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Navigating a Head of School Search in Rough Waters

The key ground rules in the head of search process are simple:

  1. Hire the right search firm.
  2. Establish an appropriate timetable, typically eighteen months and no longer. 
  3. Develop an accurate, realistic and enticing profile. 
  4. Form the search committee and establish the rules of the game for all players.
  5. Outline the communications strategies. 
  6. Treat all candidates with respect.
  7. Ensure you do not lose strong candidates by dragging out the process or by not being up front, professional and fair to all.
  8. Sell all candidates on the reasons why they should want to head your school.
  9. Ensure a successful and smooth transition by making transition a priority.

This roadmap to conducting a successful head of School search has not changed but COVID-19 has certainly complicated it.  In normal times, most boards and search committees find the head search process exciting, but during these extraordinary times it is more stressful and challenging and perhaps not what boards want to be doing.  But they may not have a choice.

Hire the Right Search Firm

In selecting a search consultant to find a head of school (or CEO for a nonprofit), the determining factor is usually the chemistry of the consultant with the board chair, search committee chair and/or others on the committee. What is probably most important, however, is the consultant’s prior knowledge, or the knowledge that he or she works diligently to acquire about the school’s culture, mission, history and the political realities that may be landmines for the next head or CEO. 

Rarely done but a very good idea is to choose a search consultant who is already familiar with the school from other work or assignments and may be very well positioned to know the type of head candidates who are mostly likely to succeed in that school culture and meet the expectations of the board and staff. It is a plus not a drawback for the search consultant to know most of the client school’s “warts” and skeletons in its closet. During these times, the more your consultant already knows about your school’s history, incidents, climate and culture, the better.

While the search consultant does not always have intimate knowledge of school and organizational climate, on site work prior to the start of the search is crucial to gaining that knowledge and insight. It should include focus group meetings with the parents, faculty and staff, students and alumni. If onsite focus groups are not possible, then the consultant should conduct them virtually. The consultant will not receive sufficient insights simply by posting a standard online questionnaire on the school’s website to gather constituent input about the qualities most sought in a new head or the challenges that he or she is likely to face.

The consultant will use constituent feedback to develop a compelling head of school profile. Search committee members should be wary of a profile that focuses too much on the experience and skills to manage short-term crises. Schools still need a visionary, strategic leader who can turn crises into opportunities for the future.   

Most head of school profiles describe “God on a good day”.  No candidate will tick all of the boxes. Be prepared to be flexible with respect to the qualifications and traits stated in the profile. The personal chemistry between the board and the candidate is very often more important and ultimately leads to the appointment of the new head.

The Process

Ideally a school should launch a search when the market for new heads is most active and when the candidate pool is likely to be the largest.  For example, a search that begins in the summer months for the following year will likely attract candidates who, for whatever reason, do not have a job, and the majority of heads will behave ethically and give their schools at least twelve months’ notice. On the other hand, a search process that drags on beyond 18 months is enervating and may send a signal that the process has failed to attract desirable prospects. 

While transparency may require that a search committee have one or more teachers, parents, or alumni (who are not already on the board) on it, board members, especially experienced ones, understand the challenges and intricacies of the search while non-board members (unless very well trained at the outset) tend not to.  Littleford & Associates advocates having most, if not all, members of the search committee consist of board members because the board is charged with governance and the ultimate selection of the next head. 

The most successful searches that usually land the candidate of first choice do sacrifice some democracy and some transparency.  It is risky, particularly at this time, to allow too many people who have no training in basic board governance to have input and a role in the search process.   

 All committee members have private agendas at some level as each seeks a trait or experience in a new head that reflects his or her own definition of the school’s mission. However, some members may have an inappropriate motive such as wanting to hire a head who might fix a narrow parental based issue. They may become blind to candidates’ other qualities that do not fit with their agendas. 

When emotions and stress levels are high, there is a chance that some degree of objectivity will be lost. For example, the faculty and parents may overly push for an educational leader who can “fix” remote learning while some board members may be focused upon finding a head with a strong track record in turning around enrollment or the bottom line. 

All searches result in an unhappy outcome if the board does not have an effective chair and a well-trained board who understand and apply the principles of good practice. Trustees who speak out of turn, gossip, criticize the previous head or exhibit micromanaging behavior send the message that they are an unprofessional board that would scare any head.

Boundaries and channels must be observed at all times. There can be no side bar conversations between the search committee and other constituent groups, including other board members, unless a formal structure of advisory committees is set up and the rules for their communication with the candidates and the search committee are very clear and followed explicitly. Advisory committees provide feedback only; they do not vote.

Search Communications

In any head of school search, it is important to strike the appropriate balance between too much and too little information.  Now more than ever, however, constituents have “a need to know”. Periodic updates on the progress of the search are important. These can be posted on a separate section of the school’s website devoted to the search.

It is always crucial to protect the confidentiality of outside candidates whose current boards do not know that they are pursuing alternatives. During this time, semi-finalists and finalists may have limited exposure to constituents. That is no reason to abandon caution in respecting candidates’ confidentiality; failure to do so will mar the school’s reputation in the independent school world. 

Respect Inside Candidates and the Departing Head

One of the first challenges facing many a search is how to deal with internal candidates. Some search committees believe it is wise to ask one or more insiders to throw their hat into the ring. The old adage “the devil you know is better than the devil you don’t” has some merit, and inside candidates have the added advantage of needing relatively little time to adjust to their new role while outsiders need at least three years to do so.

Sometimes, however, insiders may have little or no realistic chance of success. Why? The “warts” of the insider are only too well-known and boards seem to want “fresh blood” not afraid of instituting change and upsetting the school culture. A risk to the school is that if the insider’s candidacy is destined to fail, the school will be left to manage that individual’s disappointment and disgruntlement. In the worst case, the bypassed insider could undercut the new head with teachers or parents.

On the other hand, one School had a strong Assistant Head who had been waiting in the wings for some time. This Consultant conducted focus groups with a cross-section of key constituents on school climate and quickly reached the conclusion that this individual was highly respected and would be embraced widely as the new Head of School. The wise Board moved quickly to appoint him. He has enjoyed a relatively seamless transition; he has a healthy relationship with the Board; he is executing the mission according to the strategic plan; AND the School saved all of the expense of a full-blown search. This is a time when internal candidates deserve a very serious look.

Under no circumstances, is it wise to appoint the inside candidate as an interim or acting head. That will drive away savvy, qualified outside candidates who view the insider as having an unfair advantage.

“The king is dead” refers to the departing head. While departing heads usually know their proper place in the search process, they are understandably concerned about their legacy and may be anxious about the next career move. Treat them professionally and with gratitude and respect assuming that the separation did not result from egregious behavior. Plan a celebration of their accomplishments. Invite them back to the school occasionally for very important events.

Remember that the new head will be watching how the departing head is treated as a sign of the treatment that he or she can expect to receive.

Manage the Candidate Pool and the Compensation Package

The search firm should be ranking prospective candidates, providing the search committee with a complete dossier of the candidates’ credentials and references and encouraging them to interview the most attractive candidates via Skype or Zoom as soon as these meetings can be scheduled. This can be difficult during this time, but the search committee must stay on track.  Dragging out the process is detrimental not only to the school but to the candidates who need to keep all of their own options in play. 

At all times, a good search firm manages expectations because the “ideal” candidate possessing ALL of the characteristics needed and/or desired in a new leader probably does not exist. The candidate pool is a fluid mix: leading contenders may drop out or unexpectedly disappoint, or a young, ambitious senior administrator may seem like a breath of fresh air and take everyone by surprise. One of the roles of the search consultant is to keep the committee open to and excited by the changing candidate mix and to create interest on the part of heads who may not necessarily be in the market. It is important to keep the pool viable and not let the search committee become too excited too early about a single candidate.

Search committees tend to recommend, and boards choose, a replacement who is often the polar opposite personality and style of the predecessor. Normally, the longer the previous head was in place, the more opposite is the personality of the successor. This pendulum swing can be averted by the guidance of a search firm that understands typical patterns of behavior of search committees and encourages a balanced outlook.

In an external search, it is imperative that three to five candidates remain engaged in the semifinalist stage and two finalists be kept in the loop until the first-choice person agrees formally. On the other hand, continuing to look too long for the “right” candidate may lead to an aborted search AND misleading a candidate to the extent that he or she jeopardizes his or her current position gives the school a bad name

Once the new head has been chosen, the compensation decision is an opportunity to build upon goodwill.  This happens IF a search consultant with experience in the independent school world has knowledge of the various components of a compensation package. The firm informs the search committee in advance what it may take to land the candidate of its choice. Littleford & Associates works for the boards of schools either when the firm is engaged as the search consultant, or when the firm is retained only at the closing compensation phase.

Aside from an intimate understanding of school culture and history and board and faculty politics, the search consultant needs an in-depth knowledge of all of the following: the candidate’s current compensation package; overall financial health and family circumstances; the financial condition of the school; total compensation paid to the current head; the attitude of the board towards compensation and its willingness to be flexible and creative. 

Only one person, usually the search committee or board chair, works with the consultant in negotiating the package to be offered to the finalist. The search consultant needs to know the “hot buttons” or “deal breakers” for both parties, and their respective negotiating styles.

Sometimes the finalist raises the ante by asking for pay or benefits that were not on the table as part of the initial compensation conversation with the search consultant or the search chair. These could be totally fair OR the requests could indicate a future pattern of behavior of the head conveying one sentiment and then changing course unexpectedly. The chair may grant these requests in order to close the deal, but an underlying resentment may linger, and the new head may be under more pressure to perform.

Selling Your School

Search and advisory committees tend to want to grill the candidates and forget that a key element of the search process is selling your school to them.  The typical search timeline includes onsite visits that give the candidates multiple opportunities to observe all aspects of the school in action.  At least this fall when many searches are entering the final phase, semi-finalists and finalists will not have the same chance to view the obvious (students, faculty, staff and faculty interacting in and out of the classroom) and assess the subtleties (school climate and morale, faculty and staff dynamics, parent-faculty relations and the board relationship  with constituents). 

Search committees have to work even harder to make their sales pitch and to assuage candidates’ doubts about what they are missing by setting up Zoom focus groups where physical meetings are not possible. The search consultant should provide assistance in setting up these meetings in order to give the candidates as much information as possible.

The Transition

This Consultant has written extensively about the fact that the transition period for a first-hand head or an experienced head in a new school is as important, or even more important than the search itself. During the pandemic, heads may not have the luxury of a honeymoon, and they may not have as many opportunities to build the critical political capital that they need to survive beyond three to five years. Boards are going to have to step up and help them build that reservoir of good will more than ever.

For more articles on this important topic of transition please visit our website

Littleford & Associates conducts full searches worldwide; has a proven process for vetting internal candidates; facilitates head compensation contracts for new and existing heads of school; and provides expert guidance in head of school transition. Please contact for assistance to heads of school and boards.