Dispatches from an Internet PioneerDeep Dive: Being Cautious vs Driving Change
This episode dives into one of the most pressing dilemmas facing higher education technology leaders today: how to balance the drive for innovation with the need for operational resilience. It unpacks why colleges and universities so often default to caution—protecting legacy systems, processes, and risk-averse cultures—and explores the consequences of that mindset, from rising tuition and administrative bloat to eroding public trust. Through the lenses of the Gartner Hype Cycle and Christensen’s Innovator’s Dilemma, the episode examines why timing matters, why higher ed can’t afford to invest like a venture capital firm, and what gets lost when innovation is confined to pilot projects. Listeners will come away with a deeper understanding of the cultural and strategic forces at play—and practical insights for leading through the tension rather than avoiding it.
About the podcast
Technology is reshaping higher education, leadership, and the economy—but the biggest challenges aren’t just technical, they’re cultural and structural. Created by Timothy Chester, this podcast explores the real impact of AI, automation, and digital transformation on universities, work, and society. With a sociologist’s lens and decades in higher ed IT leadership, he cuts through the hype to uncover what truly matters.