, feedback, and change.
Karen Hold, another voice featured in my book, puts it this way:
“By making those small bets frequently, you can test your way to success. Innovators tend to equate being smart with being right, and that's not the case in innovation. You're going to get it wrong most of the time.”
When leaders accept that reality, they stop treating mistakes as failures and start treating them as fuel for iteration.
John Toussaint: From All-Knowing to Facilitator
Dr. John Toussaint, former CEO of ThedaCare and now a coach to healthcare leaders, embodies this same shift. Early in his tenure, John led as what he later admitted was an “all-knowing leader.” He made top-down decisions, assumed he had to provide all the answers, and carried the heavy weight of being right.
But over time, and with mentoring from board members experienced in Toyota-based Lean management, he realized that this style was unsustainable and ineffective. His role wasn't to have all the answers–it was to create an environment where others could solve problems, learn, and improve.
That shift transformed both his leadership and the organization. John moved from being the decision-maker at the top to being a guide and facilitator, helping others develop the skills and confidence to identify issues and test solutions themselves.
This is exactly the spirit of what I've called the “I might be wrong” habit. In fact, I've tried to adopt it myself–not out of false modesty, but to acknowledge the difference between what I know and what I only suspect to be true. As my Toyota mentors often reminded me:
“What do you know? And how do you know it?”
John's transformation highlights another key truth: when leaders admit they might be wrong, they model curiosity and humility. That invites others to speak up, test ideas, and engage in improvement–without fear of blame.
“If the creator of a new product or service is convinced they're right, failing to listen to the concerns of others can result in big mistakes and failures.” — The Mistakes That Make Us
Just as Phillip Cantrell rebuilt Benchmark and Damon Lembi rebuilt Learnit, John Toussaint rebuilt his leadership style. And in doing so, he created a stronger, safer, and more innovative culture around him.
The Takeaway
Whether it's Phillip rebuilding his company in the wake of a market collapse, or Damon rethinking his leadership after nearly losing it all, the lesson is the same: progress doesn't come from being right on the first try. It comes from humility, experimentation, and the courage to say “I could be wrong.”
That shift–from know-it-all to learn-it-all–doesn't weaken leaders. It makes them stronger, more resilient, and more effective.
So the next time you feel pressure to be right, remember the better alternative: test, learn, and adjust. Because as Damon reminded me:
“If you're always right, you're not listening hard enough.”
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Let’s build a culture of continuous improvement and psychological safety—together. If you're a leader aiming for lasting change (not just more projects), I help organizations:
Engage people at all levels in sustainable improvement
Shift from fear of mistakes to learning from them
Apply Lean thinking in practical, people-centered ways
