So, following a challenging assignment in a leadership role at a school that was transitioning from one leadership structure to another, I decided to take a one-year, self-funded sabbatical to explore independent school leadership: its organization, evolution, and maintenance.
During my research I visited more than 60 schools across the country. In a typical visit (see A Typical School Visit at the end of article), I meet with various members of the admin team, including the head of school, division directors, and advancement teams. We talk about the issues the school is grappling with, their leadership structure and how they feel it functions, and where they think the future of independent school education lies.
I’ve been to schools known for their innovative organizational structures, others for their cutting-edge academic programs, and others for their success (and struggles) with diversity and inclusion. I’ve been invited to look behind the curtain of some of the nation’s top schools, where I’ve had frank discussions with established heads and their teams.
As a result, I’ve learned a lot, not just about changing leadership structures, but about the challenges school leaders face—and their desire to discuss the state of our schools and share what they are doing. To that end, I share three overarching themes that consistently arose in my conversations with school leadership teams.
There are no mistakes, only lessons.
I have a dozen scripted questions that I typically ask during each visit, but my favorite one to ask school heads is: “If you could turn back time and redo one thing, what would it be and why?” These leaders have responded to this question with an astonishing level of openness, honesty, and vulnerability. The regrets they have expressed demonstrate that perceived mistakes are in fact indelible lessons.I have received a variety of responses to this question, but the majority were related to personnel matters. They wish they had a difficult conversation earlier. They wish they’d built relationships with faculty and staff at the beginning of their tenure. They wish they’d sought counsel from other school leaders instead of isolating themselves. Making tough decisions and handling them with compassion and grace is exceptionally difficult for heads; it requires experience and confidence that come with time, which is why these reflections were very often related to experiences early in their headships.
Many leaders also said they wished they had played a more active role in coaching their teams in order to internally develop stronger leaders. Given the myriad demands a head of school faces, it’s challenging to find the time to forge mentorships, but they are often the most rewarding endeavors for heads.
Some heads said that they wished they had dedicated more time and resources to creating an atmosphere of professional growth and learning. Many wished they had allocated professional development funds for the school leadership team, including the head of school and board chair, early in their tenures. We often think of professional development in terms of faculty and staff, but quite a few heads regret not taking the opportunity to earmark funds for their own growth and development, whether hiring a leadership coach or regularly taking a former head out to dinner.
School leaders also wished they were taking more risks. Heads often expect staff to challenge themselves, but they are not modeling this behavior personally. Emphasizing the idea of First Attempts In Learning (FAIL) is important and valuable. Faculty who see their leaders try something new and not succeed will feel much more inclined to step out of their own comfort zones. It is through trial and error that we grow and expand our learning.
In the course of many of these candid conversations, heads expressed a desire to expand their peer network. Leadership can be isolating, and sharing challenges and ideas with other heads can bring fresh perspectives and yield mutually beneficial relationships.
Leadership structures are shifting.
I entered the independent school world from public schools immediately following the Great Recession. I knew I eventually wanted to return to a leadership role, so I asked some of my school leaders for mentorship, and they generously devoted time and resources to developing me as a future independent school leader. In our regular meetings, I learned that prior to 2008, the head was very much seen as the instructional and daily leader of the school. Heads were tasked with being the “face” of the school, hiring the right people, and sustaining institutional memory.In the years immediately following the recession, however, heads had to tackle the challenges brought on by economic instability, which reshaped our school leadership structures. Hiring freezes, salary stagnation, and staff cuts brought the business aspect of independent schools to the forefront. This shift was felt universally and was discussed in all my visits. Whether considering the costs of adding distinctive programs, debating the sale of real estate holdings, or exploring the idea of tuition freezes, hard choices were a big part of those lean years.
As is so often the case, these challenges led to innovation and yielded new leadership structures that effectively serve our school communities today. Of course, there are lingering challenges like enrollment management, the annual fund, and tuition increases; however, schools have invented new tuition models, created additional revenue streams, and restructured themselves in a variety of ways.
As I began this project, I was particularly interested in the structure and organization of school leadership teams. I found that some schools have pretty traditional organizational charts, while others look like pieces of abstract art. Some schools don’t follow an organizational chart at all.
A few unconventional leadership structures stood out. A pre-K to grade-6 school has four different division heads (pre-K and kindergarten; grades 1/2; grades 3/4; and grades 5/6), all of whom are full-time teachers who hold their division headships for a designated term. A 9–12 grade school has both a president and head of school, both of whom report to the board; the president handles everything external (fundraising, community events, construction projects), while the head of school handles everything internal (enrollment, curriculum, faculty and staff). I visited a kindergarten to grade-8 school that has a three-person leadership team: head of school, head of internal affairs, and head of external affairs. The school doesn’t have division directors, advancement teams, or other groups.
While a number of K–12 schools continue to operate with a head of school and separate division heads, some schools that were seriously affected by the recession—in particular with enrollment declines—modified this model by combining division headships (lower/middle school head and an upper school head).
Other schools have moved away from division directors to a head of school who handles mostly external business, an associate head of school who handles finance and operations, and one or two assistant heads of schools (one for curriculum and one for enrollment management).
Another noteworthy trend, which is a direct response to the recession, is the addition of marketing and communications and diversity directors to senior leadership teams. These added voices bring issues like brand recognition and community-building front and center. Broadening the scope of the conversation in this way provides leaders with a much more holistic picture of a school and its operations.
Heads are wise to listen to and act on voices from within.
During my visits, I quickly realized that heads have a valuable resource that they’re often not aware of: teams and division directors who are eager to help shape and strengthen their schools but sometimes don’t know how to approach their heads with ideas or concerns. This desire to engage dovetails nicely with another common theme I heard about heads wishing they had stronger connections with their administrative teams.All of the people I met understood that their head of school has a lot of demands and many constituents, including the board chair, parents, the advancement team, academic leadership teams, and beyond. That said, a respectful dialogue emerged in which I heard what is working and what could be improved upon for our leadership teams. Suggestions for improvements ran the gamut from daily operations to strategic planning for the future.
One common desire across the board was having fewer meetings. More than half the schools I visited hold between six and eight leadership meetings a week (with various members at various meetings). Most people I spoke with believe this leaves too little time to be in classrooms to help teachers teach and learners learn. It also limits the presence of school leaders at recess, lunch, and drop-off and pick-up. Visible school leaders help strengthen a school’s sense of community—face time with students, teachers, and parents reinforces the bonds we are trying to form within our schools.
I visited a few schools that have reimagined the administrative retreat. Rather than planning longer retreats at the beginning or end of the school year, these schools have three or four daylong strategic planning retreats throughout the year. Spreading retreats over the course of the school year allows the team time to pause and reflect on the year’s progress while stepping away from the daily grind.
A number of heads I spoke with solicit performance feedback from faculty, staff, and the admin team through a midyear and end-of-year anonymous survey. They then discuss the issues that arise from the feedback at faculty meetings immediately following winter break and at the end of the school year. Since most of our schools ask middle and upper school students to fill out surveys on faculty members, it strikes me as good practice for heads to model what they want from the people who report to them. Heads who share this feedback publicly show that they are real people who, like everyone else in the school, are growing and learning.
During one school visit, I attended an admin team meeting led by the head of school. Each week the meeting begins with all team members ranking how they are feeling, both personally and professionally, from 1 (insecure) to 9 (confident). This exercise, while unconventional, offers a holistic view of each team member and a deeper connection among the school’s leaders. I was taken with how comfortable the team felt with each other, especially given that two of the members were new to the school. This practice fosters support and community among a group of people who often feel unable to let their guard down.
A final suggestion that came up in my conversations, which I found inspired, was for heads to set aside regular office hours each week where staff members can drop in without an appointment to discuss anything on their minds. This idea came from division directors who said time and time again that their faculty wanted access to the head at points throughout the year, rather than just at contract time. These office hours offer an opportunity for everyone on staff to feel heard by their boss, without having to make an appointment.
The personal is professional.
At first, this journey was about my personal growth, for me to determine if I wanted to remain an independent school leader and to explore how our schools are organized and what we’re doing to further independent school education. One thing is certain: This has been one of the most satisfying years of my career to date.When I started my nationwide outreach to heads, I didn’t anticipate the level of generosity and enthusiasm I would receive. After just a few visits, I realized that this endeavor was about more than my personal discovery.
It turns out that I was not alone in my desire for a big-picture view of independent schools; there’s a real hunger for information about how our schools function and meet the changing demands of education today. While I continue my research, I look forward to seeing what our leaders are doing to meet these challenges and how innovations inside our classrooms as well as our conference rooms are creating better independent schools nationwide.
A Typical School Visit
Tour the campus (30 minutes):Meet with the head of school to discuss
(30 minutes):
- Personal philosophy of being head of school
- Vision for the future of the school
- Advice he or she would give someone who is an experienced, yet still aspiring, school leader
Meet with other senior administrators to discuss (45–60 minutes):
- Specific role, duties, and how they came to be a part of that school’s admin team
- Vision for the future of their school department
- Functionality of the team structure (number of meetings, who attends, etc.)
- Advice they would give to someone who is an experienced, yet still aspiring, school leader
During school visits across the country, Nichols has also discussed such topics as:
- Employee recruitment and retention
- Salary scales, merit-based pay, motivation for raises
- Teacher observation and evaluation
- Professional development models
- Training for critical, difficult conversations
- Diversity, inclusion, equity, and community building
- Strategic planning