Navigating the Jewish Day School Leadership Matrix

By Dr. Chaim Y. Botwinick

Over the past several decades, the Jewish Day School community has experienced a wide array of cutting-edge professional leadership development milestones. These included (to name a few), the creation of exciting leadership recruitment programs and retention practices; the provision of university-based and communally/foundation-sponsored leadership training institutes; the design and implementation of serious mentoring and coaching interventions; and, the effective use and application of reflective leadership performance assessments.

A review of impact data (empirical and anecdotal) suggests that many of these leadership initiatives have enhanced the effectiveness of Heads of School and Principals. They have also helped create a communal environment and culture which supports, promotes and celebrates professional leadership excellence, and, its impact on institutional effectiveness.

By-and-large, most of these leadership initiatives (depending upon community), are complemented by impressive compensation packages to levels never before imaginable. To be sure, the current salaries, benefits, and retirement packages for many Heads of School and Principals, compared to a decade ago, are now extremely competitive. Not unlike other professions in the nonprofit world today, the competitive nature of these compensation levels have given rise to other evolving challenges and opportunities – including greater demand for higher levels of executive leadership performance, impact and accountability.

As we paint a portrait of the 21st century professional Jewish Day school leader, what emerges is a profession which has recently experienced and enjoyed significant visibility, stature and growth. This reality is evidenced irrespective of the relatively high turnover rate of day school Heads of School, when compared to their leadership counterparts in other private and public schools.

There are volumes published detailing the factors attributed to this turnover phenomenon. Some of the factors may include, but are not limited to; desirability of a specific geographic location, number of years in the field, job satisfaction (or dissatisfaction), Board-Head of School relationships, career advancement and leadership effectiveness. Other factors may be attributed to a lack of a clear and concise understanding regarding differentiated roles and responsibilities of the head of school and school trustees; lack of a shared vision regarding the school’s philosophy and direction; and a very rudimentary understanding regarding Head of School performance goals and expectations.

Although one can argue that these factors exist in virtually every senior nonprofit leadership or management position, there is a very unique and distinctive leadership matrix which Jewish day school heads must navigate and negotiate in order to succeed, let alone thrive and grow. As a Jewish day school trustee once quipped at a recent major day school leadership Seminar which I had the pleasure to facilitate – “today’s Head of School is no longer viewed exclusively as a senior instructional leader, but rather as a super-manager of a highly complex eco-system called school.”

He continued…. “true inspirational day school leaders must multitask, manage and successfully exhibit a host of multifaceted challenges ranging from the effective supervision of senior level staff to managing complex marketing and fundraising initiatives; from board development to curriculum design; and, from strategic planning to budgeting and plant operation.” In addition, to succeed, the Head of School must continuously inspire and respond effectively to the needs of multiple “consumers” simultaneously, namely, students, teachers, administrators, staff, parents, board members and communal leadership. A tall task indeed!

This description of responsibilities, as presented by the trustee, was not intended to be an exaggeration or sarcastic in nature, but rather as a sincere, honest and deep-felt understanding and perception regarding what the trustee perceived as the true role of a Head of School.

After hearing (and writing down) this statement as well as witnessing the reaction of all those in the room who actually agreed whole-heartedly with this statement (more lay leaders than professionals), I reflected long and hard with the question – where is this misguided and misinformed perspective coming from? What other profession today really and truly expects its senior executive to actually possess high levels of expertise in each of these critical areas? Surrounding yourself with a high impact school management team of professionals who possess these skill-sets is an imperative. But, to expect the head of school to singularly exhibit proficiency in each of these areas is overly ambitious and unrealistic to say the least. Furthermore, any head of school who actually purports to possess all of these areas of expertise or skill-sets needs a reality-check and must reevaluate his/her dependability, reliability and credibility.

So, why would a Board member (and maybe even other lay leadership), truly expect a well-respected, credentialed, experienced and highly trained Head of School to actually succeed in each of these areas of specialization? Moreover, is it truly fair or even appropriate to assess head of school’s performance, impact or effectiveness in these range of disparate specialized areas?

In order to begin to respond to these daunting challenges, one needs to examine more closely how Jewish Day Schools recruit and hire new school heads; and, how/why candidates apply for these these challenging and demanding positions.

Over the past ten years, I have had the pleasure and privilege to coach a cadre of senior executives of nonprofits and heads of Jewish Day schools. The number one challenge most School Heads share with me, almost without exception, is their inability to respond effectively to and/or keep pace with the increased demand, volume, pressure and magnitude of new unexpected or unanticipated demands and responsibilities outside of their expertise, delegated by the Board. This is particularly challenging when the demands are not in concert with a Head of School’s leadership skill-set. This is not about intellectual bandwidth, grit, potential or the ability to be nimble. Nor is it about motivation or capacity. At the end of the day, it’s about high performance skill-set and experience – plain and simple.

In order to succeed in today’s ever-demanding field, Heads of School must possess grit, flexibility, resiliency, and above all expertise. Anything less than these attributes creates an environment that does not advance the institution and more often than not, creates a level of acrimony which can actually place the senior professional in executive jeopardy.

So, in order to understand how this leadership matrix impacts on Head of School effectiveness, a deeper-dive into the complex dynamics of Head of School recruitment and selection process are in order.

Although this may sound like a generalization, more often than not, Head of School job descriptions include the standard and normative (textbook/boiler-plate) listing of leadership roles, characteristics, responsibilities and best practice requirements; and, most candidates will interview for these positions with tremendous confidence – convincing Boards (and themselves) that they are the best candidate to do the job effectively…. even if select skills are not within the candidates “comfort zone.”

This reality, and the need for candidates to put their “best foot forward” and “impress’/convince interviewers that they are the best fit for the job, is normal. But at times, it does create false Board expectations; and, challenges the capacity, bandwidth and ability for the Head of School to eventually carry-out the multitude of complex assignments and responsibilities, irrespective of the candidate’s lack of experience or expertise.

As an example, the most common challenge for many a Heads of School is when the candidate is asked by the Board (after being hired for only six months on the job) to engage in activities such as fundraising, board development, strategic planning or any other activity which was not listed at the top of the job description pyramid. As we know, fundraising, board development and strategic planning are painfully time-consuming, and require high levels of executive skill, experience and expertise. More often than not, the Head of School will undertake these assignments at the expense of other instructional leadership responsibilities. And more often than not, as we know, what happens when the Head of School abruptly leaves his/her “comfort zone.” It usually leads to failure, frustration, conflict and at times, dissonance. Having said that, fortunate is the Head of School who can assemble an effective Management Team with expertise in these specialized areas of expertise.

So why and how do Heads of School become mired-down in these circumstances? How and why do they happen with such frequency? What are the consequences when they happen? And, what measures can be taken in order to prevent them from happening at best, or minimizing their impact when they do happen.

Clarity, Honesty and Transparency:

In order to more fully understand the nature and scope of this phenomenon, we must begin with “the end in mind.” This means that it is imperative for senior executive search committees to not only clearly articulate job responsibilities, but it is essential that the board prioritize these responsibilities and skills prior to meeting with candidates. By doing so, job expectations and corresponding executive skill-sets and expected outcomes are clear, concise, realistic and shared. It also puts the candidate on notice that “honesty is the best policy.” No matter how passionate, ambitious or desperate the candidate is (for the job), the candidate should never ever suggest (in an interview) that he/she has experience, expertise or skills-set in areas which they don’t. It will catch up with the HoS sooner than later…. honesty is the best policy. The same holds true for the search committee. No matter how desperate this search committee is to fill this important leadership post, the committee must take its time and engage in due-diligence in order to ensure the best fit for the position. Not second best, but the best!

Finally, it’s equally important for the Head of School search committee to carefully vet the candidate’s references and to listen very carefully to what references are saying and, are not saying about the candidate. The committee must ask the hard and difficult questions regarding the candidate’s skills. All too often, search committees get caught up in a candidate’s style, optics and demeanor, but compromise on critically important concrete executive skill-sets and areas of expertise. This is a mistake. And it usually catches up with the committee (and head of school) within the first 12-15 months of the Head of School’s tenure.

Several Suggestions:

In order to help respond to many of these challenges, the following is an inventory of Dos and Donts – as they relate to the search committee and head of school candidate respectively.


  • All job responsibilities must be clear, concise and understood by the school’s search committee, school board of directors and head of school candidate;
  • Responsibilities or duties that are vague or unclear, must be either clarified or eliminated;
  • The committee and board of directors must determine which five (5) executive skills-sets represent the top priority areas in order of importance;
  • Performance benchmarks, goals and job expectations must be clearly indicated and articulated during the interview process;
  • The search committee must share with the candidate how and when the candidate’s 360 performance review will be conducted and assessed. To this end, a head of school performance review committee (“PRC”) must be established for this purpose;
  • The “PRC” must meet with the head of school throughout the school year in order to provide the school head with ongoing support and performance feedback;
  • The results of a 360 performance review must result in an agreed upon professional development action plan;
  • The search committee should make a determination regarding the short, mid and long-range skills which are absolutely essential to the candidate’s current and future success, effectiveness and impact;
  • The candidate must be up-front and candid about his/her executive skill-set strengths and weaknesses;
  • Head of school search committees are in search of candidates who will “lead.” The candidate must provide concrete examples as to how he/she will lead the institution into the future. Case examples must be requested;
  • The school board must ensure that the head of school candidate, once hired, is provided with the necessary resources in order to success;
  • It is wise to have two people co-chair the search process, in the event one of the co-chairs cannot maintain the leadership position as co-chair; momentum is critical;


  • Never hire a candidate until the search committee completes the interviewing process with all potential candidates;
  • Never hire a candidate if there are doubts about the candidate’s background, expertise, skill-sets or fit for the job (no compromising);
  • The search consultant sees the total school, not the individual candidate, as the primary candidate;
  • If the school engages a consultant to assist in the search, every effort must be made to understand the school – its mission, its culture, its tolerance for change, its preferred leadership style, and the nature of the position to be filled;
  • The search committee must never just settle for a candidate. It must be energized by the possibility of engaging its next professional leader of the school. In the final analysis, whomever is hired will be a reflection on the search committee and board;
  • The search committee process must begin early in the year in order to ensure sufficient time for the search and engagement process to take hold;
  • The candidate should never oversell or over-market his or her executive skills;
  • All search committee deliberations must be confidential;
  • Never discuss or negotiate compensation packages with the candidate until after the position is actually offered to the candidate; and,
  • Make sure that the candidate finalist has ample time to ask probing questions relating to the position.


The purpose of this post was not intended to reinvent the Head of School recruitment wheel, nor was it intended to provide readers with out-of-the-box recruitment ideas. The purpose rather was plain and simple – to emphasis the critical importance of developing a systemic and planful approach to head of school recruitment protocols and requirements, against a backdrop of complex institutional and leadership challenges.

More often than not, in our passion and zeal to fill Head of School vacancies, search committees jump into the recruitment fray with little regard for best practices, processes or methods. This results in a series of compromises which eventually impact negatively on desired outcomes. More time and energy spent on the front-end of these processes and procedures prevents back-tracking or having to pivot down the road when a Head of School issue arises.

This reality also holds true for the manner in which a head of school candidate prepares for and engages in these search processes. Know your strengths; know your weaknesses and be transparent. And, above all, please never make it up as you go along. The field is plagued and beleaguered with Heads of School who are in jeopardy due primarily to their inability to navigate the ever-complex executive management “web” entitled the Head of School “Leadership Matrix.

Dr. Chaim Y. Botwinick is currently Principal of the Hebrew Academy Community Day School, Margate FL, organizational consultant and executive coach. He is the founding partner of LEV Consulting Associates and specializes in leadership development and strategic planning. He served in a variety of senior Jewish educational leadership positions on the local and national levels. Dr. Botwinick is the author of “Think Excellence,” Brown Books, 2011.