AI and the Future of Work
Explore how AI is reshaping the job market, from automation and displacement to new career opportunities. Hosts discuss historical context, ethical questions, and real-world examples that illuminate the complex relationship between AI and employment.
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Chapter 1
Automation at Work
Timothy Chester
When I was hired as CIO at Pepperdine University, I stepped into a role shaped by crisis. I inherited a PeopleSoft implementation that was completely off the rails. Technically, the project was intact. It was on budget. The timeline still held. But across the university, the perception was clear: the project was a massive failure.
Timothy Chester
Not because the servers were down—but because trust had evaporated.
Timothy Chester
My predecessor had hired brilliant PeopleSoft engineers—some had written the product’s source code. But that deep expertise created a false confidence that success was about the technology. It wasn’t. I brought a sociologist’s lens, re-centered the project around empathy and communication, and made staffing changes to elevate people-first leaders. The turnaround succeeded—because we rebuilt trust.
Timothy Chester
In today’s dispatch, we want to apply that human-centered lens to the question everyone’s asking now: What does AI mean for the future of work? Beneath the hype and hand-wringing lies a deeper shift: knowledge workers must up their game—in both value and versatility—or risk seeing their roles quickly made obsolete.