In this episode, I have a fascinating conversation with Jim Highsmith. We dive into Jim’s six-decade career in software development, his role in the Agile movement, and how his early influences continue to shape his thinking on digital transformation today. Jim shares stories from the punch card era to the Agile Manifesto, offering insight into the evolution of our industry.

We begin by exploring Jim's early work at Exxon, debugging code with hexadecimal printouts, and his eventual pivot into structured methods and adaptive development showing a career built on embracing risk, fostering change, and learning through experience.

Jim recounts the serendipitous path that led him to the Agile Manifesto in 2001, where he collaborated with figures like Kent Beck and Martin Fowler. He shares how his early thinking around adaptive methodologies aligned with what became known as Agile, even before the term existed. Throughout, Jim highlights how technological shifts, especially the rise of the internet, fundamentally altered software's purpose requiring new development paradigms.

In reflecting on Agile’s legacy, Jim contrasts optimization (à la Deming’s statistical process control) with adaptation (rooted in people, learning, and responsiveness). He emphasizes the importance of context in applying any methodology, whether Agile, Lean, or DevOps, and cautions against rigid orthodoxy in favor of flexible thinking. The conversation also touches on Deming’s influence, the missed opportunity for Agile and DevOps convergence, and Jim’s role in fostering integration between the Agile Alliance and the Project Management Institute (PMI).

Looking to the future, Jim sees AI as a transformation on the scale of the internet, requiring organizations to adopt adaptive mindsets or risk irrelevance. He warns that those who fail at Agile will likely fail at AI if they don’t build adaptive learning into their culture. He advocates for reimagining agility not as a fixed set of practices, but as a living, philosophical approach responsive to continual change.