The scene is familiar to all of us who work in schools—small groups huddle around tables in breakout spaces; printed drafts travel around the circle, gathering comments in their margins, improving as they move from one hand to another. Now and then, someone looks up and asks the group a question. They talk for a while, considering that question and others that flow from it. Heads bow over the papers again, more notes and more questions, then suddenly the time is up. Everyone packs up and ambles into the hallway, finishing conversations, crossing paths, and speculating about next steps. But this particular scene is not depicting groups of middle or high school girls working on a presentation for English or biology class. Instead, the groups in this scene are Castilleja School (CA) trustees collaborating with members of the school’s leadership team to create the next strategic plan. It’s not surprising to see the teaching and learning experiences on campus so closely mirrored in our strategic planning process. Our mission at Castilleja—to educate motivated young women to become confident thinkers and compassionate leaders with a sense of purpose to effect change in the world—ensures that collaborative work is a constant not just at every grade level, but across all areas of the school. Independent school leaders nationwide are increasingly aware that in a rapidly changing world, the nature of strategic planning is changing as well. When big-picture thinking is happening all the time in different settings, the strategic plan takes on a new vital role—organizing concurrent ongoing initiatives into a cohesive vision. This shift means the planning process can become organic not only to the school itself but also to the particular moment in the history of any school. The Learning and Leading Framework At Castilleja, we now recognize that strategic planning is an iterative and ongoing process, not simply a once-every-five-years stand-alone task. For example, our 2013 plan had actually been written as an update to the plan we wrote in 2008, which had been more far-reaching and innovative. So by the time we began in August 2018 to define the scope and purpose of Castilleja’s next strategic plan, we knew it would be less about generating new goals than it was an opportunity to align the ongoing strategic work underway. I remember being keenly aware that our process would be, as we often say in education, as important as our product, because the plan would need to effectively integrate all the ongoing initiatives and changes we were already considering. Our community, our program, and our campus master plan are always in the spotlight, for example, so our new plan would need to reflect the evolving visions and community-wide goals already emerging in each of these arenas. While the strength of our mission provides clear direction and vision for Castilleja, our motto—Women Leading, Women Learning—reminds our community that compassionate leadership is a learning process. Our students mature as leaders by developing specific competencies, including curiosity, purposeful reflection, and empathy. As leaders of the school, the board chair and I are always discussing these concepts in relation to our shared work, which has shaped our relationship as one characterized by respect and collaboration. By the time we began this planning process, our board chair was entering into his fourth year in the role. With three years of weekly meetings behind us, we were strong partners working to build the best possible future for Castilleja. Together we form what I have come to see as one corner of a balanced leadership triangle. The board of trustees, comprised of current and past parents, alumnae, and local thought leaders, forms the second corner. The final corner is our leadership team, a group that includes administrators, division heads, program directors, deans, and department heads. The strength of this structure enables us to have daily strategic conversations that became the foundation of our plan. With this balanced leadership framework in place, we established the scope and purpose of our plan. We set out to align and integrate our ongoing work, while also taking the time to examine our vision more comprehensively in the context of our understanding of future opportunities and constraints. To co-chair our efforts, we first tapped the trustee who we hoped would become the next board chair, leveraging this opportunity to begin leading while creating the plan. Assuming that she did become chair, she would be uniquely poised to execute the plan moving forward. We selected as her partner a trustee who had recently led the strategic planning process as board chair at another school, hoping that we could all learn from his valuable experience. Once these co-chairs were in place, they plunged directly into the work, understanding we hoped to complete the plan within a year. We committed to a timeline that would give us ample time to coalesce, while ensuring the act of “planning” did not take away more time than needed from the more relevant task of “doing” the important work ahead. The timeframe was ambitious, but in the independent school world, the future really is now. Voice and Choice Teachers at Castilleja are focused on the role of voice and choice for the next generation of women leaders. This commitment to expanding options for our students shapes the architecture for our proposed campus modernization and forms the foundation of our latest additions to the course catalog. So it is no surprise that voice and choice also became key elements of our strategic planning process. With a strong committee in place and an established timeframe, our next decision—whether to engage outside consultants to oversee the process or to shepherd the plan to completion relying on internal resources—was at its core a question of voice and choice. What role would our community play in the process? Where did our voices belong, and which choices did we want to drive? At the outset, it seemed like a tall order to complete the plan quickly and entirely on our own, but it also began to seem like the most logical path forward. As a school, we are always thinking and learning about the factors that will shape the future. We consistently explore the state of women in the world, the impact of global politics and the economy, new findings in brain research, and issues and movements related to social justice. This outward-facing and forward-thinking perspective means we are regularly bringing new lenses to how we assess our program and how we innovate to make it more relevant. Ideologically, we were prepared for the work ahead without needing additional expertise to broaden our horizons. Practically speaking, we were prepared as well; the balanced leadership triangle we had in place included trustees who had vast organizational expertise, creative drive, and strategic vision. I had been Castilleja’s assistant head and then head of school through two previous strategic planning processes and was entering my 20th year at the school. Our leadership team brought deep subject-matter expertise and personal investment in the key points that external consultants would need time to learn. Did we have that time to spare? Perhaps even more important, did we want to engage in a top-down process where the board partnered with consultants, or could an on-the-ground internal process lead to more authentic, achievable, and relevant goals? As we weighed these questions, we also acknowledged the powerful momentum of three major initiatives already underway on our campus—our application to the city of Palo Alto for permission to modernize the campus and increase enrollment, our continued evolution away from Advanced Placement classes to Advanced Topics courses guided by interdisciplinary content areas, and our desire to broaden our social-emotional learning programs to redefine success and further support student well-being. All three of these important efforts created a complex landscape, for sure, but they were also initiatives that we had nourished and nurtured for years, converging at this particular moment in the history of the school. If we understood that voice and choice were crucial to our students’ growth, we also knew that we had a parallel opportunity to develop and strengthen Castilleja by completing the work from within—a plan by and for Castilleja. On one level, this outcome was obvious to everyone involved. On another level, it was an act of faith. On yet another level still, it was an investment of many resources. Our trustees have always been generous with their time and talent, but the members of the planning committee deepened their commitment, and our leadership team added to their already-full schedules to dive into this new undertaking. At this point, the broader decision to trust our voices to plan internally carried forward into one other choice that distinguished our process. In the past, much of the critical work our consultants had done was to put together representatives from various constituencies to weigh in about different initiatives at the outset. This time, we decided, that because we had opted to trust our expertise, we wanted to apply that knowledge right away. In partnership with the strategic planning co-chairs, the board chair and I put together planning subcommittees based on the teams that had been working together on these various goals since their inception. Together these subcommittees spent hours in small group meetings, more hours reading and revising to create goals and resolve debates, and then even more hours soliciting and integrating input from our constituents all along the way. In the final phase, members from our communications department joined the process, working closely with the co-chairs to incorporate feedback and bring the project to completion. It was consuming and compelling work that grew in relevance and reach over the course of the year. The Value of Generative Work and Active Listening In the traditional system of checks and balances that characterizes independent school leadership, the board of trustees usually concerns itself with questions of why an institution values particular goals, and the administration addresses how those goals are achieved. The work that took place around those tables in the breakout spaces brought the why and how of Castilleja into direct conversation—which, as it turns out, improved our questions, our answers, and our goals. It was not a straightforward or easy path. After all, there are good reasons that why and how do not always sit down at the same table. When they finally do, however, if they can emerge with confidence and compassion and a sense of purpose, constructive dialogue leads to shared learning. When the co-chairs and leadership team presented the working drafts to small groups of teachers for the first time, even with the early input they had provided, their questions came so quickly it was hard to capture them all. Teaching and learning is passionate work and does not coalesce quickly into a series of tidy goals. Our co-chairs began carefully adapting the language of the plan so that the broader vision they had articulated would reflect what they learned from teachers about the intentional work they do in classrooms every day. Gathering feedback about the working drafts from groups of parents and students took place during several open meetings, and the resulting questions and concerns were incorporated into the overarching series of goals for the future of the school. The sessions also yielded one unexpected benefit: Several of the newer parents who participated brought expertise and passion that was valuable to other school initiatives and committees. This internal planning process created an opportunity for our next generation of parent leaders to step into the conversation. We teach active listening in every setting at Castilleja—in our classrooms, in advisories, in community outreach programs, on the athletic fields—and as leaders, we honed these skills ourselves, taking every voice into account and revising our drafts with a clearer perspective and fresh eyes. Our process was iterative, interactive, and instructive. Even after so many years at Castilleja, developing this strategic plan taught me new lessons about the school community I know so well. It also reminded our leadership team and board of the lasting value of sitting down around the table, putting our heads together, and doing the work. The results are two-fold: a plan that is true to our community and a partnership among the leaders who will take responsibility for achieving the goals. Relationships As educators, we know that every good project begins with a strong set of teaching objectives supported by clear lesson plans. Strategic planning is a project like any other, and part of our success with this endeavor rests on the same framework. At the outset, we chose to structure our plan around four foundational pillars that support, represent, and inspire our community rather than frame it as questions or statements as we’d seen in many other strategic plans, including our own from the past. Each was drafted by a mix of trustees and administrators working together. This choice was driven by a desire to define our vision using the clearest, most elemental terms possible to organize our goals. Over the course of the year, the names of those pillars and what they represented evolved, but ultimately, we landed on School Community, encompassing the people at Castilleja—the students, employees, alumnae, and past and current families; Student Experience, defining our teaching and learning; Beyond the Circle, addressing Castilleja’s role in the city of Palo Alto, in the realm of all-girls education, and in the world as an advocate for equity and women’s leadership; and Resources, focusing on the fiscal strength and goals now and into the future. As we listened and revised many times over, there was one sentence that resonated in every room and never changed once over the course of the entire year: “Relationships are at the heart of Castilleja.” Even though it introduced our School Community pillar, we discovered that it supported all of the other pillars as well. This realization gave an even sharper focus to our vision for the next five years and marked something of a sea change for Castilleja. Our past strategic plans had always led with a section about the academic program first, and it had seemed fitting that this one would as well. However, as this observation about relationships developed into a thesis, the co-chairs, the board chair, and I sat together in my office and quietly reorganized Castilleja’s strategic plan to lead with School Community. We did not need to check in to be sure of the choice; we had listened closely all along. Castilleja’s program, impact in the world, and resources for the future all stem from the relationships we nurture. It was a paradigm shift, a bold path forward, and a true story. While it might be possible to tally both the paid and volunteer hours that went into the plan our board unanimously approved on Sept. 9, 2019 at 10 a.m., that accounting would never convey the true value of the generative work our board, leadership team, and greater school community engaged in together. Although we knew that this process was an opportunity to align and empower our goals into a cohesive vision, we could never have predicted the extent to which it would also align our community in ardent support of that vision.