Why Alignment is Important in Head of School Searches | Jim Wickenden | 8 Min Read

One of the reasons I have spent 35 years serving independent schools is the joy I receive from meeting trustees who devote their time, treasure, and talent to the schools they love.  Given my respect for the work done by those trustees, I decided to write about what might be done to help them have an even greater impact on the schools they govern.  My recommendations come not from the books on governance written by Richard Chait and others, but from what I have learned when launching Head of School searches and working with hundreds of search committees.

This article addresses three issues:

  • Governance Recommendations
  • Responsibilities for a Search Committee
  • The Need for Alignment


Being mission-driven is critical.

At the risk of stating the obvious, all that follows in this article flows from the mission of the school.

Review the effectiveness of the standing committees of the Board. 

Most of the schools I’ve served have standing committees that continue to exist regardless of changes in Board leadership.  One of the complaints of Heads is that some trustees are prone to micromanagement.  One way to address that issue is to avoid having standing committees duplicate the school’s administrative structure. Boards should create standing committees that address the functions of more than one office to avoid falling into this trap.

Conduct a debate about the effectiveness or lack of term limits.

Boards are populated by both worker-bees and some who are less conscientious.  While the Committee on Trustees nominates new trustees who hopefully will contribute in a meaningful way to the governance of the school, replacing worker-bees just because they have completed a specified term may result in a less effective board.  Rather than running the risk of reducing the quality of the team, why not have the Committee on Trustees assess the overall effectiveness of trustees whose terms are about to expire and invite the stars to remain on the Board for another term.

Review Job Description of the Head of School.

Over three decades, there have been significant changes in the responsibilities of the Head of School.  The challenges facing new Heads today differ from those who were appointed 10 or 15 years ago.  Complicating this issue is the tendency of some Boards to increase the responsibilities of the Head.  Thus, when appointing a new Head, the Board should use this as an opportunity to…

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Jim Wickenden

Jim is a Principal at DRG and Founder of Wickenden Associates, an affiliate of DRG. Having been the CEO of one of the premier education executive search firms in the United States, Jim brings unparalleled experience and networks to best serve clients. With over 30 years of experience identifying and guiding Heads of Schools and other senior administrators of schools across the country, Jim approaches each search with flexibility and openness that responds to the individual needs and concerns of schools and their leaders. Before founding Wickenden Associates, Jim served as the Dean of Admissions at Princeton University and Director of Student and Alumni Affairs at the Harvard Graduate School of Education. A graduate of Tabor Academy and Princeton University, Jim holds a master’s degree in Counselor Education from Rutgers University, a master’s degree in the General Purposes of Education from Harvard University, and a doctorate in Counseling Psychology from Boston University. As a former member of eight boards of independent schools with a wide range of missions and resource levels, Jim also knows firsthand the responsibilities shouldered by today’s trustees; and knows how to guide boards through tough transition processes and on good governance practices. Jim lives in Princeton, NJ, and when he is not at the office he enjoys reading enlightening books.