In this episode, Nick sits down with David Reilly from World Wide Technology to explore how trust and structure must guide every AI transformation. Riley shares the five-question framework he used to evaluate technology decisions, from cost and reliability to risk and talent, and why it’s more critical than ever as enterprises race to adopt AI. Together, they discuss how CIOs can balance innovation with stability, build confidence with business partners, and lead teams through change without losing trust along the way.

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