Middle Leaders: Keeping Perspective Amid the Daily Challenges

Most of what has been written about school leadership is aimed at heads of school or school principals. They seek guidance on issues far and wide, including governance, crises and legal issues, innovation and technology, and so much more. As a former school leader and lifelong learner, I tried to learn from the broad array of leadership advice from both inside and outside the world of education as I climbed the ranks in school leadership, taking on new roles and responsibilities every few years. Over the years, I’ve noticed that less leadership advice has been given to those who are, as I like to say, “caught in the middle”—division heads, assistant/associate heads, lead administrators, and assistant principals. They are the ones who navigate between and among the school head and other leaders at the school, including department heads, deans, and even the faculty.
 
Most of these “middle leaders” who gain responsibilities have little training or experience in managing the kinds of complexity that comes with such roles. These leadership roles are regularly asked to balance and manage the often-conflicting needs and priorities of multiple constituencies. With such work comes more experience, and many middle leaders use these roles as launching pads toward future headship.
 
Particularly in my two decades as an assistant head/division head, I often found it tempting to overthink or over analyze the best approach to my work, which can result in a sort of paralysis (and focus on the day-to-day responsibilities with less attention paid to long-term goals). During that time, I lived by five simple mantras.
 

Say “thank you.”

New York Times columnist David Brooks writes in an April 2022 article titled, “Globalization Is Over. The Global Culture Wars Have Begun,” that “human beings are powerfully driven by what are known as thymotic desires. These are the needs to be seen, respected, appreciated. If you give people the impression that they are unseen, disrespected, and unappreciated, they will become enraged, resentful, and even vengeful. They will perceive diminishment as injustice and respond with aggressive indignation.”
 
In my experience, middle leaders can so easily get caught in the daily challenges of school life that they miss—mostly unintentionally—the inspiring work that others are doing in the service of students, colleagues, and the school. In these roles, school leaders build a positive school culture by recognizing the important work done daily by members of the community. Expressing gratitude forms meaningful connective tissue.
 
During my years as a division head, I kept a list of faculty names in my top desk drawer and would put a checkmark next to each colleague for whom I had shared a handwritten note of thanks. People have a human need to be noticed for the little things. A handwritten note, a quick email acknowledgement of a tough moment managed, or a brief conversation in the hallway is simple and easy to do. It’s perhaps the most important thing any school leader can do.
 

See both sides, and “help me understand.”

Due to the roles’ close proximity to so many constituencies, major school problems tend to land on the desks of middle leadership first. The range of problems is infinitely wide: a cheating incident, a parent “concerned” about a teacher’s grading policy, a faculty member in conflict with a colleague about curriculum, a student treating a staff member poorly, another student being mean to a classmate, an overheard racist or sexist comment, a coach pressured to give an athlete more playing time. The list goes on.
 
As middle leaders hear the story that walks through the door, the temptation is to take it at face value. Yet the initial narrative often involves a more complicated story. I’ve learned that beginning conversations with “help me understand” allows a constituent to share their account, often revealing a multilayered, nuanced, and more complex take. This phrase also allows the other person involved to feel valued and heard regardless of final outcomes.
 

Keep an open mind, and admit “I could be wrong, but…”

Middle leaders are expected to have answers to complex issues or problems because they work closely with constituents at so many levels. Yet one of the most overlooked traits of strong leaders is one’s humility and ability to listen. Organizational psychologist Adam Grant talks about “confident humility”—knowing “how little you know and how much you’re capable of learning.”
 
Schools are filled with smart, caring, committed, and often-opinionated adults who want to hear what a school leader has to say about a particular issue or challenge. As a middle leader considers offering their point of view, a particularly effective way of introducing an idea is to lead with “I could be wrong, but… .” These simple words reflect humility, a willingness to entertain others’ thoughts, an opportunity to learn and keep a discussion going, at least until it is time to make a decision or move on. While this humble approach may lengthen a process, it will firm up salutary relationships, which in the long run are critical to healthy school culture.
 

Be honest, and share “I can’t promise…”

Nothing undermines trust in a leader more than overpromising and then under delivering. School leaders are often caught in situations where faculty make “demands” or try to push toward a decision in their favor. And a very human response can be to promise something (to get out of an awkward or uncomfortable moment if nothing else) that other circumstances or people might not allow.
 
Middle leaders often don’t have the authority to make final decisions, as the head of school or other colleagues often need to be included. While the result may seem obvious at the moment, it is important to hedge one’s bets in what are often complex and emotional situations.
 
Trust takes a long time to build and an even longer time to rebuild once lost; it can be easily lost if one promises what cannot be delivered.
 

Understand “it’s all part of the adventure.”

Working with young people and committed and strong-minded educators inevitably means that mistakes will happen. Students will behave badly. Parents will be too demanding. Teachers may not abide by clearly articulated policies. And when those things occur, emotions often get fiery and people get upset.
 
Middle leaders need to show empathy, patience, and compassion but also not take things too personally and keep things in perspective. Lightness and humor can quickly diffuse anger and frustration.

Middle leadership is an adventure, full of wonderfully gratifying and often unseen moments along with myriad frustrations. A grounding word or phrase, such as “it’s all part of the adventure” is critical to keeping perspective.

Those with significant school leadership responsibilities have complicated jobs engaging with a multitude of constituencies, multilayered issues, and complex human beings. Yet effective leadership often comes down to simple, sincere, and easily communicated words—and these have served me well during three decades of school leadership.
Author
Ben Snyder

Ben Snyder is former director of the EXCEL (Experiential and Community Engaged Learning) Center, former assistant head and head of upper school, and director of admission at Noble and Greenough School in Dedham, Massachusetts. He can be reached at [email protected].