The Head of School Conundrum: A 21st Century Leadership Challenge

By Dr. Chaim Y. Botwinick

Over the past several decades there have been a plethora of articles, papers and research regarding the new and evolving role of the Head of School as “instructional leader.” This reality takes place against an ever expanding landscape of schools which are faced with the difficult and often perplexing challenge of identifying, recruiting and retaining the “best and the brightest” talent to “lead” their schools into the 21st century.

In 2010, an article in Kappa Magazine, entitled “New Thinking about Instructional Leadership,” authors Eileen Horng and Susanna Loeb posited that “schools that improve student achievement are more likely to have principals who are strong organizational managers than are schools with principals who spend more of their time observing classrooms or directly coaching teachers.” This hypothesis is based upon an expanding body of research which challenges our understanding regarding the traditional role of the Head of School as being totally occupied with the hands-on day-to-day teaching and learning activity in the classroom. To be sure, according to Horng and Loeb, “the quality of teaching in a school, in many cases, can be affected only marginally by a principal’s involvement in the classroom.”

Whether or not one agrees with this hypothesis, one thing is clear – today’s Head of School must spend less time focusing on “hands-on” “in-the-trenches” classroom learning, instruction and curricula at the expense of spending more time as a forward thinking inspiring leader, strategic thinker, change agent, motivator/influencer and vision-driven innovator. By doing so, it will enable the Head of School to focus on other critically essential components such as Board recruitment, retention and development, financial resource development, developing school-wide standards and benchmarks, teacher recruitment and retention, admissions and community development – to name a few.

The Head of School who micro-manages his/her school, is by definition, caught-up in organizational minutia, weeds and trees as opposed to focusing on the forest. He/she focuses more on the train schedule rather than on the train cargo. As a dear colleague once stated: “you can’t always fret about when the train arrives and leaves the station (you should empower other folks to worry about that) unless you know the train’s destination; and, that your passengers are on the right train and are safe.” This is just another way of paraphrasing Jim Collins who posits that effective and successful organizations need the right people in the right seats on the bus going in the right direction. This is not to suggest that the instructional leader disengage him/herself from the wonderful spell-bounding magic taking place in the classroom or from the power of the teacher-student learning process or student achievement – three of the most critical components of effective schooling. What it does suggest however is a challenge and opportunity for the Head of School to merge and blend the leader and manager domains comfortably, seamlessly and effectively … and, by doing so help create and foster a school culture which is effective, viable, resilient, meaningful and sustainable.

Heads of Schools today are naturally faced with a myriad of ever increasing complex challenges, exacerbated by limited resources, greater calls for accountability and transparency, institutional competition, and demands for greater educational quality assurance. They are required to lead and manage vertically and horizontally and at the same time build capacity and an operational infrastructure and systems as well as an educational culture for effective education service delivery. This also assumes that our Heads of School are appropriately trained, experienced, skilled and well-prepared to take on these monumental and at times daunting tasks and responsibilities.

As we well know, today, the Head of School is by-and-large challenged to inspire and lead more so than ever before; and, not limit their energies to teaching teachers how to teach. In order to do so, they must learn how to hire, lead and manage staff, empower faculty and delegate to those school personnel who are trained to assume greater responsibility with authority and accountability. More often than not, Heads of School fall prey to micromanaging their respective faculty and staff due to a variety of factors – ranging from a lack of confidence in their respective staff to their own individual insecurities or just plain inexperience. Leading and directing organizations effectively requires experience, exposure and skill. It also requires big picture strategic thinking and tremendous self-confidence, maturity, modesty, trust, authentic vulnerability and a willingness to take balanced and measured risks, anchored in model educational practice. This is not to say that there are a growing cadre of outstanding school leaders who are exemplars of best practice and who are continuously at the top of their leadership game. These successes are due in large measure to the amazing impact of institutions of higher learning on school leadership practice, more sophisticated and sustained professional development programs, greater access to high quality mentors and coaches, hands-on experience in the field, and a greater awareness and consciousness regarding leadership expectations, transparency and accountability.

In the final analysis, leading and managing schools effectively should not be mutually exclusive. Several ways in which the Head of School can merge and blend leadership and management skills include, but are not be limited to the following repertoire of beliefs, practices and behaviors:

  • Ensuring that all policy, educational and administrative decision-making processes are data driven, and not based on political expediency, just an item on a check-list, or for personal gain;
  • Offering ongoing constructive, reflective, sensitive and often-times difficult feedback to administrative staff and faculty anchored in best practice;
  • Providing administrative staff and faculty with well-defined opportunities for professional growth, development and reflection;
  • Making faculty meetings learning opportunities (remember, all administrative stuff can go into emails; no need to eat-up precious staff/faculty time to review lunch orders, PE or carpool schedules);
  • Ensuring that the school’s curriculum is always aligned with the school’s core values, mission and vision (assuming they are well articulated);
  • Ensuring that all faculty, staff and board agendas are “action focused” – otherwise, why meet; reports can be committed to paper and read – why waste precious time?
  • Make conversations with faculty and staff more about them and the school – not about the challenges facing the Head of School;
  • Find time to engage in personal and professional reflection;
  • If feasible, engage a coach in order to help counsel and guide you;
  • Be concerned about the quality of your time on task – is your time being well spent, directed or utilized effectively? It’s not about time-on-task, but the quality of time-on- task;
  • Exhibit and demonstrate Jewish role-modeling;
  • Always be transparent;
  • Don’t use too many clichés or overly-quote management/leadership gurus, buzz words or catch-phrases – they get stale really fast;
  • Always begin meetings with a Jewish value or inspiring words of Torah in order to set the stage for a meaningful dialogue and conversation;
  • Hire and engage administrative staff who you can delegate to; otherwise, why are they at your school?
  • Do not expect reciprocal trust on the part of your faculty and staff until you have exhibited trustworthiness on a consistent basis.

The following is a summary of twenty (20) deep-dive guiding “power principles” for effective Head of School leadership. They are intended to help inform and guide the manner in which Heads of Schools can evolve, develop and grow as true inspiring leaders, role models and exemplars of leadership excellence.

  1. Always strive to delegate and empower others, utilizing the strengths of your team members; channel and direct their strengths;
  2. You don’t need to have all the answers; or be the expert in everything; if you don’t have the right answers, seek them out from others who may;
  3. Always seek advice and authentic feedback from your staff and faculty;
  4. Hold everyone, including yourself accountable;
  5. Exhibit Derech Eretz, empathy and compassion for your students, staff, faculty and parents;
  6. Be passionate about your job;
  7. The school’s core values, mission and vision is your road map and compass, use them wisely and strategically;
  8. Take risks, but ensure your decisions are well-informed and data driven;
  9. Trust is earned not acquired – it should never be transactional;
  10. Admit mistakes, but don’t overly apologize or misdirect the blame (never play the blame-game);
  11. Give credit where credit is due – always seek ways to celebrate your faculty and staff;
  12. Keep your Board of Directors informed continuously – no surprises;
  13. Always keep your team motivated;
  14. Act decisively – procrastination will paralyze;
  15. Build leadership in others;
  16. Think and act strategically;
  17. Develop your own professional goals in partnership with your Board of Directors and always manage Board expectations;
  18. Articulate your vision with clarity and conviction;
  19. Don’t mistake “sizzle for stake” – it’s not about charisma, it’s about substance; and
  20. Enjoy your leadership role and responsibilities – “positivity” can be extremely rewarding, contagious and motivating.

The aforementioned check-list of Head of School leadership principles, qualities and attributes can very easily be applied to any senior level leadership profession. Our challenge however, is to apply them directly to our leadership roles in Jewish day school education, by first recognizing their importance, relevance and application. Only then will we be in a more credible position to celebrate and embrace Jewish day school leadership excellence – a sine qua non for effective Jewish schooling.

At the end of the day, Heads of Schools will always be required to navigate crises, exigencies, problems and pressures of the 21st century Jewish day school. They will be judged not necessarily by the number of fires extinguished, speeches or pronouncements made or crises averted, but rather by the manner in which they were able to direct, channel and lead their schools to ensure high levels of educational standards of excellence and above all, measurable student achievement, progress and success.

Dr. Chaim Y. Botwinick has enjoyed a variety of senior leadership positions in Jewish education including Principal of Jewish Day Schools, CEO for Central Agencies for Jewish Education and senior educational consultant to Jewish Day Schools and Jewish communal institutions. He is the author of “Think Excellence: Harnessing Your Power to Succeed Beyond Greatness” (Brown Books, 2011) and has lectured extensively throughout the United States and Israel.