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Stretching to Become a Flexible Leader

Lindsay LealArchived, Leadership Lab, Leadership Programs, Pedagogy Of Leadership®, Student Leadership

by Lindsay Leal, Dean of Students at The Taft School in Watertown, CT

In 2016, I had the incredible opportunity to attend the Gardner Carney Leadership Institute (gcLi) Leadership Lab. The week-long experience reshaped how I think about leadership, relationships, and my role as an educator. Today, as the Dean of Students at The Taft School, I am building on those foundational lessons through my studies in the University of Pennsylvania Graduate School of Education’s (Penn GSE) School Leadership program. Balancing the demands of my role at Taft with monthly travel to Philadelphia and the program’s rigorous coursework has been a challenge, but it has also been deeply rewarding.  

As I reflect on the journey from gcLi to Penn GSE, I am struck by how these experiences have shaped my approach to leadership and enriched my work at Taft. 

When I attended the Leadership Lab in 2016, I was seeking strategies to become a more effective leader in my school community. What I found was a program that challenged me to think not just about how I lead but why I lead. The gcLi’s emphasis on relational leadership was transformative. Through workshops, group discussions, and role-playing exercises, we explored how trust, empathy, and communication are the cornerstones of effective leadership. One session that particularly resonated with me focused on creating a culture of trust within organizations via the Consultancy Protocol. We examined how vulnerability and transparency can foster deeper connections, and I recognized that I am, most of the time, surrounded by a wealth of knowledge and solution-oriented colleagues. 

The gcLi also underscored the importance of adaptability. Every school community is unique, and effective leaders must tailor their approach to meet the specific needs of their environment. This lesson has stayed with me over the years, particularly as I navigate the complexities of my role at Taft. Most importantly, gcLi instilled in me a sense of leadership as service. I left the program with a renewed commitment to putting the needs of students, colleagues, and the broader school community at the center of my leadership practice.  

Fast forward to 2024, and I find myself in the midst of another transformative experience: the Penn GSE School Leadership program. This program is equipping me with the tools to address the challenges of modern educational leadership, from fostering equity and inclusivity to navigating the complexities of organizational change.  

As Dean of Students, my role involves everything from supporting student well-being to addressing disciplinary issues and fostering a positive school culture. Adding graduate-level coursework to that mix has been no small feat!

Each month, I travel to Philadelphia for in-person seminars, immersing myself in the program’s collaborative, cohort-based learning environment. These weekends are intense but invigorating. The discussions with my peers—fellow educators from diverse school contexts—are enriching and often provide fresh perspectives that I can bring back to Taft.  

The program’s emphasis on equity and justice has been particularly impactful. In one recent assignment, we analyzed how systemic inequities affect student outcomes and developed strategies for fostering inclusivity in schools. This work has pushed me to think critically about how I can make Taft a more equitable and inclusive environment, ensuring that every student feels seen, valued, and supported.  

Both gcLi and Penn GSE have enhanced my work at Taft in profound ways. The relational approach to leadership that I honed at gcLi has informed how I interact with students, faculty, and families. Meanwhile, the strategic and systemic tools I am gaining at Penn GSE are helping me to address broader institutional challenges with greater confidence and clarity.  

One of the key lessons from gcLi was the importance of listening—truly listening—to the needs and perspectives of others. This principle has been invaluable in my role at Taft, where I work closely with students navigating the complexities of adolescence. Building trust with students requires patience, empathy, and a willingness to meet them where they are (and avoiding the red zone!). The insights I gained at gcLi continue to guide me in creating a supportive and compassionate school environment.  

At Penn GSE, I am learning how to complement these interpersonal skills with data-driven strategies and evidence-based decision-making. This has given me both confidence as well as new tools to address challenges at Taft in a way that is both thoughtful and effective.  

One of the greatest gifts of these programs has been the opportunity to connect with other leaders who share a commitment to making a difference in education. At gcLi, I formed bonds with educators from across the country, and those connections have continued to inspire me and been a source of strength and guidance.  Similarly, the cohort model at Penn GSE has created a community of support and collaboration. My peers bring diverse perspectives and experiences, challenging me to think in new ways and broadening my understanding of what leadership can look like.  

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The time I spend traveling to Philadelphia each month provides a valuable opportunity for reflection. On the train rides back to Taft, I often find myself thinking about how I can apply what I’ve learned to my work as Dean of Students. These moments of reflection are a reminder of why I embarked on this journey in the first place: to become the best leader I can be for my school community.

As I continue to navigate the Penn GSE program, I am filled with gratitude—for the lessons I learned at gcLi, for the opportunity to grow at Penn, and for the privilege of serving the Taft community as Dean of Students. Leadership is a journey, not a destination, and I am committed to approaching it with humility, curiosity, and a deep sense of purpose.  

Both gcLi and Penn GSE have taught me that effective leadership is not about having all the answers but about asking the right questions. It is about creating spaces where every individual feels empowered to contribute and grow. This is the kind of leader I strive to be at Taft, and I am grateful for the tools and insights that these programs have given me to make that vision a reality. Looking ahead, my goal is to continue building a school culture that values equity, inclusivity, and connection. Whether it’s through supporting students in their personal growth, collaborating with colleagues, or implementing new initiatives, I am committed to leading with integrity and intention.  

In many ways, the journey from gcLi to Penn GSE is just the beginning. The lessons I have learned—and continue to learn—will shape not only my leadership practice but also the lives of the students and educators I have the privilege of working with. For that, I am profoundly grateful. 

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Lindsay is a graduate of Westminster School and Skidmore College, where she double-majored in economics and women’s studies and played lacrosse. She also worked as a summer counselor at Cape Cod Sea Camps in Brewster, Massachusetts. Upon graduation from college, she began her professional career in digital marketing. Over the course of eight years, she worked at various agencies and publishers in New York and Boston. In 2012, she joined the Taft faculty as a mathematics fellow. In her time at Taft she has served as a class dean, dorm head, Associate Dean of Students and now Dean of Students. Lindsay teaches math, coaches field hockey, leads winter yoga, and lives on campus with her dog, Scout. Lindsay is part of the 25th Cohort of the UPenn GSE School Leadership Program.