After nearly four decades working at the intersection of logistics operations and technology, Wai Wong has seen major technology transitions from multiple generations of TMS platforms to the move away from physical shipment files and, now, AI. In this episode, Wai shares how an early system rollout taught him an enduring lesson: adoption gets easier when technology follows the operator’s workflow instead of forcing the operator to follow the technology. John and Wai discuss passive change management, involving frontline users early, the challenge of maintaining training as teams turn over, and why AI will need to earn operator trust rather than demand it. The takeaway is practical: introduce change in smaller increments, involve the people doing the work, test frequently, and design technology around how work actually happens.