Leadership & Legacy

October 30, 2025

Launching the 2025–2026 Leadership Development Program

Author

Kristin Bair O’Keeffe, Senior Writer & Editor

Kristin Bair O’Keeffe

Senior Writer & Editor

Kristin Bair O'Keeffe, a seasoned communications professional, joined Phillips Academy in 2012. In her early years, as the editor of Andover’s alumni magazine, Bair O'Keeffe not only shaped the publication’s content but also led a dedicated team of writers and graphic designers, orchestrating their talents to create a cohesive and engaging narrative.

Since 2018, Bair O'Keeffe has deftly balanced her time between two essential realms: the advancement team and the Tang Institute. For advancement, she skillfully crafts and conveys the Academy's philanthropic initiatives for the Outreach programs, the Addison Gallery of American Art, and the Robert S. Peabody Institute of Archaeology. At the Tang Institute, she contributes to the advancement of innovative education messaging, highlighting her passion for pioneering educational approaches. Bair O’Keeffe is also a novelist, speaker, and writing instructor with the Yale Writers Workshop.

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At the end of September, ten educators and school leaders from three schools gathered at Phillips Academy for the launch of the 2025 – 2026 Leadership Development Program (LDP). Now in its fifth year, this three-year retreat was dedicated to strengthening trust, cultivating reflection, and embedding values-based leadership into institutional life.

Held September 24 – 26, the program kickoff was an opportunity for participants to pause from the daily pace of school leadership and engage deeply with questions of community, ethics, and legacy. Drawing on the momentum of prior LDP gatherings, this year’s retreat built on the program’s commitment to preparing leaders who can navigate complexity with clarity and courage.

The objectives for this year’s program are threefold:

Build Community Around Shared Values — Strengthening trust through dialogue and reflection.
Reflect on Leadership Legacy and Impact — Exploring how daily choices shape culture and institutional memory.
Embed Reflection into Institutional Practice — Developing strategies to ensure ethical leadership becomes a sustained cultural norm.

Mary Kantor, Catholic Chaplain and Interfaith Advisor at Phillips Academy reflected that one of the most fruitful gifts of the kickoff was the opportunity to engage the “enthusiasm, eagerness, and interest” of fellow participants, each on their own professional trajectory yet with a shared aspiration to serve.

Leadership in Practice: Retreat Highlights

The retreat opened with a welcome reception and dinner featuring Rick Miller, president emeritus of Olin College of Engineering and founding chair of the LearningWell Coalition. Miller’s remarks set the tone for the days ahead, inviting participants to consider not only what they achieve in their roles, but also what legacy they leave behind.

Day Two centered on team building and ethical decision-making workshops. Through guided conversations, participants discussed tensions that leaders often face, including the challenges of balancing people and performance, tradition and innovation, principle and pragmatism. A lunchtime conversation with Dr. Raynard Kington, head of school at Phillips Academy, offered a thoughtful firsthand look at reflective leadership in action.

Day Two closed with an LDP alumni reception and dinner with Connie Yowell, executive director of the Center for the Future of Higher Education and Work at Northeastern University, who called on participants to think deeply about the nuances of leadership dilemmas. Yowell also engaged the group in a discussion about their individual aspirations for the program as well as their longer-term leadership goals.

On Day Three, participants turned their attention to embedding legacy leadership into a daily practice. The group engaged in a conversation on coaching and professional growth with Lisa Skeete Tatum, founder and CEO of Landit. By the program’s conclusion, attendees left not only with strengthened professional networks, but also with tangible strategies to bring back to their schools.

Leadership and Legacy

One of the elements that makes the LDP distinct is its focus on legacy-minded leadership. Rather than framing leadership solely as a set of skills or achievements, the program emphasizes the enduring impact of choices — large and small — on the communities served by participants.

The retreat’s framing drew inspiration from the Athenian Oath, where citizens pledged to leave their city “greater and more beautiful” than they inherited it. Participants were asked to consider a parallel question: What would it mean to leave our schools more just, more vibrant, and more trustworthy for the generations to come?

Fannie Deary, Director of Counseling at Pomfret School, shared that the invitation to consider one’s legacy was powerful, as was the message conveyed through the program that a leader’s legacy is never neutral. Matthew Sheehan, Phillips Academy’s Day Custodial Working Group Leader, expressed that the kickoff emphasized for him the importance of building a team-first culture in the name of meaningful, long-term impact.

Looking Ahead

The 2025 – 2026 LDP launches at a time when schools face heightened challenges — social, cultural, and institutional. By rooting leadership in reflection, ethics, and community, the program seeks to equip participants to manage complexity, while also modeling integrity and courage for their communities.

With this year’s cohort, the program continues to honor its central purpose: to prepare leaders who will have a meaningful and enduring impact on their schools and beyond.