Valuing the Profound Power of Continuity in Headship

Summer 2022

By Dan Glass

NAIS-4-FINAL-NEW-copy.pngThis article appeared as "Deep Impact” in the Summer 2022 issue of Independent School.
When I came to The Brandeis School of San Francisco (CA) as a 35-year-old, first-time head, I said my aspiration was to retire from this headship. I’d seen the positive impact of longevity in the head role at independent schools near me—Reveta Bowers at The Center for Early Education, Mark Salkind at The Urban School, and Al Adams at Lick-Wilmerding, to name just a few—and it struck me that there is profound power in such continuity.
I was recently talking about the value of leadership continuity with a supporter in our broader community. She had asked about my takeaways from leading a school through the pandemic—especially anything that might have resonance beyond schools. By the time the pandemic hit, I explained, our leadership team had largely been working together for more than five years. We were able to anticipate challenges amid change and plan accordingly. That has enabled us to achieve stronger metrics across the board, from parent and faculty engagement to increased giving, enrollment, and stronger financials. I also shared with her how I suspect, in our ongoing orientation toward innovation as an industry, that we may dismiss too quickly the positive gains from a group working together over time (and I will say, as a lifelong Warriors fan, I see this year’s team having such success as another example of the impact of teaming over time).
I’ve seen the tumult at peer schools when heads come and go, and it is hard not to appreciate the steadiness of lasting leadership. The difference in clarity that Brandeis has achieved in years of ongoing conversation and shared work is stark; it stands to reason that the positive impact of sustained tenure would amplify over time. The connections I’ve built as a head of school—whether sitting with the kindergartners in morning meetings or with faculty members at a funeral—deepen, as do all healthy relationships, over time. There is certainly value that accrues to the school, and to the person in the headship, by investing in those relationships for the long run.
Seven years into my role, I remain steadfast in my thinking that this will be my permanent professional home. Recently, I was asked what it would take to make that goal a reality: What are the conditions that would make it possible for me to last long term in this headship, given the volatility of the position? The first thing that came to mind is “We Shall Not Be Moved,” the civil rights movement song and fixture of my Berkeley childhood, whose biblical refrain asserts that “like a tree planted by the water, we shall not be moved.” The song harkens back to Psalm 1:

Blessed is the person…who delights in and meditates on the law of the Lord. They will be like a tree planted by the rivers of water, bringing forth fruit in season; their leaves will not wither, and their works will prosper.
The psalm is certainly a vision of sustained success and growth. But what would that look like in the context of school leadership? Recognizing that I am an imperfect observer, being early yet on this path, I’ve come to three reflections that speak to my ability to stay rooted here at Brandeis—and to the value of leadership continuity.

Get Planted

When I was a candidate for headship, I frequently received advice that I should find a school that I could fall in love with because I would need to love a school to lead it. It’s good advice, yes, but it’s surface-level advice. The work isn’t in the falling but in the sustaining. Perhaps better advice for leaders aspiring to longer-term positions in schools might be, find a school you want to marry.
And what does that search for a life partner look like? You want to be sure your values are aligned, of course, as are your goals. In my search for a headship, I knew I was seeking a spiritually supportive school, one that was intellectually invested in teaching as an art form and committed to the well-being of its students, faculty, and families. And this relationship wouldn’t be mine alone: The questions my family and I considered extended beyond the walls of the school. We knew we wanted to be in the San Francisco Bay Area, to raise our daughters near cousins and grandparents, and we sought an urban community, where our family’s diversity of spiritual backgrounds would be welcome and our love of the arts would find fertile ground. We measured our conversations with community members by their authenticity, trying to imagine developing meaningful partnerships and lasting friendships.
You want to find waters that will enrich and deepen your roots, for those days when you will be buffeted by the world. For my family, that was about loved ones and friends, community, museums, and music. For others, it might be about languages, the great outdoors, or a spouse’s career. Whatever the set of variables are for you individually, in addition to truly loving the school, keeping them in mind as you plant yourself with intention will serve you well. We are in control of far less in our lives than any of us likely imagined.

Delight and Meditate

There is a prayer in Jewish practice traditionally said when studying Torah, and, in common practice, it can be used for any sort of study. Its meaning, in essence, is what a blessing it is to busy oneself with learning. Despite my broad religious education and strongly affiliated family life, this prayer was not part of our routines or rituals. I learned it for the first time when sitting down with a trustee and rabbi to study Mussar—a medieval Jewish mindfulness practice, also new to me in coming to Brandeis. Leaning over a table in my office, together we walked through the Hebrew, and the rabbi explained her own practice of dedicating learning to someone in the world in need of healing or strength. So we blessed the learning we would do and thought of those in our lives who could use a little help.
This anecdote illustrates what I believe to be a particularly critical condition for longevity in the headship: that the head of school role be a space of ongoing learning of a sort that will nourish the spirit as well as the mind. I have known heads who lean heavily into aspects of their school’s mission, becoming experts in single-sex education or public intellectuals touting assessment reform. I have also known those who look beyond the mission of their school to develop as lifelong learners—folks who have pursued certifications in coaching, mindfulness, or facilitation. 
Certainly, the headship offers tremendous opportunity for growth. Few heads take on the role knowing everything from land use law and HR compliance to best practices in playground design or major giving programs—or global pandemics. And there is plenty in the day-to-day life of school leadership that creates space for true delight—spend a few minutes with second graders puzzling through the interpersonal challenges of group work to be reminded of the preciousness of any given moment in school. 
But I would argue that there is an additional aspect of learning for the long-tenured leader, one that speaks to the soul. In one of my favorite poems, “The Idea of Order at Key West,” Wallace Stevens notes how the lights of fishing boats at anchor have the effect of “Arranging, deepening, enchanting night.” So too, I believe, this kind of delighted and meditative learning, a learning that enriches the spirit, has the capacity to deepen and enchant our work in the world, and our leadership in schools. For me it has been about Jewish identity, text, and history, and the fascinating unfinished project of Jewish education in America. Finding a school that encourages you to be such a learner is as important an element of longevity as any.

Recognize the Seasons

In the first leadership team retreat I held as head at Brandeis, we worked with school leadership consultant Debbie Freed to do a deep dive into our school’s history and culture. Over the course of an afternoon, this team—some of whom are still here, some of whom left in short order—created a massive timeline of the school, stretching back over unrolled butcher paper to its founding in 1963 and forward to its present, with a new head, new mission statement, and new name. Several of the team members at that time had been at the school for more than 15 years; one was in his fourth decade as a teacher and administrator. Among all of us, we tried to name the various inflection points across the decades—new campuses built or signature programs launched, new leaders hired, mergers with other schools as well as conscious uncouplings. We scribbled notes attached to dates, footnotes attached to notes, and questions in the margins. 
For years, I kept the scroll of paper in an office closet. What was I to do with all that history? I did my best to honor it, seeing myself as a holder of the school’s stories, dusting off the binders of typed board meeting minutes from the 1960s or visiting a university library to sift through the papers of a founding rabbi. As I lived into my own present with the school, that timeline rolled up in the closet began to undulate in my mind, and I began to imagine its hash marks not as numbers in a sequence but as moments in a cycle, a sine wave, a measure of cyclicality. 
Schools are seasonal communities, and those of us who love schools often love them for their cycles of turn and return. We attend to the crisp beginnings in fall and the brightness of the days as spring bends toward summer. We cherish the pauses along the way and the rituals we come back to year after year.
To imagine a leadership trajectory that stretches across decades is, I believe, to understand those decades in cyclical, seasonal terms. A season to reap, and one to sow. These were the years of our founding and growth; these, the years when we expanded our reach; in these years we turned our focus inward, creating a foundation of academic excellence; these were years marked by strife on the board. Perhaps these cycles align with external factors, like strategic plans or accreditation visits or with aspirational projects like new capital campaigns and facilities. Perhaps they are the seasons of a particular person or group’s tenure: beloved teachers and colleagues or an especially philanthropic family or strong trustee leader. But in all cases, the work is to understand the school to be in a state of becoming, perpetually, rather than a predetermined telos, a drive toward a singular end.

A Moment Like This

These broad ideals pale in comparison to the day-to-day importance of a supportive board and a team that inspires and trusts one another. And surely there is a great deal of privilege embedded in my (white, cisgendered, straight, male) ability to choose a place of work. I recognize, too, the degree to which the assumption that I would be worthy to fill this office over time is itself a prideful one; the decision about whether a head is the right fit for a school is a collective one and not the single jurisdiction of any individual.
I find myself thinking of my Jewish grandmother’s inclination to cross her arms and spit three times to ward off the evil eye, as I dare to imagine a healthy or successful or anything-other-than-precarious future. The poet in me sees hubris in each sentence, and we all know what pride goes before. Still, there is something profound in saying yes to the opportunity to reflect on what I love about my job, and what I hope will sustain the relationship I have with this special school over time. And I hope these notes from a stop along the road to longevity are useful to other heads or aspiring heads out there as you consider your own journeys. 
Dan Glass

Dan Glass is head of school at The Brandeis School of San Francisco in California.