Ilisa believes that inspired, informed, and supported Jewish day school leaders are the key to healthy schools. As the Senior Vice President, Engagement at Prizmah, Ilisa works to help sustain and advance Jewish day school leadership through coaching and through serving as the director of YOU Lead, Prizmah’s signature leadership development program. Ilisa is a former head of school, an alumna of Cohort 4 of DSLTI (Day School Leadership Training Institute), and a sought after leadership coach with over 18 years of experience in Jewish education. She is a graduate of Barnard College of Columbia University and holds a master’s in Jewish education from the Jewish Theological Seminary. Ilisa earned her certificate of nonprofit board consulting from BoardSource and consults regularly with schools on governance. She is certified in The Leadership Circle Profile™ and earned a certificate in leadership coaching from Georgetown University. Ilisa is also an Associate Certified Coach (ACC) and member of the International Coaching Federation (ICF). Ilisa is deeply committed to developing strong lay-head partnerships and creating conditions in schools where leaders can thrive.

Sharing a Sacred Responsibility

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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.