The Shift to Managing Managers

Moving from managing individual contributors to managing managers requires a fundamental shift that many leaders struggle with. In this episode, Kevin shares lessons from his own difficult transition, where staying too close to the work actually limited both his team's growth and his own.

The core challenge isn't autonomy versus control. It's leverage versus comfort. When you focus too far down into your organization, you become an information bottleneck, your managers lose ownership, and your own leadership growth stalls. The job fundamentally changes: your leverage no longer comes from making decisions, but from providing context.

Kevin covers the warning signs of overmanaging (managers escalating decisions that clearly belong to them, work slowing when you're unavailable), practical frameworks for delegating effectively, and why feeling indispensable is usually a red flag, not a success metric.

A key test: Could you step away for two weeks? Would your managers make good decisions without you? If not, you might be the problem.

• Using Agile Techniques to Build a More Inclusive Team: https://www.youtube.com/watch?v=Atfxtk2Q90k
• Every Decision Creates a Policy: https://itdependspod.com/episodes/every-decision-creates-a-policy/
• "Turn the Ship Around!: A True Story of Building Leaders by Breaking the Rules" by L. David Marquet: https://amzn.to/49XH2Ty
• Delegation Poker from Jurgen Appelo: https://medium.com/@jurgenappelo/unclear-team-responsibilities-use-delegation-levels-985537dbea38
• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net)
• Your host: Kevin Goldsmith (https://kevingoldsmith.com)
• ConFoo 2026 (https://confoo.ca/en/2026)