I Have Some Questions...

074: "The Future CEO Will Be a Chief Executive Orchestrator" ft. Chris Dyer

• Erik Berglund

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0:00 | 1:30:16

In this episode of I Have Some Questions..., Erik sits down with culture strategist and bestselling author Chris Dyer to unpack the hardest leadership question of our time: how do you lead through relentless, accelerating change? From the elephant sitting on your chest to the myth of perfect AI adoption, this conversation dives into practical, human-first strategies for thriving in chaos. Chris challenges CEOs to fire themselves from the job they think they have and step into a radically different role—one that empowers experimentation, transparency, and better work for everyone.

👤 About the Guest

Chris Dyer is a global authority on company culture, leadership, and remote work. As a keynote speaker, podcast host, and founder of several successful businesses, Chris has advised countless executives on how to build workplaces where people actually want to show up. He’s the author of The Power of Company Culture and Remote Work, and has been featured by Forbes, Inc., and the BBC. His work is grounded in real-world leadership, not theory—and it shows.

🧭 Conversation Highlights

  • Why most CEOs feel like an elephant is sitting on their chest 🐘
  • The real reason change feels so overwhelming today
  • Why “fire yourself” is the first step toward better leadership
  • The meeting audit that can change your company overnight
  • What most leaders misunderstand about AI adoption

💡 Key Takeaways

  • Leadership isn’t about direction—it’s about orchestration. Instead of knowing exactly where to go, leaders must run experiments that help the organization figure it out.
  • Most meetings are a tax on productivity. Auditing and eliminating them is one of the fastest ways to boost effectiveness.
  • You can't AI your way out of inefficiency. Automating broken processes just makes brokenness faster.

❓ Questions That Mattered

  • Is this the most stressful business climate we’ve ever faced—or are we just experiencing change differently?
  • Where does thriving in change begin: clarity of direction, or clarity of value?
  • What does it actually mean to "fire yourself" as a CEO—and how do you start?
  • How do we give people time to do their best work, instead of trapping them in meetings and emails?
  • Can empathy become a crutch for leaders, and if so, how do you balance it?

🗣️ Notable Quotes

“You are always at war with mediocrity. That’s what will creep back in if you don’t lead.” —Chris Dyer

“The future CEO isn't a chief executive officer. They're a chief experimentation officer.” —Chris Dyer

“Every company needs AI. But plugging in a tool without a culture to support it will fail.” —Chris Dyer

“We have to start creating the best place to work—right now. Not after AI. Not after the next wave.” —Chris Dyer

“Transparency isn’t about sharing everything—it’s about stopping people from filling in the gaps with fear.” —Chris Dyer

🔗 Links & Resources