In Summer 2005, Phillips Academy hired James W. Wickenden of Wickenden Associates to analyze the school’s administrative structure and functionality.

Head of School Barbara Chase said, “Because it was clear that the Strategic Plan was going to take a lot of funding to become a reality, I knew that a restructuring needed to be done and he was somebody that I brought in that had a lot of experience with schools and school administrations, who I thought would have good thoughts about...