As AI reshapes diagnostic, decision-making, and learning routines across high-stakes industries, this chapter reframes intergenerational difference not as fixed age-based traits but as learning and confidence dynamics that emerge when workers encounter AI-augmented workflows from different starting points. Drawing on Situational Leadership, Self-Efficacy Theory, Servant Leadership, and the Collaborative Synergy Learning Model (CSLM), the chapter extends these into a Collaborative Synergy Learning Ecosystem (CSLE) for sustained workplace transformation. Central to the argument is AI trust calibration — ensuring workers neither over-rely on nor reflexively reject AI outputs — which requires motivationally grounded reskilling and psychological safety so workers can question AI without fear of embarrassment. The chapter offers practical and scholarly contributions for safety leadership, workforce development, and organizational AI governance.
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