Being a Head of School
What was the hardest thing that you needed to learn in your first year as a head?
Amy Wasser: The areas I had the least experience in were budget and development. I spent a lot of time with our business manager and the board treasurer learning about accounting practices, what reports were expected when and the purpose of each one. How to build a budget, and why we needed a zero balance budget, was important; it was important to me that the board understood that I did not have experience in this area and that they needed to support my ability to learn and to have patience as I did.
I also needed to become more confident in the role of fundraiser. When I began as head of school, we did not have a development director, and many of the direct asks fell to me, along with the oversight of stewardship. I went to workshops and forced myself to be confident in my ability to speak about the school to donors and make the ask!
Ilisa Cappell: Every new head faces challenging moments. From those early experiences, I learned that I needed to pause and reflect on what my difficult feelings were teaching me so that I could learn from them and strengthen myself in my leadership. Those emotions were not a sign something was wrong or that I was not the right person for the job; rather, they signaled that something I cared about was at stake.
I learned early on that strong lay-head partnerships are at the core of strong schools. I needed to prioritize developing relationships and partnering with the board. My board comprised a group of wonderful people and they too were learning and evolving as a board. Many of them were also parents in the school. I had to invest time and energy in working with them to develop partnerships and healthy governance practices.
I learned to share about areas in which I needed support (finance and budgeting, fundraising) so that I could acquire the skills I needed to do my job well. I found that being vulnerable with my board about both the highlighs of my work and areas of challenge provided them with the opportunities to support me in the ways I needed to be successful in the role.
What were the kinds of challenges that you felt made the job especially difficult?
Amy Wasser: For me, it was my place in the community. I had been at the school on faculty for six years when I became interim head and then head; I was a rabbi’s wife, parent in the school and young enough for many of the faculty to be my parent. I had to prove myself as a leader and find the balance for all of my roles so that I was seen as the head of school, while not losing the importance of those other hats I wore. For sure, I had to remove myself from my kids’ day-to-day actions at the school and always remind teachers that they were not to get any special treatment. (My kids told me I was harder on them than anyone else!)
I expected it to be hard to work with the parents, but other than the rare occasion, that was not the case. In those instances, it was hard when I felt I had to support a parent over a teacher (because I genuinely felt they were in the right), and it was also very hard when a parent would not respect a teacher as a professional and felt they knew better.
Ilisa Cappell: I carried a heavy emotional load because I cared so much about the teachers, the students, the parents and the community and about making what I perceived to be “the right decisions.” I understand now that sometimes the issues we were navigating were so complex that it wasn’t about making the “right” decision - It was about making decisions that were aligned with our values, about doing the best with the data we had at the moment.
Living and working in the same community felt really challenging at times. As an introverted person who held a public communal leadership position, I needed to learn to develop a sustaining approach to my work.
There is a tension between the head’s role in managing up to the board and the board being the ones who hire/fire the head of school. I learned that the board wanted support in developing its own leadership practices, and that I had the opportunity and resources to build relationships with the board to help them become more effective in their role. At the same time, I was always acutely aware that I was the sole employee of the board, and that in order to get the feedback I needed to be successful in my role, I had to work with the board to develop a Head of School Support and Evaluation Committee; share leading practices in this area and help strengthen their capacity to provide the oversight, feedback and support I needed to flourish in the role.
Where did you find support, both inside your school community and beyond?
Amy Wasser: This was an area of weakness for me, as I did not do a good job of asking for outside support. In hindsight, I am not sure I knew I could or what was available. Being in a smaller community, I was not that well connected in the day school world (that changed over time), and I did not know about coaching, mentors, etc.
I did get involved in our local independent school network and had some strong relationships with my fellow heads in Tampa. Because I had been on faculty, I had a good relationship with the team at school and was able to continue to build those connections. I also leaned on my admissions director, the only other full-time administrator at the time, and she was a true partner.
Ilisa Cappell: I became a part of DSLTI as I started my tenure as head of school. The support of my colleagues and mentors, coupled with the opportunity to learn about content specific to the role of head of school influenced my practice tremendously. At the time, I was also a part of (then) RAVSAK’s Reshet community. I accessed PEJE’s resources and grants for heads in transition and in specific areas like admissions, development and governance. I felt a part of something larger than myself and connected to a community of leaders whom I knew I could count on.
I worked with a coach and developed strong mentors who cared deeply about me, and provided me with space to reflect on my practice and who cared deeply about me. I cannot stress enough the impact having a coach in my corner had on my practice.
Faith and the recognition of this work as being in service of Hashem and the Jewish community remain at the core of my "why"- for engaging in this work. I felt closest to our mission when I was with the children, and I felt blessed to have the chance to spend time with our children each day.
Tell us about a time when you didn't see how you would manage. What enabled you to pull through?
Amy Wasser: My most difficult situations revolved around board issues. I think such a challenge for school professional leaders is having a new board chair every 2-3 years, together with their peers. When they understand good governance, it works, but when that is not in place and the lay leaders are serving for the wrong reasons, it can be a very hard and lonely place for a head.
For the most part, there were always one or two wise voices that helped to bring change, and those folks were a very meaningful support for me. Unfortunately, I endured two very public lawsuits while I was HOS; both were personal injury cases where the injury happened on campus and both went to trial. Very very stressful and not an experience I wish on any HOS; I will say the leadership was very supportive during this very hard time, twice.
Ilisa Cappell: I was the head of a small school and we were the only Jewish day school in the community. A family came to us wanting a Jewish education for their child who was on the Autism spectrum. I believe so deeply in an inclusive Jewish community and Jewish education and wanted to build a school where all children could thrive. It felt challenging to figure out how to balance what felt like our responsibility as Jews and as educators with the needs of this child, the other children in the school, and our staff who worked tirelessly to meet a range of learners in their classrooms with limited resources.
It was also hard to manage the different perspectives on this issue and work with people whose views differed so much from my own. It helped me to be clear on the values guiding our choices, to access to resources and support from other school leaders who had navigated similar terrain, and to seek wise counsel from an incredible team of teachers (distributed leadership team) and communal leaders. Recognizing that I was operating in a complex framework for which there was no simple solution helped me to see the system in new ways. This clarity helped me to navigate the situation.
What do you want to tell current leaders that you wish you had known when you were a head?
Amy Wasser: Get a coach; connect with other day school heads; visit more schools; know your strengths and do not be afraid to ask for help with what you do not know how to do; create a small peer to peer group for yourself; make good choices for your own professional development; don't implement too many changes at once in the program, it takes a few years to really make change last and make a difference and faculty can only adapt to a few changes at once; you do not have to hop on every bandwagon; make good choices for changes in the school; care for your staff and model that in how you care for yourself.
Ilisa Cappell: Leading schools is infinitely more complex now than it was when I began my tenure as a head of school. Investing time in developing school cultures that are psychologically safe and accountable is a core component of the head's job. Work tirelessly to ensure this is true of your school culture, and you will have created conditions where your team can thrive.
Emotional literacy and self-awareness are critical leadership dispositions that need to be nurtured and developed. At any moment, you can learn from the difficult and joyous feelings that arise daily in your practice. This learning can enable you to become more effective in your role and help you more readily support your team.
Resiliency is not about how much you can endure, but about how well you can rest and recharge.
Effective feedback is a game-changer. It has the capacity to help transform our practice when we are part of a community that prioritizes learning. I wish I had invested more time in normalizing and practicing giving feedback and having difficult conversations with my team and with my board.
Never underestimate the power of listening deeply and being present with the people around you.
Being a Board Chair
In your time as a board chair, what was the biggest difficulty that you witnessed for the head being able to fulfill his or her role?
Elissa Maier: Navigating competing demands and leaning into the role as the school executive stand out for me as being some of the more complex challenges our heads of school faced. Leading the educational direction of the school came more naturally; however, the work in leading the operational management of the school required learning new and different skills. This included getting comfortable with fundraising, making hard decisions about financial priorities and navigating the lay/professional relationships in working with a board.
Cheryl Rosenberg: Our head of school had two challenges. One was a founders’ board who were used to rolling up their sleeves and doing the work of the staff (because they had to in the beginning). Transitioning the board members out of these roles so that the head could properly manage operations with his professional staff was challenging, and many relationships were damaged and had to be repaired. The other challenge, disguised as a blessing, was a school that was growing so quickly that the administrative and operational structures could not keep up. The school went from 150 kids to 500 in three years, and the structures and personnel had to be put in place to properly manage the new reality.
Describe one or two ways that, in your personal interactions, you ensured that the head felt supported?
Elissa Maier: One of the most important ways I found to support the head was to actively listen. It was so important to allow the space for the head to share their thoughts, reactions and ideas and for them to know that our conversations were a safe place to share openly and honestly. After addressing an issue and coming to an agreed-upon solution, we always stood united as a team. We could safely agree and disagree when we worked through questions, but when we presented externally, we were always a united front.
Cheryl Rosenberg: I believe that support is often felt most when it is demonstrated both publicly and privately. For me, this often looked like keeping difficult conversations and disagreements on issues private while publicly supporting the head with both my words and actions in every situation. If a head can trust the board chair to support them publicly in all instances–with parents, staff and the board–they feel as though they have a true partner so that they are not alone in solving problems that arise.
How did you work with the rest of the board to support the head?
Elissa Maier: As someone who was knowledgeable and experienced in the role of board and best practices in governance, I prioritized the need to improve our governance practices. I worked to improve our board planning and implemented systems to ensure more effective meetings. Simple changes such as creating timed meeting agendas and sharing necessary information in advance of the meeting made a critical difference. One of the most important committees I established was a Committee on Trustees to ensure a strong succession of leaders.
Clarity of roles and responsibilities was also key to our successful working relationship. At the beginning of my tenure, we discussed our leadership roles, agreed to how and when we wanted to communicate and articulated the things that were important to each of us to ensure a strong partnership. Having clearly articulated roles and effective communication helped us to work together successfully.
Cheryl Rosenberg: During my term as president, I established the school’s first ever head support committee, and he was able to choose the members. This allowed us to do two things: first, it gave the head of school an “insider circle” to talk to that he could trust to keep things confidential and understand his perspective; second, when there were board concerns, it allowed the board members a way and a timeline to give feedback so that it could be passed along to the head of school by the committee, eliminating board members reaching out directly to the head of school with negative feedback.
Was there one time or incident you can talk about where you made the most difference in the head's work?
Elissa Maier: I implemented a strong process for evaluation and feedback, and I think it made a significant difference. I put together a process where we gathered feedback from administrators, teachers, parents and board members. After sharing the feedback, together we developed goals for both individual growth and goals for the school. We held ourselves accountable to reviewing achievement of these goals, and this process provided a clear plan for the year. By having clearly articulated goals, we were able to work in partnership towards the achievement of these goals.
Cheryl Rosenberg: I feel very strongly about the role of the board in fundraising - that every member should give and get, and that each board member must make the school one of their top three charitable donations. I personally asked each board member for their gifts and their time in making asks, which was something the head of school historically spent a whole year working through. This allowed the head of school to focus on those asks only he could make, as well as to increase his focus on non-fundraising matters.
Were there times when you felt overwhelmed by the stress and volume of work as a board chair, and if so, how did you care for yourself?
Elissa Maier: I was fortunate to have the support and guidance of a great group of distinguished school leaders. I was able to convene and seek guidance from prior chairs of the school and seek their insights in guiding some of our more difficult decisions.
I also had a strong executive committee, whose members were my thought partners and who shared in the leadership responsibilities. My successor was identified as I began my term as president and thus was able to serve as a partner and had the opportunity to learn and prepare for her leadership role.
Cheryl Rosenberg: The times when I felt most stressed were during periods where I felt like as board members we were only privy to the challenges of running a school. During those times, it was easy to forget all of the incredible, inspiring things happening every day to transform children’s lives. I implemented a structure to ensure every board meeting started with a presentation on something positive and powerful happening in the school, and I also made it a point to frequently be present in the school for special occasions - like Maccabiah or Hallel - which nourished my soul and gave me the energy to continue the important work.