Leading Through Change: Lessons from a Student Systems Implementation

Timothy Chester shares a pivotal experience from his journey to becoming CIO at Pepperdine, revealing how understanding the human and cultural challenges behind technical projects can transform leadership. This episode explores how navigating ambiguity and building trust during ERP implementations can advance careers and develop impactful leaders.

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Chapter 1

Introduction

Timothy Chester

There was a moment I knew I’d get the CIO job at Pepperdine. I had connected, not through technical brilliance, but with fit and presence. At lunch, Gary Hanson, the Executive VP, asked casually, “I don’t get why a PeopleSoft implementation is so difficult.” Based on my experience, I knew the answer:

Timothy Chester

“There’s a lot of stress and angst about a new student system. Every institution has its own way of advising, enrolling, tracking, and assisting students, and these processes reflect the institution's mission, identity, and strategy. The new system may be configurable, but implementation means asking people to change the way they do their jobs. That’s not just a technical challenge. It’s cultural and human.”

Timothy Chester

The room shifted. Up until then, they had seen the frustrations as a technical failure. No one had framed it as a human, cultural problem. What I offered was a new lens. And once they saw it, they couldn’t unsee it. Ten days later, I got the offer.

Timothy Chester

In today’s Dispatch, we reflect on how skills developed during an ERP implementation set people up to advance their careers and grow into the kind of leaders institutions will crave.