My Favorite Mistake: Learning Without Blame in Business and Leadership

Why Curiosity Drives Better Leadership (Debra Clary)

My guest for Episode #330 of the My Favorite Mistake podcast is Debra Clary, a leadership strategist, researcher, and executive coach with more than four decades of experience at organizations including Frito-Lay, Coca-Cola, Jack Daniel’s, and Humana.
Episode page with video, transcript, and more
She’s also a TEDx speaker, former off-Broadway performer, and the author of the new book The Curiosity Curve: A Leader’s Guide to Growth and Transformation Through Bold Questions.
In this episode, Debra shares one of her favorite mistakes—an unexpected wrong train stop in Italy that turned into a memorable discovery—and how that happy accident helped shape her approach to curiosity, flexibility, and exploring the unexpected. That theme carries through the conversation as Debra and I discuss how curiosity shows up in leadership, why assumptions can derail teams, and why “having the answers” is often the wrong place to start.
Debra walks us through the research behind The Curiosity Curve, including how her team developed a validated diagnostic for measuring curiosity and what they learned about its connection to engagement, retention, innovation, and decision speed. She shares practical examples of how leaders unintentionally shut down curiosity and how small shifts in inquiry can unlock better thinking and stronger team performance.
We also explore how curiosity interacts with psychological safety, how leaders can avoid the trap of reflexive certainty, and why curiosity becomes even more important in high-pressure or high-uncertainty situations. Debra closes by discussing the role curiosity plays in an AI-driven world—why it remains uniquely human, and how tools like AI can actually help people deepen their inquiry rather than replace it.
If you’re interested in how leaders can cultivate better questions, better conversations, and better outcomes, this episode will spark ideas you can put to use right away.

Questions and Topics:
What’s your favorite mistake?
Were there similar moments in your career where a “missed stop” led to an unexpected opportunity?
Was starting as a Frito-Lay route driver a deliberate development path, or was that unusual?
Where did your passion for curiosity begin?
Is there a way to gauge curiosity in a team or organization?
How do you measure something like curiosity in a meaningful way?
How do you help leaders learn to be more curious instead of just telling people to “be curious”?
When hiring, is it better to select already-curious people or rely on the culture to develop curiosity?
Is there such a thing as too much curiosity—can it slow execution or decision-making?
From your research or coaching, what’s an example of curiosity being missing and causing problems?
How do you help leaders understand that curiosity and psychological safety are building blocks for innovation—not optional extras?
Do you see leaders struggle with the difference between knowing, assuming, and figuring things out?
In urgent or high-pressure situations, does stress make it harder for people to stay curious?
Do you have examples where curiosity helped prevent a small mistake from turning into a big one?
Have you seen situations where people used questions in unhelpful or critical ways while claiming they were being “curious”?
How do you think about Ed Schein’s idea of humble inquiry?
Can AI replace curiosity—or does curiosity still give humans a unique advantage?
Can interacting with AI actually help people strengthen their curiosity?

From Toxic Culture to Empathic Leadership: Lessons in Empathy and Accountability (Dr. Melissa Robinson-Winemiller)

My guest for Episode #329 of the My Favorite Mistake podcast is Dr. Melissa Robinson-Winemiller, a TEDx speaker, empathy and leadership expert, and author of The Empathic Leader: How EQ via Empathy Transforms Leadership for Better Profit, Productivity, and Innovation.
Episode page with video, transcript, and more
Melissa shares the story of her “favorite mistake” — leaving her music and academic career after experiencing a toxic culture and institutional failure to protect her following an assault by a colleague. What began as heartbreak became the foundation for her life’s work: helping leaders build empathy, trust, and psychologically safe workplaces.
We discuss how empathy differs from sympathy and compassion, and why leaders often misunderstand empathy as weakness. Melissa explains why true empathy isn’t about being nice—it’s about being kind—and how self-empathy is the first step toward leading others effectively.
Her framework for self-empathy includes observing, reflecting, building awareness, and practicing compassion toward oneself. That self-understanding helps leaders respond constructively when mistakes happen—creating cultures where learning and accountability can thrive.
“Empathy isn’t soft. It’s kind.”“Empathy doesn’t mean no boundaries—it means understanding through another’s perspective.”
Melissa also discusses findings from her doctoral research in interdisciplinary leadership at Creighton University and her viral TEDx Talk on self-empathy and self-judgment, which has drawn tens of thousands of views within days of release.

Why Unlearning Old Habits Is Harder Than Learning New Ones

In this edition of Mistake of the Week, Mark Graban tells a story that didn’t appear in any safety report or headline — it happened on a pickleball court. Early in learning the sport, Mark found his old tennis instincts taking over, leading to a very incorrect serve and a moment of embarrassment. What followed was a small but meaningful lesson in feedback, psychological safety, and the challenge of unlearning deeply wired habits.
Supportive coaching, timely correction, and a friendly playing environment turned an awkward mistake into a productive one. Mark reflects on why unlearning is often harder than learning, and how leaders can create conditions where people feel safe enough to improve.

How 531 Living Patients Were Mistakenly Declared Dead

In this week’s Mistake of the Week, Mark Graban tells the story of a Maine hospital system that accidentally mailed condolence letters to 531 very-much-alive patients. The cause? A computer glitch — and a few missing fail-safes. Mark explores what this bizarre mix-up reveals about system design, automation, and trust in healthcare. Beyond the absurd headline lies a familiar pattern: when we blame people instead of learning from process failures, we guarantee more mistakes. So what does “fully resolved” really mean? And what can leaders learn from a mistake that’s literally to die for?If you received this episode through your podcast app and not a séance, you’re doing fine.
 

Looking Back: Katie Anderson & Isao Yoshino on Learning, Leadership, and Mistakes

We’re going back to Episode 30 from January 2021, featuring Katie Anderson — author of Learning to Lead, Leading to Learn — and Isao Yoshino, the longtime Toyota leader whose career and lessons inspired her book.
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It was such a privilege to talk with them then, and even more meaningful now, because I recently got to spend time with Mr. Yoshino in Japan last October during Katie’s Learning to Lead, Leading to Learn experience. Seeing him there — humble, curious, and still passionate about developing others — really reinforced everything we talked about in that episode.
Mr. Yoshino shared a story from early in his Toyota career, when a mistake on the shop floor could have led to punishment, but instead led to learning. His leaders didn’t blame him — they worked with him to fix the system. That experience shaped how he led and coached for decades.
Katie shared her own favorite mistake — a story about feedback early in her career that helped her realize the power of listening, asking questions, and helping others find their own answers.
Together, we explored what it means to create a culture where people feel safe to learn, improve, and grow — the kind of culture that turns mistakes into progress.

From the Wrong Business to the Right Voice: Finding Purpose Through Mistakes (Emily Aborn)

My guest for Episode #328 of the My Favorite Mistake podcast is Emily Aborn, a small business copywriter, speaker, and host of the Small Business Casual podcast.
Episode page with video, transcript, and more
Emily helps entrepreneurs bring clarity, creativity, and authenticity to their marketing. Before finding her true calling, she owned a brick-and-mortar organic mattress store—a business that looked great on paper but didn’t align with her passions or strengths.
Emily shares how this “perfect-on-paper” business became her favorite mistake. Though the store was profitable, she found herself feeling trapped, unfulfilled, and disconnected from the work she truly loved. Through closing that chapter, Emily discovered what she actually enjoyed most—writing, connection, and storytelling—and turned those insights into a business built around her natural skills.
Today, Emily works with entrepreneurs across industries to find their authentic voice and create meaningful marketing. In this episode, she and Mark explore lessons about self-awareness, alignment, and how mistakes can guide us toward a more fulfilling path. Emily also shares practical insights on copywriting, understanding your audience, and why genuine collaboration beats fear-based marketing every time.

Questions and Topics:
What was your favorite mistake, and what did you learn from it?
Why did that business seem like such a good idea on paper?
What made you realize it wasn’t the right fit?
How did running that store help you discover your passion for copywriting?
What were some of the marketing lessons you learned from that experience?
What are the most common copywriting or branding mistakes you see small businesses make?
How can business owners find and express their authentic voice in their marketing?
What are “problem-aware,” “solution-aware,” and “symptom-aware” customers—and why does that matter?
How do you approach repurposing content the right way instead of just copying and pasting?
What has hosting your own podcast taught you about communication and creativity?
Have you ever made a memorable mistake as a podcaster yourself?

When AI Tried to Do Too Much: Lessons on Creativity and Humble Technology — Maya Ackerman

My guest for Episode #327 of the My Favorite Mistake podcast is Dr. Maya Ackerman, AI pioneer, researcher, and CEO of WaveAI. She’s also an associate professor of Computer Science and Engineering at Santa Clara University and the author of the new book Creative Machines: AI, Art, and Us.
EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE
In this episode, Maya shares her favorite mistake — one that changed how she builds technology and thinks about creativity. Early in her journey as an entrepreneur, her team at WaveAI created an ambitious product called “Alicia,” designed to assist with every step of music creation. But in trying to help too much, they accidentally took freedom away from users. That experience inspired her concept of “humble AI” — systems that step back, listen, and support human creativity rather than take over.
Maya describes how that lesson led to their breakthrough success with Lyric Studio, an AI songwriting tool that empowers millions of artists by helping them create while staying true to their own voices. She also shares insights from her research on human-centered design, the philosophy behind generative models, and why we should build AI that’s more collaborative than competitive.
Together, we discuss why mistakes — whether made by people or machines — can spark innovation, and how being more forgiving toward imperfection can help both leaders and creators thrive.

“If AI is meant to be human-centric, it must be humble. Its job is to elevate people, not replace them.”— Maya Ackerman
“Who decided machines have to be perfect? It’s a ridiculous expectation — and a limiting one.”— Maya Ackerman

Questions and Topics:
What was your favorite mistake — and what did you learn from it?
What went wrong with your second product, “ALYSIA,” and how did that shape your later success?
How did you discover the concept of “humble creative machines”?
What makes Lyric Studio different from general AI tools like ChatGPT?
How do you design AI that supports — rather than replaces — human creativity?
What’s the real difference between AI and a traditional algorithm?
How do you think about ethical concerns, like AI imitating living artists?
What do you mean by human-centered AI — and how can we build it?
Why do AI systems “hallucinate,” and can those mistakes actually be useful?
How can embracing mistakes — human or machine — lead to more creativity and innovation?
What are your thoughts on AI’s future — should we be hopeful or concerned?

How a Leadership Mistake Taught William Harvey to Build Trust and Psychological Safety

My guest for Episode #326 of the My Favorite Mistake podcast is Dr. William Harvey, a manufacturing executive and university professor whose career is defined by developing people, strengthening systems, and driving organizational excellence. A proud U.S. Marine, William carries forward a deep tradition of service and leadership. He also serves as the chair for the 2026 AME International Conference in Milwaukee, hosted by the Association for Manufacturing Excellence (AME).
EPISODE PAGE WITH VIDEO AND MORE
William shares a powerful early-career story about a mistake that taught him lasting lessons about trust, humility, and psychological safety. When he accidentally derailed a customer order by taking home the wrong document, he feared the worst. Instead, his manager’s calm and compassionate response—and a customer’s extraordinary effort to make things right—changed how William thought about leadership forever.
Over time, William applied those lessons to how he leads teams and builds culture. He believes that leaders go first—by admitting mistakes, showing vulnerability, and creating space for others to experiment, fail, and learn. Through daily coaching cycles and methods like Toyota Kata, he helps people develop confidence in problem solving and take ownership of improvement. His goal: to build a workplace culture rooted in trust, respect, and continuous learning, where every person feels safe enough to speak up and strong enough to lead.

Key Lessons & Themes:
Why trusting your team is critical to avoiding unnecessary errors
How supportive leadership responses turn mistakes into growth moments
The connection between psychological safety, continuous improvement, and Toyota Kata
How to “go first” as a leader—admitting your own mistakes to build trust
The link between physical safety and psychological safety in world-class organizations
What leaders can learn from Paul O’Neill and his “zero incidents” mindset at Alcoa

Archives: From Shame to Self-Awareness — A Leadership Transformation with Sabrina Moon

In this bonus re-release, we revisit an important and timely conversation with Sabrina Moon, Founder and CEO of The Problem Solving Institute and a certified Dare to Lead™ facilitator.
Originally aired as Episode #35 of My Favorite Mistake, this conversation remains one of the most powerful and honest reflections on leadership, shame, and transformation.
Episode page with transcript and more
🔍 What You’ll Hear:
Sabrina’s “favorite mistake” — using shame as a leadership tool in high-stress environments
The culture of command-and-control leadership she inherited (and how she broke the cycle)
How Brené Brown’s work on vulnerability and shame helped her lead differently
The personal toll of shame-based leadership — on her team and herself
Why self-awareness is a skill—and how we can build it
The role of grace, compassion, and curiosity in becoming a better leader
“We use shame and the fear of shame to motivate, but I think in an unhealthy way. I would utilize shame because it was the last tool in my toolbox and I was desperate.” — Sabrina Moon
👤 About Sabrina Moon:
Sabrina is a leadership coach and consultant who helps organizations move from reactive command-and-control cultures to psychologically safe environments where continuous improvement and innovation can thrive.
Connect with her at ProblemSI.com or on LinkedIn.
✨ Why Re-Release This Episode?
As more organizations reflect on how culture impacts performance, engagement, and well-being, this episode offers essential insights for leaders at every level. Whether you're managing a team or transforming a system, Sabrina's story reminds us that who we are as leaders matters just as much as what we do.

Scaling vs. Scrambling: What a Business Mistake Taught Phillip Cantrell About Growth

My guest for Episode #325 of the My Favorite Mistake podcast is Phillip Cantrell, EVP of Strategy at United Real Estate, founder of Benchmark Realty, and author of Failing My Way to Success: Lessons from 42 Years of Winning and Losing in Business.
EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE
Phillip reflects on more than four decades of entrepreneurial ups and downs across printing, real estate, and related ventures. He openly shares how devastating mistakes—including putting “all his eggs in one basket”—forced him to reinvent his approach. What looked like a catastrophe in 2007–2008 became the turning point that fueled Benchmark Realty’s rapid growth to nearly 2,000 agents.
“Failure is going to happen. If you don’t make mistakes, you’re not doing anything.”
In this conversation, Phillip and I talk about the difference between scaling vs. scrambling, the dangers of playing “not to lose” instead of “playing to win,” and why documenting processes is essential for growth. He also explains why your only real competitor is “the man in the mirror” and how daily reflection helps him learn from mistakes and avoid repeating them.
This episode is packed with timeless lessons on leadership, resilience, and learning from failure—whether you’re in real estate or any other industry.
“If you play not to lose in business, you’re already losing.”

Questions and Topics:
What’s your “favorite mistake” from your career?
How did putting “all your eggs in one basket” impact Benchmark Realty?
What did you learn from losing agents and clients during the mortgage crisis?
How did you develop the flat-fee brokerage model, and what risks did you see at the time?
Did you ever doubt whether that new model would work?
How did you rebuild Benchmark from five agents to nearly 2,000?
Why is it important to look outside your own industry for best practices?
What do you mean by the difference between scaling and scrambling?
How does documenting processes create better outcomes?
Why do you say your only real competitor is “the man in the mirror”?
What role has reflection and journaling played in your leadership growth?
What advice would you give younger entrepreneurs about learning from mistakes?