Overconfidence doesn’t always look like arrogance. Sometimes, it shows up as experience, a strong track record, or a bulletproof roadmap.In this episode, Christopher Donaleski breaks down how unchecked confidence can quietly derail even the best strategies. From a major U.S. retailer’s failed international expansion to research-backed patterns in executive decision-making, we explore how good intentions and proven success can still lead to costly outcomes.You’ll learn:Why overconfidence is often rewarded until it backfiresHow feedback loops close too early in high-trust teamsWhat “confidence without validation” looks like in actionThree ways to prevent confidence from becoming a blind spotThis episode is a practical look at one of the most overlooked risks in leadership. Because when assumptions go unchallenged, the cost isn’t always immediate—but it’s often irreversible.

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