New View EDU Episode 89: Lessons from Retiring Heads

Available April 28, 2026

Find New View EDU on Apple Podcasts, Spotify, and many other podcast apps.

School leadership has always been a dynamic, evolving role, but never more so than in the past several years. As everything about education and the surrounding landscape changes rapidly, being a head of school requires more flexibility, tolerance for ambiguity, and innovation than ever before. On this episode of New View EDU, host Debra P. Wilson invites retiring heads of school Russell Shaw, of Georgetown Day School (DC), and Joan Buchanan Hill, of the Lamplighter School (TX), to share their learnings and lessons for future heads.

Joan and Russell reflect on the changes they’ve seen across their tenures, both within their school communities and in the external environment. As they discuss the importance of hands-on experiences and engagement with real-world challenges as crucial to the success of their schools, Debra brings up questions about how they view the advent of AI and its impact on education. Russell speaks about his view that one of the key strengths of independent schools lies in the ability to counteract the influence of technology through strengthening human interaction and genuine connection. Joan agrees, adding that while technology will always try to accelerate the pace of the world, the human experience and the developmental trajectory of students does not accelerate accordingly. Both advocate for strong leadership on the part of educators to help students learn important technology skills while balancing the scales in favor of off-screen learning.

That leads to a discussion about the idea of cognitive surrender, and how the ability of students to press a button and get hard things done for them has changed education. Joan and Russell speak about the challenge of helping students recognize that the struggle is the important part, and that real, sustained learning comes from not always having all the answers. They share their perspectives on how important it is for adults to model that stance, especially when it comes to technology, sharing their own uncertainties and acknowledging what they don’t know in order to partner with kids on navigating new online tools. Russell points out that the speed of technological evolution has meant students often understand more about it than the adults, which requires educators to seek partnership and leadership from students to help set direction.

Joan emphasizes that the leadership of young people, including younger faculty, is vital to the future of schools. She shares her perspective that younger faculty and staff often bring a different kind of resilience and joy to their work that may be missing for long-term educators, noting that the generational challenges younger people have faced has shaped their desire to make a positive impact on the world in a unique way. Russell agrees that there is much to be gained by approaching our work as lifelong learners, embodying our values and principles while navigating ambiguity. He articulates the need for leaders to be a “container for the community’s anxieties,” projecting calm and confidence while acknowledging that there may be multiple paths forward.

That calm demeanor, leaning into ambiguity, and being a keen observer within the community are key aspects to school leadership right now. All of these traits can help us gain clarity and live our values, Joan and Russell agree, which they say is critical to aligning leadership with the culture of a school community. They note the need to find a “fit” with the school and board in order to lead effectively; Joan cautions young leaders not to want the job so badly that they will become “imposters” in order to be hired, while Russell relates the experience of learning that effective leadership flows from loving the school and its mission enough to make the daily challenges worth the stressors. As they both approach retirement, their lessons of love, patience, engagement, and humility resonate for the next generation of school leaders.

Key Questions

Some of the key questions Debra, Russell, and Joan explore in this episode include:

• How has the landscape changed from the day you first walked into your schools to now? What’s different, and what’s constant?
• How do you think about balancing hands-on experiences for students with the pull of AI? What should schools be considering as they navigate new technologies?
• What does this moment call for in terms of leadership? If you were advising a new head of school now, what would you tell them to prioritize?
• How does philosophical or values alignment fit into school leadership? How important is “cultural fit” for successful headship?

Episode Highlights

• “I think that at our best, our schools can be counter-cultural and can sort of cut against the tide. And we have a world that is turning away from community, right? Our attention is being atomized. People are joining less things. Our schools do community really well. They give kids a model of what does it look like to collaborate, to engage with people who see the world a little bit differently than you do.” (9:53)
• “I’ve found young faculty members bring an esprit de corps, a “let's do this.” It's so fun to witness because sometimes the senior faculty are a little jaded. They're a little, you know, sick around the gills, if you will, but the young faculty know that they've overcome big things in their generation, maybe more so than in any other generation at such a compressed time. Global pandemic, that was a big thing. These deep economic difficulties and huge societal changes. And they persist. They continue to get up every day. They see the joy and the hope in their students, and they want to be part of it. They want to lead it.” (26:04)
• “I watch some of the young aspiring heads want it so badly. They'll say and do anything, but man, you’ve got to live that. And until you're able to really put one leg in the pant leg and the other and be willing to live it, and find that hill that you can all together rally around, then you become an imposter, you see? And when you're an imposter, you've got a short shelf life, because people don't want Memorex. They want the real thing.” (32:44)
• “But if you don't love the school with everything in you, if you don't feel deeply called to the mission of the school, the job is just too hard. You've got to believe in the place…These jobs, it's really hard. And you have to show up every day with this. I am doing important purposeful work. And I am going to persevere through the lawsuits and through the enrollment shifts and through the really knotty discipline issue, because I am, on behalf of this institution and mission, trying to serve some greater purpose.” (34:11)

Resource List

• Read two of Russell’s articles in The Atlantic, Let Your Kids Fail  and Lighthouse Parents Have More Confident Kids.
• Check out Joan’s conversation about resilience on the Learning From Leaders podcast with the Southwestern Medical Association.
• Learn more about Georgetown Day and the The Lamplighter School.

Full Transcript

• Read the full transcript here.

Related Episodes

• Episode 87: Making How Matter
• Episode 83: Mattering
• Episode 81: How AI Changes Everything and Nothing
• Episode 77: Dignity-Affirming Leadership in Schools
• Episode 67: Leadership Through Listening

About Our Guests

Joan Buchanan Hill is a recognized leader in experiential learning. She is a passionate advocate for excellence in early childhood education and independent school leadership. Joan is currently preparing to retire from her position as Catherine M. Rose Head of School for The Lamplighter School in Dallas.

Prior to her career in education, Joan worked in marketing and management, which propelled her to pursue a different field where she could more easily establish authentic connections and create positive change. After soul searching, she transitioned to a career in education.

Before joining Lamplighter, Joan served as lower school head at Columbus School for Girls (OH) and previously taught at Hawken School (OH) and University School (OH). Joan holds a bachelor’s degree in organizational communications from Ohio University, completed postgraduate studies in educational leadership from John Carroll University, and earned a doctorate of education in organization leadership from the University of Pennsylvania. Joan was an Each Moment Matters Luncheon Honoree in 2023 and is also currently active as a trustee on several nonprofit boards.

Russell Shaw has served as head of school at Georgetown Day School in Washington, DC since 2010. He has worked in the independent school world for more than 30 years as a teacher, dean, division head, assistant head, trustee, and more. He began his education career leading trips for Outward Bound in the Minnesota Boundary Waters. Russell is a frequent contributor to The Atlantic, where he writes on the intersection of parenting, technology, and education. He has presented on these topics in a range of settings including the Aspen Ideas Festival, Semafor, and the NAIS annual conference. He is co-leading the ARC Fellowship for Division Leaders through the Millenium Institute.