Episode Summary
Jack Skeels is the founder of AgencyAgile and author of the new book Unmanaged: Master the Magic of Creating Empowered and Happy Organizations. With a background in robotics programming, management consulting, and think-tank research at RAND Corporation, Jack brings a data-driven, experience-rich approach to one of the most misunderstood aspects of running an agency: managing people.
In this episode, Russel and Jack explore the evolution of management, how most agencies fall into the trap of accidental management, and what it really means to lead in a project-driven business.
Episode Highlights:
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- Why “more managers” often means less productivity and how to avoid the trap
- The real reason agencies struggle after hitting 15–20 employees (hint: it’s not client work)
- A brief but powerful history of how we got modern management wrong
- Jack’s four key “managerial moments” that can transform team output
- Why your best employee might make your worst manager and what to do instead
Agency Info
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Company: AgencyAgile
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Guest: Jack Skeels
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Year Started: 2012
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Employees: 11-25
The more managers you have, the less happy your workers are, and the lower the quality of work.
Jack Skeels
Key Takeaways
“The Management Tax” is Real
As agencies grow, they often add layers of middle management in the hopes of creating order. Jack calls this the “management tax”,the hidden productivity cost of too many people managing and not enough doing. More management doesn’t mean more control, it means less agility.
Project-Driven Businesses Require a Different Operating System
Unlike product or process-driven companies, agencies face a unique challenge: every project is different. That means traditional process-driven management models break down. Teams need adaptive leadership, not rigid structure.
The Origin of Management Wasn’t Designed for Knowledge Work
Drawing from history, Jack traces modern management back to industrial-era factory thinking. The problem? Agencies aren’t factories—they’re idea machines. Applying assembly-line logic to creative work is a recipe for burnout and confusion.
Promoting the Best Individual Contributors Creates Dysfunction
Agencies often promote top performers into manager roles. According to Jack, that’s a mistake. Why? The traits that make someone excellent at execution often conflict with what’s required for effective leadership. Instead, he recommends creating dual career paths…one for deep specialists, another for people who love enabling others.
Real Management is About Asking Better Questions
The most impactful managers aren’t the ones barking orders—they’re the ones asking the right questions at the right time. Jack introduces four critical “managerial moments” that, when handled correctly, massively improve team clarity and output.
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