The Mammoth in the Room

As your organization grows, you’ve probably experienced the moment when consensus-based decision-making starts breaking down. What worked for your startup team of 10 suddenly becomes chaos with 100 people. This isn’t leadership failure; it’s an evolutionary inevitability.

Why do we follow leaders at all? Today, we kick off a new mini-series on the history of leadership from prehistoric campsites to the rise of kingdoms. As leaders and decision-makers, understanding why humans abandoned egalitarian structures for centralized authority helps us better grasp the hidden forces shaping organizations today.

Overconfidence isn’t just a leadership trait. Sometimes, it’s a strategic weapon for manipulation. But the very confidence that drives business leaders to the top can be their downfall when unchecked. Today, you’ll hear how figures like Elizabeth Holmes and Adam Neumann leveraged overconfidence to build empires that ultimately crumbled beneath them.

Confidence is often a prized trait in leadership, but what happens when that confidence isn’t backed by competence? In today’s episode, we discuss the allure of overconfidence, examining how it can cloud judgment, mislead hiring decisions, and distort organizational culture.

We uncover yet another dangerous leadership blind spot: overplacement. I’m referring to the notion that we and our teams are superior to the competition. Using Kodak’s tragic downfall as a case study, we’ll discover how leaders can become too proud of past wins, too dismissive of rising threats, and too slow to adapt.

Drawing on real-world examples such as the Deepwater Horizon incident and startup failures, we examine how success often breeds a false sense of certainty. We explore the planning fallacy, the inside view, and how ignoring base rates can lead to missed deadlines, bloated budgets, and strategic misfires.