What keeps independent school leaders up at night? If you ask any school head or other school administrator this question and attempt to unpack it, what becomes immediately clear is that it is actually much more complex than a singular question. Are we seeing a new recognition of the urgency for fundamental school change? Are we pushing our thinking as hard as we must in order to adjust to the really big changes in the world? Are leaders focused on the urgent or the important? Are we trapped by our individual and collective experiences of the last few decades? What questions should we be asking that we are not? And, perhaps most importantly, what can we learn and leverage when school leaders step aside from their role as “chief of everything” to their even more critical role, asking “is our future strong and sustainable?” In an attempt to provide a window into the collective mindset of school leaders, I gathered some data, along with John Gulla, executive director of the E.E. Ford Foundation, during a workshop at the 2017 NAIS Annual Conference. We asked the audience of about 100, mostly heads of school, four big questions and gathered their short responses on Post-it Notes. I conducted similar sessions at other workshop events with heads and trustees of the Virginia Association of Independent Schools, Northwest Association of Independent Schools, The Association of Boarding Schools, and at several individual school board retreats. At all these sessions, I used the same prompts to get into the minds of school leaders: What is it in our organization and structures as independent schools that make it challenging to pursue a longer-term vision for the future (e.g., comfort with the familiar, inertia or success, head turnover, board term limits, annual contracts, cyclical nature of the school year, etc.)? What can we do to overcome these challenges? What are the changes and forces external to schools that will change us (what will happen), and what are the changes internal to schools that are within our control (what do we want to have happen)? What does it mean to shift schools from being “teaching organizations” to becoming “learning organizations”? Which traditions are important to preserve, and which traditions hamper a shift to a long-term growth mindset? During these exercises, which yielded approximately 1,000 pieces of data from 250 school leaders, attendees organized their responses into four areas: school mission, people, the learning experience, and finance and operations. About 85 percent of the total responses came from heads of school, and the remainder from a combination of board presidents, trustees, and non-head administrators. I logged all of the Post-it note responses into a database and sorted them within each of the four categories. This sorting process is certainly subjective, and there is, of course, gray area and overlap among the responses (many notes could have been assigned to more than one of the four main areas) but the major areas of thinking were really quite unambiguous. What is sitting high in the minds of school leaders fell out of this process like the ripest of fruit falling from a tree. Here’s a roundup of school leaders’ most pressing issues by category. 1. School Mission There is real urgency in the need to push our vision and the horizons of our thinking. The basic school model is outdated and large portions of it must be redesigned at a foundational level. This urgency is relevant to schools that are thriving today as well as those that are struggling with finances and admission. We have to aggressively tackle changes to our culture and traditions. It is no longer reasonable to keep traditions because “that is how it has always been done” or because they have served us well in the past. While defining and sustaining truly core traditions, our school cultures have to become much more welcoming of change. We have to define our school’s real value in relation to changing markets and demographics. Some—perhaps many—independent schools are dangerously reliant on value that is now undifferentiated in a marketplace of expanding options for consumer families. 2. The Learning Experience We must shift to a model of learning that is more flexible, interdisciplinary, and focused on the interests, needs, and voices of the students. While not unanimous, there is broad convergence that student-driven, student-centric learning, which is fundamentally different from the teaching-centric model of the past, is relevant today and has a much better chance of being relevant in the future. Our culture of learning must unambiguously embrace risk, failure, and a growth mindset for both adults and students. Our methods of assessing student performance are broken. We must develop and use tools that assess what we actually value in student performance, which is not their ability to perform well on tests. The landscape of college admission and expectations for our graduates is likely changing, though in unpredictable ways. Colleges and universities are struggling with what they want to provide and who they want to admit in the future. It is unlikely that there will be a single solution to this problem in the near term, so we have to find a way to deal with that ambiguity. 3. People The shifting role of the teacher requires us to rethink how to hire, retain, and develop teachers who will have a very different set of roles with respect to their students, and how those students learn. We have to put more thought and resources into involving and educating parents about what is most important to our school and what they can expect for their investment in us. Parents need to understand the differentiated value proposition of the school they choose, and both what is and is not included in their investment. We should be developing board and leadership structures and skills that are better attuned to a changing dynamic and less predictable future. We have to rethink traditional boards comprised of noneducator parents and alumni selected largely because of their support and commitment to the school. Our parents and teachers are risk-averse for good reasons. We have to help our adults to become much more accepting of the value of risk-taking. We need to address rising costs within a paradigm of “always adding, never taking away” and already overworked teachers. We know where our largest costs lie, and we are either approaching or past a breaking point in continuing to expect more outcomes from the same set of people and the same set of job definitions. 4. Operations and Facilities There have been significant changes in the economic, business, and political landscape. In all three areas, the past is not sufficient as an accurate guide for the future, yet we must find a way to navigate a less predictable future—even though we don’t yet have the appropriate skills and resources to do just that. Most schools are operating with an outdated daily schedule and annual calendar structure. We know that the traditional use of precious in-school time is not optimal, yet few schools have really tackled this by making substantial changes in their daily and annual schedules. We need to rethink our physical spaces, specifically how to evolve them and be more efficient in their use. We have invested massively in buildings in the past, and we continue to compete in a facility “arms race,” yet we don’t align our use of these buildings with major changes we foresee in the learning experiences of the future. The Tipping Point In reflecting on these sessions with heads and schools and the issues that came to light from them, three themes emerge that help to describe the milieu of school culture today. First, there is a noticeable lack of reference to traditional benchmarks of “success” such as admission demand, financial strength, fundraising, and college matriculations. There is a growing recognition that those are artifacts, not drivers, of success. In a more stable—perhaps benign—recent past, those statistics were convenient measures of how well our schools were doing. School leaders now need to find a place for more nuanced measures of success such as cultural growth mindsets, innovation incubation, and evidence of “third horizon” thinking. While traditional data are useful, many of our schools’ most critical values, including noncognitive measures of student performance, are harder to measure, and those harder-to-measure areas may be more important to our long-term success in an increasingly strained marketplace. We are finally recognizing that schools, like nearly every other successful organization, need to develop, understand, and deliver a differentiated value proposition. And, in the case of our schools, traditional benchmarks can only tell part of that story. Second, as a group, school leaders understand that schools won’t change unless people change, and “people” includes boards, administrators, teachers, and parents. For generations, schools and our community of educators, parents, and alumni have largely prided ourselves on a level of congeniality which leaves the discernment and delivery of value largely up to individual interpretation. We only press hard questions and hard answers when the wolf is at the door, which is precisely the wrong time for big, probing, far-reaching discussions of our real collective vision and value. We can’t afford that anymore. Leaders recognize that we have to get the adults in our school systems singing from the same hymnal, aligned to a strong, differentiated mission, yet they also recognize that most of us don’t have the traditions, structures, or inherent skill sets to do that as well as we need. Finally, school leaders are beginning to see a real understanding that the silos around which schools have functioned for centuries simply must be broken down: engaging in change is the responsibility of “us.” Our teachers need to understand the real meaning of valuable innovation and how to lead those changes by becoming comfortable risk-takers. They need to evolve out of their traditional role as purveyor of knowledge and accept responsibility for helping to imagine and lead change from their key relationship with their students. Administrators need to learn the skills of effective change management that have never been part of educator training. Board members need to acquire greater understanding of a learning landscape that is increasingly different from the one in which they grew up, and we need to attract members to the board who truly understand this paradigm shift. We need to allow parents more opportunities for inclusion in expansive discussions about our learning model so they become, through increased exposure, more supportive and less fretful of change. For those of us who have observed the evolution of vision and strategy across independent schools for many years, and even decades, I would argue that we have crossed a tipping point. Leaders are increasingly recognizing that they must push their thinking to what we call the third horizon: ideas for future sustainability that may require fundamental reimagination and redesign of the traditional school operating system. Such rethinking can be uncomfortable. The single most powerful takeaway from the discussions with school leaders was this: We recognize that it is past time to push through the discomfort of change if we want our schools to thrive in the years and decades to come. There is no single simple answer to where and how our schools need to evolve, but it is powerful that school leaders collectively see the magnitude and the urgency of the issues that challenge us. In some, we will find consensus around the major component parts of potential solutions. And each leader can ensure that his or her respective community of school stakeholders is engaged in inclusive, provocative, horizon-pushing research and discussions that will both inform and guide value-generating change.