The Leadership Gambit

S08E01: The Mistakes Companies Keep Repeating


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Most companies aren’t failing because people don’t work hard enough. They’re failing because the system is working against them.

In this episode, we break down five common ways businesses quietly sabotage their own success, often while chasing growth, efficiency, or revenue. From overmanagement and weak leadership to confusing tactics with strategy and trying to force change with tools, we unpack what actually holds organizations back.

If you’ve ever felt frustrated by pointless processes, constant “priorities,” burned-out managers, or change initiatives that go nowhere, this episode will help you understand why. More importantly, it gives you language and frameworks to make sense of what you’re experiencing at work, protect your energy, and think more clearly about leadership, strategy, and where real value is created.

This conversation is for people who want healthier workplaces, better leadership, and systems that don’t punish the people doing the actual work.

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The Leadership GambitBy Chris Miller, Dane Smith