Should We Still Build Careers Around Deep Specialization?

For decades, career advice has been simple: specialize, build deep expertise, and become indispensable. But what happens when AI makes that expertise accessible to almost anyone? The value of knowing how to do something is shifting toward knowing what should be done, why it matters, and whether the result is actually any good.

In this episode of People Managing People, host David Rice speaks with Tony Castellanos, Head of People at Nextdoor, about why judgment, curiosity, and taste are becoming critical leadership capabilities. They explore how AI could invert the traditional hierarchy of specialists and generalists, why organizing teams around business problems makes more sense than defending functional boundaries, and what happens when the org chart stops dictating who gets to solve what.

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