#519 From Bureaucracy to Agility: Jack Skeels on Leading in the AI Era

In this episode of The CTO Show with Mehmet, we dive into the future of management with Jack Skeels, CEO of Agency Agile and author of Unmanaged. Jack shares why traditional command-and-control structures are outdated, how hidden dysfunctions cripple organizations, and what it takes to unlock true productivity in the age of AI.

We explore why overmanagement is slowing teams down, the warning signs leaders should watch for, and how AI can either reinforce bad habits—or transform organizations when paired with agile, human-centric practices.

Key Takeaways

• Why most management practices are outdated—and what to do instead

• The “plateau of optimism” and “chasm of despair” in projects and transformations

• How to spot hidden dysfunctions that derail productivity

• Why AI won’t fix bad processes—and how to redesign work for real impact

• The power of asking why and questioning the status quo

What You’ll Learn

• How to move from bureaucracy to agility in your organization

• Practical techniques to boost productivity and reduce rework

• Why unleashing talent beats overmanaging

• How AI is reshaping teams, value chains, and leadership roles

About Jack Skeels

Jack is the founder and CEO of Agency Agile, where he has worked with nearly 200 organizations to help them run faster, better, and happier. With a career spanning programming, project management, consultancy, and research at the RAND Corporation, Jack brings a unique perspective to modern leadership. His award-winning book Unmanaged offers a blueprint for rethinking how teams thrive.

https://www.amazon.com/Unmanaged-Master-Creating-Empowered-Organizations/dp/B0CLSJJJ49

https://www.linkedin.com/in/jackaskeels/

Episode Highlights

• [02:00] Jack’s journey from programmer to RAND researcher to Agency Agile founder

• [07:00] Why outdated management persists and the role of education in leadership

• [12:00] Warning signs of overmanagement and how to measure real productivity

• [18:00] Why CEO buy-in is non-negotiable for transformation

• [20:00] The “plateau of optimism” and “chasm of despair” in projects

• [24:00] How AI changes management—and why undoing structures is key

• [31:00] Trust and manipulation in AI decision-making

• [37:00] Jack’s book Unmanaged and its core lessons

• [40:00] Advice for the new generation of leaders: think different and always ask why