AI at Work: Why Experimentation Beats Training Programs for Teams with Bill Gallagher

Episode notes

In this short “Three Big Questions” bonus episode of Talent in the Age of AI, host Jason Keese is joined by leadership and entrepreneur Bill Gallagher to discuss how leaders can build real AI capability on their teams without waiting for a definitive training program. Bill argues that traditional certification-style AI training is premature because tools and use cases change so quickly, and that teams build confidence through frequent experimentation, idea sharing, and the direct application of AI to everyday work. He describes what good AI use looks like in practice—using it for client planning, proposals, translation, purchasing decisions, and event planning—by trying it in the moment and switching tools when needed. Bill also warns that AI can worsen busyness by pulling people into endless “what if” rabbit holes, and emphasizes the importance of knowing when to stop, shift, and move on.