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 review the existing job description for the Head and create one that focuses on the school’s critical issues and plays to the skill-set of the new Head.

Encourage the departing HOS to avoid retaining weak faculty or staff.

Whenever there is a Head of School turnover, one of the greatest gifts a Board could give to the new leader is to direct the departing Head to avoid retaining faculty or staff members whose effectiveness has declined significantly.  Undeniably, the Head who is departing will be less than enthusiastic about the non-retention of mediocre performers.  As a result, the Board needs to focus on what is best for the School as opposed to what is convenient for the departing Head.

Examine the Administrative Structure of the School.

The administrative structure of a school should be examined periodically by the Board, and especially when a new Head is appointed.  Stated another way, what organizational structure works for one Head, may not be appropriate for another.  Thus, when a new Head of School is appointed, the Board of Trustees and the new Head have an opportunity to discuss a structure that might be more effective in addressing the challenges facing the school as well as giving the new Head an opportunity to engage in tasks in which he or she has a passion and expertise.

Review the process by which the HOS will be evaluated.

The longer the Head has been at the school, the less rigorous and the less frequent the Board is likely to evaluate the Head.  Thus, when conducting a search for a HOS, the Board should use this as an opportunity to develop an instrument to be used to evaluate the new HOS.


Appointing an effective Chair or Co-chairs.

The selection of an effective Chair or Co-chairs for a HOS search is as important as the recommendation to the Board of the new Head of School.  The Chair must be a highly respected member of the Board, a person who listens, thinks, reflects, and sets standards and norms, and who has the wisdom and courage to confront others when necessary.

Communicating with the constituencies of the School.

With the possible exception of the students, a Head of School search galvanizes the attention of the school’s constituencies.  Given that, the Chair of the Search Committee should plan on communicating monthly to the school community on the progress of the search.  Under no circumstances, however, should this communication contain the names of candidates.

Reviewing the “Opportunity Statement”.

Search firms are familiar with search processes, including the establishment of a search calendar, and have a database of potential candidates.  Those on the search committee, however, are the experts of the school.  Thus, the search firm and the search committee must collaborate on the drafting and editing of a document that describes the school, identifies the challenges facing the new HOS, and specifies the criteria of the ideal candidate.  The Opportunity Statement is designed to educate those interested in a given school; it is not, however, a sales pitch that focuses solely on the positives.

Respecting the need for a faculty voice on the Search Committee.

Some search committees are composed solely of trustees.  While that decision is the prerogative of the Board, we nonetheless recommend that the search committee include one or two faculty members.  The committee needs a faculty voice to address questions such as those associated with the curriculum, the professional development of the faculty, and the need for equipment, space, and materials. Faculty members can address those issues with far more knowledge than that of a trustee.

Determining the biases of the Search Committee.

The word “bias” should not be viewed as a negative.  Everyone has biases. Prior to interviewing any candidates, the Co-chairs should structure a process to enable them to be aware of the strongly felt biases of the committee members.  This is especially true for faith-based schools, single-gender schools, and schools that serve students with special needs.

Developing a tool to evaluate the finalists.

One of the biggest mistakes a search committee could make is to use a personality or behavioral instrument validated on a population different from that of Heads of School.  Search committees committed to having an inventory could retain an organizational psychologist to conduct interviews of trustees to determine which competencies are essential. This research should result in an instrument that, when used by the search committee, generates relevant data for each of the finalists.

Conducting reference checks of finalists.

Undeniably, reference checks are time-consuming.  They can also add to the cost of a HOS search. However, if done well, they are worth every penny.  Most search firms include reference checking in their deliverables. Only a few, however, go “off-list” while most contact only the references provided by the candidate.  Going off-list is essential.  Also, the search firm and the search committee should work in partnership to determine who is responsible for reaching out to people who are able to provide a balanced assessment.


Why is alignment essential?

Schools are populated by bright people who are full of ideas.  However, if the ideas don’t mesh well with the mission of the school and its existing policies and procedures, then the skeptics will justifiably ask, “Why are we doing this?”  Thus, leaders of a school must create a culture in which the goals, initiatives, core values, and evaluation instruments all relate to the mission and challenges that the Board expects the Head to address.

The challenges facing the new HOS.

The professional development of the HOS should be linked to the challenges facing the school.  Bright, conscientious leaders can develop new skills.  Arranging for such to happen, however, requires the Chair of the Board to ensure that the Head develops the essential skills or in some cases makes an arrangement for others at the school to address challenges that might not be in the Head’s wheelhouse.

The goals of the Strategic Plan.

The goals of the school’s strategic plan should flow from the major challenges facing the school.  If there is no alignment between the goals of the strategic plan and the challenges facing the school, confusion will reign with respect to the priorities of the institution.  This confusion unfortunately will contribute to not only a decline in morale but also a divided community.

The mutually determined annual goals for both the Board and the HOS.

Each year the Board should reach an agreement on its goals and meet with the Head of School to mutually determine their annual goals.  If at all possible, these goals should be aligned with the agreed-upon challenges as well as the goals of the strategic plan.

The criteria on which the HOS will be evaluated on an annual basis.

Once the Board and the HOS mutually agree on the annual goals of the Head of School, the Chair of the Board should create a subcommittee to develop an assessment tool that measures the extent to which he or she achieved the goals set forth at the outset of each year.


In sum, the launching of a Head of School search is much more than finding a new leader of the school.  It also is an opportunity for the Board to initiate changes that, regardless of the reason, have been neglected.  In so doing, we hope that the Chair of the Board will work in collaboration with the new Head of School.

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.

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