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In this episode, we talk about the Sorites Paradox: the ancient puzzle about vague boundaries (“When does a pile of sand stop being a heap?”). We then explore why it matters more than ever for modern executives using AI. The paradox reveals a fundamental truth: some concepts have no clear dividing line, yet AI systems force artificial thresholds on them.

We discuss how AI, rather than resolving ambiguity, can actually amplify analysis paralysis, offering endless refinements that tempt leaders into searching for a perfect data-driven moment that doesn’t exist. These systems create an illusion of precision, masking the fact that key strategic decisions still rely on human values, risk appetite, and judgment.

The episode concludes with practical guidance: embrace satisficing over optimizing, set decision boundaries before analysis begins, and design Probabilistic + Human-in-the-Loop workflows that intentionally reserve ambiguous cases for human leadership. In a world of infinite data, decisive action becomes a competitive advantage.

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