Dr. Chaim Y. Botwinick
August 17, 2026
In my former capacity as head of school, principal and now executive coach and day school
consultant, I am often asked to describe the characteristics of an outstanding or exemplary
head of school or day school principal.
Although there are a wide variety of responses to this important query, the answer is not a
“one-size fits all”.
More often than not, our Jewish day school and yeshiva community confuse management
skills with leadership skills. But demonstrated exemplary leadership goes far beyond the
limitation of only ensuring that the trains are “running on time”.
Being an exemplary day school or yeshiva educational leader requires a skill set which
transcends scholarship, knowledge, experience or expertise. Although these attributes and
characteristics are essential, exemplary leadership also demands a mindset, personality,
demeanor and insight into human nature and a sensitivity which transcends the need to
embrace empathy, middot tovot and menchlichkeit.
Definition:
Head of school excellence is an executive leadership responsibility for establishing,
monitoring and scaling the highest academic and operational standards across one or
multiple campuses.
As opposed to focusing only on daily administrative details like a traditional principal, this
role centers on broad strategic developments, curricular frameworks and alignment, data-
driven student performance and the professional coaching of teachers.
Today, the head of school plays a critical role in driving school excellence by serving as the
primary visionary, cultural leader, and strategic anchor of an educational institution.
Achieving excellence as a head of school requires balancing community engagement, staff
empowerment and the establishment of rigorous academic norms and standards.
Head of School Leadership Characteristics
Instead of managing just the day-to-day logistics of a single building, the head of school
focuses on macro-level strategic planning, cultivating a uniform culture of peak
performance and standardizing best practices.
In addition, the exemplary head of school creates and fosters a healthy community culture
and manages strategic operations to ensure that students and teachers and staff reach their
fullest potential.
The “Four Pillars”
There are essentially four “pillars” of school leadership excellence.
They include: strategic alignment, community engagement, holistic support systems and
collaborative teaching teams.
In addition, the top attributes of exceptional school leaders are radical transparency –
fostering an atmosphere of trust by keeping families, staff and students actively informed;
data-informed guidance by using student achievement and performance metrics to
differential teacher support and eliminate localized learning barriers; people investment
by cultivating leadership pathways for staff through focused mentoring and targeted
professional development; and embracing fallibility by demonstrating humility through
learning openly from mistakes in order to model resilience for the students.
The Jewish Component of Exemplary School Leadership
When identifying the Jewish characteristics of exemplary school leadership, there are
several significant attributes which are very evident.
They include displaying middot tovot, developing and implementing policy decisions which
are embedded and anchored in Jewish values and dass torah, modeling value-based
behavior as Torah observance individuals, acting in accordance with Kiddush HaShem and
modeling derech eretz to students, parents, teachers and members of the community.
In addition, exemplary Jewish school leaders engage in their own Torah learning
obligations and scholarship in order to help inform others understand and appreciate the
profound centrality and critical importance of Torah study, learning and scholarship.
Finally, expressions of love, passion and affinity for eretz yisrael, medinat yisrael and am
yisrael are critical dimensions of a head of school’s role and value proposition.
As we know, head of school leadership from a Jewish perspective is deeply anchored in
service, humility, modesty, and moral responsibility rather than autocratic power. As such,
the professional Jewish school leader acts as an empowering teacher and as a servant of the
community.
When directing a day school or yeshiva, the exemplary leader views and demonstrates the
highest form of leadership. This requires helping faculty and students see, think and adapt
in new ways rather than issuing top down directives or commands.
The Empowerment Model
One of the most critical attributes of a high performing head of school is recognizing that no
one person can lead alone and that sharing responsibility with other staff and faculty and
actively mentoring and training others to lead becomes paramount.
Empowering teachers transforms them from mere instructors into autonomous leaders
who deeply impact student academic, social and emotion growth and success. True
empowerment therefore requires shifting from rigid, top down control to a school culture
of deep trust, professional respect and shared decision-making.
This “empowerment model” also guarantees that there is leadership continuity and
sustainability and helps ensure leadership succession in the event the head of school
moves on. Finally, it offers faculty and staff the opportunity to share in the success, growth
and development of the school through real-time hands-on leadership responsibility and
obligations.
Identifying, Creating and Sustaining Exemplary School Leadership
As indicated, educational leadership does not happen in a vacuum. As such, every Jewish
day school or yeshiva Board endeavors to identify and hire the most outstanding person to
lead their school. But, as we know, reality dictates that this is not always feasible. To be
sure, professional day school and yeshiva leaders are just not sitting around ready to be
engaged or hired. They are in all probability already engaged by a school and are
committed to their positions.
Engaging Leadership
The characteristics and attributes of exemplary school leadership as just indicated may
appear to be simple and straightforward. This may be true. But it does not necessarily
suggest that there are a pool of such leaders just ready and willing to be hired and engaged.
There are essentially three approaches (and possibly more) in order to identify and engage
exemplary day school and yeshiva leaders.
One approach is by conducting an extensive and comprehensive search. The other
approach is by engaging the current head of school in a comprehensive and extensive in-
service coaching and training program. The third approach, which is usually the most
common, is to search for a new head of school with the understanding that he/she will
require extensive coaching, mentor and guidance in specifics areas.
The slight advantage in pursuing the third approach is that the professional is already
somewhat familiar with the culture of the school. This reduces the learning curve and
hopefully, the training experience.
A Word of Advice and Caution
Every day school and yeshiva wants to hire and engage the most qualified and outstanding
person for the job.
Searching and engaging for a day school and yeshiva head of school is always challenging at
best. It can be extremely stressful for the school faculty, board and school community; or, it
can be a surprisingly smooth straightforward process.
Critical to the success of this challenge is for the school search process to identify those
leadership characteristics and attributes that represent the highest priority for the school.
Once this leadership baseline is established, the search process takes on a new, exciting and
important dimension. By the same token, if a school does not engage in this process,
educational excellence and exemplary school leadership will be very difficult if not
impossible to achieve.
Finally, the day school and yeshiva that continuously and passionately strives for
educational excellence and exemplary chinuch will in all probability achieve it over a period
of time.
This institutional aspiration will however require high levels of motivation, laser-sharp
insight, a clear vision and unswerving perseverance. But above all, it requires a willingness
to accept failure, learn from that failure and then immediately move forward to succeed.
Friends….remember, there are very few if any excellent day schools that are lead by poor or
mediocre leaders. But, there are many poor institutions that are led by less than average
leaders who lack leadership skills.
This differentiation should be obvious and straight-forward.
About the Author:
Dr. Chaim Botwinick is an organizational consultant and senior executive coach. He served as
president and CEO of the central agency for Jewish education in Baltimore and Miami and as
head of school and principal for a variety of Jewish day schools and yeshivot. As an Influencer
in education, Dr. Botwinick has lectured published extensively on topics relating to strategic
planning, leadership development and school change. He is the co-founder of LEV Consulting
Associates and the producer and host for the Chinuch Horizons podcast series. Dr. Botwinick is
the author of Think Excellence, Books, 2011.
