On Shabbat mornings in many synagogues, just before we prepare to return the Torah to the ark, we recite a blessing for our community and leaders that celebrates some of the specific roles that our leaders play–providing lamps for illumination, wine for kiddush and havdalah, bread for guests, charity for the poor. In this prayer, we acknowledge that even acts such as keeping the lights on matter. Those who tend to communal needs merit our communal supplication for God’s support and protection. Our collective hope in reciting this prayer at this moment is to single out the people who provide services for the general good, to amplify the role of those who help facilitate Torah learning and inspire others to emulate their behaviors. Through these words, we acknowledge that the leadership of those in our community merits our collective energy, focus and blessing.

In this issue of Kaleidoscope, we have the opportunity to hear from leaders of our Jewish day schools and yeshivot. We thank these leaders for their vulnerability in sharing their experiences so that together as a community, we can learn more about what we can do to support, sustain and nourish our professionals in their roles. We are grateful for our ongoing partnership with DSLTI: Day School Leadership Training Institute and for their dedication to building and sustaining current and future heads of school. The conversation they convened at the Prizmah Conference in Denver about head of school sustainability served as a catalyst for this critical issue.

Carrying the weight of leadership in a Jewish day school is an enormous task. Through reading about the experiences of these heads, we gain a deeper understanding of our leaders, what our schools need to thrive, and what we can do to share the load and carry this sacred responsibility together.

The Critical Importance of the Head-Board Relationship

The work of a head of school is high-stakes. The job of head of school has expanded over the years; what used to be a primarily administrative role now includes financial management, fundraising, relationship-building, not to mention navigating pressure from various stakeholders and serving as a role model and hashkafic or ideological fit for the school and community. 

Some have likened the role to that of a college president. Heads need to possess a high level of self-awareness and commitment to the emotional side of the job, which usually takes an unseen toll. They need to know how to pace themselves, how to lead up to get support from their board. Heads need to stand in deep relationship with their board members in order to serve the school successfully.

Prizmah unpacked the dynamics and determinative nature of the relationship between lay leaders and heads of school in research published in 2020. These findings, as well as data from the broader independent school world, underscore the power of the relationship between heads and their boards. Prizmah’s work with hundreds of schools and leaders and our contributions to the head search processes at dozens of schools in recent years provides a clear perspective on the challenges inherent to the Jewish day school talent pipeline.

We know that the sustainability of heads is directly correlated with the strength of the relationship between lay leaders and heads and the efficacy of their boards. We believe strongly (and the research supports) that this relationship is a powerful lever—among others such as access to strong professional networks, coaching and mentoring, quality professional development and distributed leadership teams—to drive stronger schools and longer tenures for their heads.

Why does this matter so much? 

Through data and on-the-ground observation, we’re seeing just how difficult the endeavor of headship is, and how much the head’s wellbeing impacts the entire school community. The head bears responsibility for all the individuals in the school community–in all their beautiful complexity–and for the health of the institution, heaped with the mountain of expectations/responsibility/hopes/projections of so many. These are very hard roles to fill.

Supporting the head matters so much. First, it is our collective responsibility to protect our leaders as human beings. We must remember that they are people with families and feelings of their own. Second, heads of school are vital for ensuring student success. Effective heads help maintain a positive school climate and advocate for the school in the community. Their approach to recruiting faculty, financial management and strategic planning impacts, even in indirect ways, on the learning environment in the school. Lastly, the cost of head of school turnover for schools and communities is high, in financial terms as well as in the time and emotional energy that is a part of any search process.

The question of turnover itself requires deep consideration. Many board members recognize their responsibility to “hire and fire.” However “hiring and firing” (or, more optimistically, “hiring and honoring those retiring”) is meant to happen only periodically. The bulk of the ongoing job of board members should be about identifying ways they can strengthen the school through the current head’s leadership, not fantasizing over an imaginary better candidate. This is all the more important at a time when the talent pipeline is precarious and unpredictable. To be sure, not all turnover is bad. New leaders can bring a new vision and energize a school community, but instability in schools impacts everyone.

How can we make a difference?

No matter what role you play in a school community, you have the ability to support your school’s leadership and increase the likelihood that your head will actually thrive. Board members can especially influence a head’s ability to serve with success.

There is a critical power dynamic inherent in the board-head relationship. While the head is the only one in a position to manage up to the board directly, the head is also the only employee of the board. This dynamic is complicated by the reality that heads generally live in the same community as their school’s board members and share personal and social connections. Board members must be vigilant about their own competing priorities and mindful of their commitment to confidentiality, especially when they have children in the school and organic relationships with other school professionals and lay leaders. The same warmth and “heimishness” for which schools are famous can sometimes prevent the leadership, both lay and professional, from leaning in to hard conversations or difficult decisions. 

Board members can become more aware of this dynamic and more self-aware of their own leadership and help heads carry the weight in very specific ways. First, they can help the head to prioritize clear goals. There should be multiple opportunities throughout the year for board members to check in with their head through a support and evaluation committee. As unanticipated needs emerge and demand attention, the head can rely on board members for focus and support in prioritizing shifting needs. Second, board members can make it a practice to communicate directly with the head. Support does not mean exclusively cheerleading but instead involves clear and constructive feedback designed for growth. By investing in its own growth and demonstrating a willingness to be steadfast and strong in the face of changing priorities, the board stands beside the head. Finally, the board can understand and create space for the head to talk about vision.

Correspondingly, there are ways heads can articulate their own needs, manage up and help the board to be a strong partner. Heads can learn about what effective board function looks like and work to strengthen their board’s governance and leadership practices. Heads can communicate about areas in which they feel uncertain and seek feedback and support from all directions. This can be particularly challenging for brand new heads who are transitioning into the role. When a head needs to say no to some things, inevitably, the emotional weight of these decisions can feel heavy, especially decisions of great consequence related to admissions or hiring, for example.

What can be done right away?

Changing mindsets and long-established habits does not happen overnight. There are ways to make incremental progress in creating a headship model that is more sustainable. Prizmah’s workshop on what it means to be board chair is a great way for those new to the role to get off on the right foot. Similarly, Prizmah partnered with DSLTI to launch a cohort for new heads of school, including sessions for new heads and board chairs to work on alignment and setting norms for their working partnership. We have an upcoming series on collaboration through controversy that is designed to strengthen lay-head partnership and outlines how to set a foundation for success. Schools can think more seriously about the notion of sabbaticals, and the day school field can explore what apprenticeship models might look like for up-and-coming leaders. 

The board can play a critical role in ensuring the holistic wellbeing of heads, not merely job success. Research shows that leaders who thrive are ones who are provided with ongoing professional support (coaching/mentoring), spaces for open and honest discourse with people who understand the inherent challenges and opportunities of the role (new heads cohort group/other professional groups), and guidance if they are relocating to a new town, including support for their own family, ensuring that the head of school’s spouse and children, if applicable, have what they need. 

Developing a greater sense of empathy and understanding for what it takes to be a Jewish educational leader might help more leaders feel seen and understood and ultimately enable them to be more effective in their roles. It might also lead more young people to consider and commit to careers as school leaders. We want people to want the job as head of school, to stay in this job and to feel good about the job. 

Ultimately, our schools are our community’s biggest investment in our collective future. When all members hold a share of that enormous responsibility, we protect our investment and honor the vulnerability of those who will ensure its payoff.

I am no expert on sustainable headship, at least in terms of years. I began my tenure in July 2020, so I’m just getting ready to sign my second contract. But considering the intensity of my first couple of years (I count them in dog years), I had to quickly develop survival strategies. 

Sustaining my school, my team, my family and myself through that time was the hardest work I have ever done. That early experience helped me recognize the many levels on which the headship could yield a fight or flight response. Purely by necessity, I set out to build a sustainable system to survive the early years of my leadership—with the hopes of moving from survival into “thrival” mode in the next few years.

One of the most challenging parts of the role that can come as a surprise is the psychological weight that heads carry. The workload is heavy, the inbox always seems to refill, and the number of meetings packed into a day (or night) boggles the mind. But most people who are used to hard work are up for those challenges. It’s the mental load—the sense of ultimate responsibility—that weighs so heavily and, to my mind, accounts for the short tenure of most heads.

My approach to this has been an amplification of my general philosophy, which is to work with and hire extraordinary people and to truly empower and support them. Coming into a new workplace and culture mid-crisis made it challenging to demonstrate my commitment to empowerment at all levels of the organization, but it means that I can now more clearly articulate what needs to be true for this leadership approach to work. 
I believe there are at least four key elements to its success.

Shared Vision

First, there needs to be a shared vision between the head of school and members of her leadership team. I don’t mean that the head shares the vision and everyone listens, nods and takes notes. Rather, the vision needs to be shared on an elemental level—in our bones and kishkes—that develops organically through deep relationships and a shared orientation and philosophy. 

To be clear, this is about big picture vision, not the granular. In fact, if the head has a very detailed and exact picture of what they need their school and program to look like, this can be a major impediment. When you have a shared big vision, that still allows for many smaller choices and directions—but the leader has to be comfortable with any of those outcomes to have a truly empowered team.

Shared Standards of Excellence

The shared vision must be accompanied by shared standards and expectations of excellence. If you are aligned philosophically but not qualitatively, struggles and frustrations will develop on that front. Unlike shared vision, which is more innate or organic, these standards can be formulated and workshopped as long as the head and team have the ambition and stamina to consistently meet them. 

In order to authentically develop these communal norms and expectations, early on the head has to be prepared to allow some (lower stakes) things to not meet the highest expectations of excellence. Those programs can then be used to calmly reflect—with an individual or a team—on why they did not rise to the level they should have. The team will learn more and more quickly by doing, and falling short a few times, than by being told exactly how to execute every step of a perfect event. To be explicit, a leader of an empowered team cannot be punitive or angry about such low-grade missteps; it’s part of the deal.

Delegation vs. Empowerment

Intentionally allowing small mistakes requires the leader to exercise restraint strategically early on, not to always step in to fix and not to get upset if things don’t go perfectly. This is one of the many short-term vs. long-term trade-offs leaders need to make every day. A misstep in the short-term must be seen as an opportunity for reflective practice and growth, and for the evolution of shared standards of excellence in the long-term. It’s worth it! 

If heads can’t restrain themselves from intervening in everything and being punitive about mistakes, they run the risk of creating a culture of delegation, which is dramatically different from empowerment. With delegation, the leader continues to be accountable for every detail, even if they aren’t executing them. This has two major downsides. First, the team members don’t feel empowered, which is a hit to their sense of growth and trust (and therefore retention) in the workplace. Second, to my mind, delegation is also a major source of the mental load that so many leaders carry, and moving away from it is one of the keys to sustainable leadership. Trust your team—which shares a vision and high expectations—to figure out the details in their area of expertise.

Seeking Support

Knowing that your team members know when to seek support is a critical element of an empowerment culture. The leader can only comfortably and confidently let their team members fly if they know they won’t be shy about seeking advice and backing, or sharing when things aren’t going well. We all need that support, and being vulnerable enough to visibly model seeking it (from mentors, board members, and the team) communicates that this too is an essential part of the supported empowerment model. 

I try to live and lead authentically by this approach each day. Honestly, it’s the only way I know how to work and get the job done. To be fully transparent—and so my team doesn’t giggle behind my back about the exception that proves the rule—I simply cannot yet fully empower when it comes to the food we serve to our staff. This may come from being a vegetarian at one too many kosher events, being morally opposed to mayonnaise-based meals, or recognizing that this is a crucial way we can show appreciation to our team during tough times. In any case, I own (and joke about) that this this is a place where I struggle to hew to my own approach; I think it’s important that we know and share our empowerment weak spots. 

My plan now is to judge my own sustainability in this job not by the number of years served, but by the number of meals served—without my controlling the menu.