Better software starts with understanding the work.

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.

Automation can create impressive local gains while quietly shifting administrative effort to another part of the network. This conversation examines what happens when shipper-side AI agents change the work arriving at freight forwarders, carriers, and frontline logistics teams. Operations and technology leaders will leave with a practical way to evaluate automation across the full process, begin with bounded experiments, and preserve visibility and control for the people absorbing the change.