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The Apprentice Gap: Developing Judgement in an AI-Enabled Workplace

LevelUp Leadership · 2026-07-11 · 11 min

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Episode notes

Learn how to develop genuine leadership judgement in younger people without removing the formative experiences that build it. AI is removing the grunt work that once taught people how organisations actually function. That is useful, but it carries a cost: we risk producing technically capable people who lack the judgement to know when and why to use the tools they have. This episode, timed for World Youth Skills Day on 15 July, explores what leaders owe the next generation beyond faster systems and better prompts. Drawing on conversations with previous guests Tamara Miles and Fred Miller, Lee unpacks the difference between age and career stage, why agency cannot simply be handed over like a token, and why osmosis-based development no longer works in an AI-enabled workplace. The central challenge for leaders is not about generational stereotypes; it is about asking better questions of the individual in front of you.

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