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Mistake or Error? How Leaders Show Up in the Moments That Matter

Introduction:

Chris Dyer is a renowned culture expert, leadership speaker, and best-selling author who has served as a CEO and consultant, most notably building a remote company of over 4,500 people before remote work became mainstream. His companies have been named a Best Place to Work fifteen times and recognized on Inc. Magazine’s list of fastest-growing companies five times, while Chris himself has been named Inc.’s #1 leadership speaker on culture and has written three best-selling books. Known for his innovative approach to building positive work environments and leading organizational change, Chris draws on his experiences as a pioneer in remote work to teach audiences how to create cultures where employees thrive. He is passionate about sharing actionable strategies and stories that help leaders foster trust, engagement, and high performance in the workplace.

 

Here’s a glimpse of what you’ll learn:

  • [2:19] How Chris Dyer transitioned his company from brick-and-mortar to fully remote during a recession
  • [3:17] Why great company culture was built through experimentation — not expertise
  • [5:23] Debunking the myth that leaders are born, not made
  • [8:45] Why remote work became a game-changer for Chris’s business success
  • [12:10] The importance of empowering employees with trust and autonomy
  • [15:05] How Chris designs keynote speeches to create commitment and lasting behavior change
  • [20:05] How small leadership changes can drastically improve team engagement
  • [25:00] Creating a culture where employees feel safe to make mistakes
  • [28:50] The role of transparency in building trust with your team
  • [34:30] How to overcome leadership misconceptions and evolve as a leader

In this episode…

What’s the difference between a mistake and an error? And why might that distinction define your entire company culture? When something goes wrong, most leaders react quickly — sometimes too quickly. But what if the real leadership opportunity lives in the pause?

 

For Chris Dyer, a globally recognized leadership speaker and bestselling author on company culture, culture is built in the moments that matter — especially when pressure is high and people are watching. He shares the unforgettable story of getting stuck on a zipline in Portugal and how that experience helped clarify a powerful leadership philosophy: panic is often wrong, and trust must be intentional. From a $25,000 employee “mistake” that could have ended in termination to eliminating traditional one-on-one meetings, Chris explains how leaders create psychological safety by slowing down, distinguishing mistakes from errors, and choosing curiosity over blame. These small but defining moments compound into lasting culture.

 

In this episode of Sticky: Stories That Stick, Amelia Forczak sits down with Chris Dyer to explore how leaders show up when it counts. They discuss building trust-driven organizations, protecting employees publicly, redesigning meetings for better performance, and using storytelling to make leadership lessons stick. If you manage people — or aspire to — this conversation will change how you respond the next time something goes wrong.

Resources mentioned in this episode:

Quotable moments:

  • “There’s definitely this misunderstanding that leaders are born; that is total garbage. The best leaders are willing to change and evolve as people.”  
  • “Mistakes are gold. We want people to try. I just want you to go make the decision — try it.”  
  • “If you know your culture is wrong, it’s like the vibe is wrong. We want people to at least be okay with going to work.”  
  • “Say yes to every question that comes to you and see what happens — you’ll watch your mind get blown by how differently people interact with you.”  
  • “It can take you an extra two or three minutes as a boss, but you’re training people to be creative and innovative because they know you’re receptive.”

Action Steps:

  1. Default to trust instead of micromanagement: Giving employees autonomy to make decisions builds confidence, speeds up execution, and strengthens loyalty across the organization.
  2. Distinguish between mistakes and errors: Treating well-intentioned mistakes as learning opportunities while holding true errors accountable creates psychological safety without sacrificing standards.
  3. Audit and streamline your meetings: Regularly evaluating which meetings are necessary reduces wasted time, increases productivity, and empowers teams to focus on meaningful work.
  4. Encourage a “yes” mindset in leadership: Responding with openness to ideas fosters innovation, strengthens communication, and motivates employees to contribute creatively.
  5. Pause before assigning blame: Slowing down to gather full context before reacting prevents costly decisions, preserves strong employees, and reinforces a culture of fairness and trust.
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