Unlearn · 2026-06-10 · 40 min
Jim Highsmith has been thinking about decision-making for a long time. When he wrote Agile Project Management in 2004, he went looking for practical guidance on decision-making in the project management literature and found very little. That gap matters even more now. In this episode, Jim and I talk about why AI raises the stakes for executive judgment. AI can remove friction, speed up work, and take on repeatable tasks, but it can also make it easier for leaders to stop practicing the very capabilities they are paid to use. Jim brings this to life through John Boyd’s OODA loop, the risk of judgment atrophy, mountaineering decisions, Rob Hall’s Everest threshold, Phil Knight’s pattern recognition at Nike, and a personal story from Jim’s own time leading a collaborative project team at Nike. This conversation is really about how leaders build judgment deliberately: by making consequence-bearing decisions, setting thresholds before pressure arrives, creating space for slow thinking, and reflecting honestly on how decisions were made.
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