Episode Summary
Jack Skeels is the founder of AgencyAgile and author of the 2024 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 re-release 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 single most important thing that a manager can do is enable productivity in the workers.
Jack Skeels
Key Takeaways
“The Management Tax” Is Real
As agencies add layers of management to create order, they can unintentionally reduce productivity. Jack calls this the “management tax”: too many people directing the work, and not enough support for the people doing it.
Project-Driven Agencies Need a Different Approach
Agency work is complex, creative, and constantly changing. Rather than forcing rigid factory-style management onto teams, leaders need systems that help people make decisions and stay productive.
Modern Management Wasn’t Built for Knowledge Work
Much of today’s management thinking came from industrial-era factories. But agencies are built around expertise and ideas—not repeatable assembly-line tasks—so applying the same logic can create frustration, confusion, and unnecessary control.
Don’t Automatically Promote Your Best Specialists
Excellent individual contributors do not necessarily become effective managers. Create meaningful paths for deep specialists, while reserving management roles for people who are genuinely motivated and equipped to help others do their best work.
Great Managers Remove Barriers
A manager’s job is not to have all the answers or direct every detail. It is to ask what the team needs—clarity, time, resources, or fewer interruptions—to do excellent work.
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