Cultivating Leaders: Five Reasons Why Schools Struggle

I consider myself lucky to have worked at several reputable schools over the course of my decade-long career in independent schools. The organizations I worked for enthusiastically supported my professional development through various workshops, conferences, and coursework. I’m the educator and leader that I am today because independent schools believed and invested in me. I also consider myself fortunate to have come across countless supportive colleagues, families, and bosses. If you’re a veteran of independent schools, similarly, you know that it’s the relationships that make these communities special.
But even robust professional development budgets and supportive people couldn’t provide what I needed to take the next step in my leadership development—what I didn’t even know I needed. A mentor. As a school leader, I know how much thought schools put into mentorship programs for new faculty, and having experienced these programs myself when I was new to a school, I’ve appreciated knowing that there was someone that I could go to for questions and concerns. However, “guide” rather than mentor is a more applicable term for an existing faculty member who supports incoming personnel. The shift in terminology isn’t meant to take away from the importance of guides, but it does differentiate between the typical support of new faculty and the unique role that mentors serve.
Faculty guides are critical to the smooth onboarding of new personnel every year, but there is plenty of room to think more intentionally about supporting growth, particularly for administrators in their first leadership roles or in new leadership roles. 

An Uncommon Relationship

Reflecting on my first leadership role as a lower school associate head at a PK–12 independent school, I realize it was a humbling and rare experience. I am so thankful for the patience and forgiveness of the faculty members I supervised. I stumbled repeatedly, and at times, I just didn’t know how to get out of my own way. I am also deeply indebted to the only person in my career who I identify as a mentor—a senior leader in the school community, but not my direct supervisor or someone who was assigned to me.
By virtue of our roles and overlapping professional interests, a strong work relationship with this person was cemented immediately. We talked shop for hours on end and tackled thorny problems together. My knowledge of the independent school landscape grew exponentially as I learned to appreciate the complexities of my role. Concurrently, the mentoring aspect of our relationship developed through trust and affinity, growing in ways that often had little to do with work: invitations to weekend gatherings with family and friends; scoping out the best restaurants when we traveled to hiring fairs; and inquiring about the birth of my nephew or the health of an ailing family member. My mentor became my sounding board, confidante, and friend.

Mentorship is about vulnerability and honest conversations—two humans creating a space together dedicated to growth. Mentorship typically forms organically, resulting from self-selection rather than assignment. A relationship like this is hard to come by. Given the rarity of such relationships then, what can schools do to be more intentional about leadership development?

Supporting New Leaders

Most schools aren’t structured to support leadership development beyond the growth that occurs as a byproduct of tenure or sending people to the occasional conference. It’s often assumed that a supervisor, such as a division head or another senior leader, will facilitate the development of new or junior leaders, but in practice, there are five reasons this promise typically goes unfulfilled:
Training. Most supervisors are not trained to develop the adults around them. Most independent school leaders get their start in education working with children, and when they begin to work with adults, they need years to get comfortable with the developmental differences.
Bandwidth. Senior leaders don’t always have the capacity to help develop the leaders in their charge. The phrase “my door is always open” is meant as a sincere invitation, but in my experience, bosses are often short on time to support leaders in an intentional way.  
Evaluation. There is inherent conflict between vulnerability and evaluation. Leadership positions in independent schools are competitive roles, and new leaders often feel compelled to “put their best foot forward” to uphold a competent image. And yet, openly reflecting on mistakes serves as some of the best fodder for professional growth. But if the same information that can help you grow is also the information that can be held against you in a performance evaluation, many people may feel that there’s a strong disincentive in opening up to their boss. 
Process. With an endless supply of “fires to put out,” administrators understandably adopt a problem-solving stance geared toward efficiency and expediency, an approach that can inadvertently undermine the nonlinear process of professional growth in others. Inquisitive, nonjudgmental spaces are required to suss out the personal assumptions, past experiences, and gremlins that people unwittingly integrate into their leadership style.
Proximity. The adage “it’s lonely at the top” can apply to school leadership, and in rare instances when a supervisor is the issue, new leaders may not feel that they can go to anyone else in the organization for fear of being seen as unprofessional, a gossip, or undermining their bosses.  

Next-Level Support

While mentorship can be an important asset for new leaders, these connections are uncommon and take time to grow. For those who have difficulty finding a mentor, leadership coaching can provide the boost that sustains new leaders through the challenges of a professional transition. Coaching, like mentoring, can lead to more effective leadership up front and carries implications for recruitment, retention, and organizational development.

Coaches are trained to work specifically with adults, providing a dedicated time and confidential space for leaders to reflect on their progress. Removed from the context of the workplace, coaching conversations enable leaders to honestly discuss their vulnerabilities and growth edges, which can be especially useful for thinking out loud about workplace conflict. The conversation allows for the kind of wandering and wondering that helps leaders connect the dots between current behavior and ideal performance.
As with any potential solution, there are a number of factors to consider when determining whether coaching is an appropriate support for new leaders at your school. Coaching can be resource-intensive, and schools are constantly making decisions within the realities of their financial constraints. Coaching engagements that last several months are comparable in cost to national conferences, so schools weighing these two options would need to give thought to the value of transformative day-to-day coaching relative to the networking and new knowledge that conferences offer. Additionally, choice is a crucial component of a successful coaching relationship––leaders need to both opt in to coaching and have a say in who they work with. Given the vulnerable nature of coaching relationships, assigning someone a coach without their input can lead to a strained process and tepid results.
As anyone who’s made the jump from teaching to leading knows, the challenges embedded in working primarily with adults are numerous. To use the terminology of leadership scholar Ron Heifetz, the greatest challenges that independent school leaders in transition face aren’t technical (i.e. those that can be solved with expert knowledge) but rather adaptive (i.e. complex and ambiguous, requiring internal transformation). To support new leaders more fully, schools must commit not just to intention but to action.
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Zakaria Sherbiny

Zakaria Sherbiny is the founder of First Rodeo Coaching, an organization dedicated to supporting independent school leaders in new roles, as well as leaders seeking to privately develop their diversity, equity, and inclusion competencies.