In this week’s Mistake of the Week, a company’s HR team accidentally sent a mass termination email to the entire workforce — including the CEO. The culprit was an offboarding automation tool left in the wrong mode, turning a routine test into a company-wide panic.

Mark Graban explores what this moment teaches about automation, human fallibility, and the danger of relying on memory in systems that affect people’s livelihoods. Instead of asking, “Who pressed the wrong button?”, the real question is, “Why was this mistake even possible?”

A funny story now, but a real lesson in error-proofing or the lack thereof.

Because even when no one’s actually fired, the fear can linger long after the email is retracted.

In this episode of My Favorite Mistake, Mark Graban talks with Jason Sherman, an entrepreneur, startup advisor, and educator, about the early startup mistakes that quietly shape everything that follows.

Episode page with transcript, video, and more

Jason shares hard-earned lessons about choosing co-founders, distinguishing “smart money” from money alone, and why MVPs should accelerate learning rather than encourage overbuilding. The conversation explores judgment, incentives, and alignment through a Lean lens — showing how optimism, unchecked assumptions, and unclear decision rights can undermine even strong ideas.

This episode is especially relevant for founders, leaders, and anyone working under uncertainty who wants to turn mistakes into insight instead of regret.

Why do New Year’s resolutions fail so predictably—and what does that teach us about change at work? In this Mistake of the Week, Mark Graban explores why treating change as a test of willpower is a reliable setup for frustration, both personally and in organizations.

Drawing on behavioral psychology and leadership examples, the episode connects failed personal resolutions to common organizational mistakes: big announcements, ambitious targets, and too little attention to system design and psychological safety.

The takeaway is practical and actionable: instead of trying to boost motivation or eliminate human error, leaders should focus on making the right choices easier and the wrong ones harder—starting small, iterating, and learning forward instead of blaming backward.