How does one’s liberal arts college experience impact how they lead schools today? In this inspiring episode of Reach. Teach. Talk., Nat Damon gathers fellow Connecticut College Class of ’93 alumni—all current heads of independent schools—for a lively conversation on how liberal arts education, relational teaching, and shared values have shaped their leadership. Recorded live at the NAIS Conference in Nashville, this episode is a celebration of connection, purpose, and educational impact.

Suzanne Buck is the Head of School at Western Reserve Academy (OH), where she fosters strategic innovation, community building, and student-centered learning. A Connecticut College graduate, she earned degrees from Columbia (Social Work) and Harvard (Education). Suzanne has held leadership roles at Westminster, Fay, New Hampton, and Chatham Hall. She serves as Co-Chair of TABS and President of CCIS. Suzanne, her husband Johnny, and their family enjoy sports, puzzles, Maine summers, and their Labrador, River.

Sharon Howell is in her 5th year as the Headmaster of St. Johnsbury Academy, an independent school with a public mission in the Northeast Kingdom of Vermont. Earlier in her career she was the Head of School at Indian Springs School in Birmingham, Alabama, and the Associate Head of Northfield Mount Hermon School in Gill, MA. Before beginning secondary school leadership, she spent 15 years at Harvard University in various roles—PhD student in English and American Literature, curriculum developer for the Harvardx course Poetry in America, a Lecturer in History and Literature, and Dean of Adams House. She’s also a poet.

Derek Krein is the Head of Tilton School, a co-ed boarding and day school in New Hampshire. His career spans roles as a teacher, coach, advisor, and administrator, including positions in residential life, college counseling, and faculty leadership. A Connecticut College graduate, he credits Dr. Helen Regan for inspiring his path in education. Krein also serves as a Trustee at Indian Creek School and remains active with Kent School. He and his wife, Bobbi, have two college-age children.

Booth Kyle has been Head of School at Indian Creek School (MD) since 2019, bringing over 30 years of experience in education. He previously served as Associate Head at Lakeside School (WA) and worked in admission and financial aid at Deerfield Academy (MA). A Connecticut College graduate, he earned his M.Ed. from Boston University. Booth has served on the boards of Brooks School, The Enrollment Management Association, and the George Pocock Rowing Foundation. He and his wife, Colleen, enjoy gardening, dogs, and Boston sports.

Carson Smith has been Head of School at The Rumson Country Day School (NJ) since 2020, following 11 years as Middle School Director at Thayer Academy (MA). He previously served as Dean of Students at The Derryfield School (NH) and a teacher and department head at Cardigan Mountain School (NH). A Connecticut College graduate, he holds an M.A. from Columbia and an Ed.D. from Vanderbilt. Carson serves on the boards of Horizons at the Jersey Shore and Portsmouth’s School Board.

In this special episode of Critical Conversations brought to you by Reach Teach Talk, Nat Damon and Luthern Williams interview Richard V. Reeves, author of Of Boys and Men, in a conversation that explores the deep challenges facing boys and young men today. Using compelling data and heartfelt stories, Reeves discusses educational struggles, emotional health, masculinity, and the urgent need for societal change. Educators, parents, and mentors will be moved and inspired to rethink how we support boys in a world striving for gender equity—without leaving anyone behind. A must-listen for changemakers worldwide.

Richard V. Reeves is a best-selling author, public intellectual, and social commentator focused on inequality, class, and gender issues. He is the author of Dream Hoarders and Of Boys and Men, the latter praised by The New York Times and President Obama. A senior fellow at Brookings and President of the American Institute for Boys and Men, he has advised policymakers, led think tanks, and spoken at major global events. His TED Talk on modern masculinity earned wide acclaim. British-born, he lives in Tennessee with his wife and dogs and is the father of three sons.

In this powerful episode of Reach Teach Talk, renowned leadership coach Drew Kugler returns to Reach Teach Talk to share his transformative revelation: that leading through love—specifically strong and demanding love—is essential to great leadership. Reflecting on 26 years of coaching, Drew uncovers a red thread of love at the core of effective human connection. Educators, business leaders, and coaches alike will be inspired to lead more meaningfully, listen deeply, and elevate others by embracing love as a daily, intentional practice.

Drew Kugler (www.drewkugler.com) is a leadership and communication coach with over 30 years of experience guiding executives and teams across industries—from law and media to non-profits and consumer brands. Raised in San Diego by a city judge who believed deeply in integrity and respect, Drew learned early on the power of influence and the importance of listening. Over the past 30 years, he’s coached leaders across industries—law, media, nonprofits, and more—helping them navigate tough conversations and lead with what he calls Constructive Candor. He’s held leadership roles at Nordstrom and Marriott, taught communication at San Diego State, and spoken at institutions like Stanford, NYU, and UCLA. Drew is especially proud to work with all communities nationwide and to serve as faculty at Hebrew Union College and the Board of Directors at Reach Academy for Young Men.

In this episode of Reach, Teach, Talk, Dr. Michael Gurian, a leading expert in gender studies and neurobiology, explores why boys need a "rescue plan" in today's world. He breaks down how brain science, school structures, and social isolation impact boys' learning, behavior, and emotional health. Discussing depression, aggression, and technology’s role in disconnecting boys, Dr. Gurian shares practical strategies for parents and educators to better support them. This powerful conversation challenges common misconceptions and highlights how relationships and school culture can help boys thrive. Tune in for game-changing insights into raising and educating boys today!

Dr. Michael Gurian is a marriage and family counselor, New York Times bestselling author of 32 books, and a leading expert on gender and brain science. He co-founded The Gurian Institute, which conducts global research and professional training. Michael has spoken at the United Nations, advised the White House, and briefed Congress on the boy crisis in America. His books, including The Wonder of Boys and Boys and Girls Learn Differently!, have sparked national debate. A dynamic speaker, he uses case studies and brain scans to help educators, parents, and organizations better support learning, development, and human connection.

Students ask these questions all the time—but how often do we truly consider the role of purpose in education?

In this episode, I sit down with Ross Wehner, founder of World Leadership School, a visionary in experiential learning, a former journalist, and an inspiring thought leader. Together, we explore how purpose fuels motivation, engagement, and collaboration—and why cultivating a purpose-driven school culture is essential for students' mental, emotional, and academic well-being.

Because in schools that prioritize purpose, no one walks alone—and in today’s world, that truth has never been more important.

Join us for this powerful conversation!

Ross Wehner is a writer, social entrepreneur, and Founder of World Leadership School, which “partners with K12 schools to reimagine learning and create next-generation leaders.” Ross also co-founded the nonprofit TeachUNITED, which works to transform learning at rural schools around the world. Ross is guided by the question: How can K12 school become the ultimate platform for launching students into lives of purpose?

Ross is an author who is working on a book that explores Purpose Learning at schools around the globe. He facilitates the Salmon River Program for School Heads, a leadership development program that begins with a rafting adventure on the Salmon River in Idaho. Ross is a frequent keynote speaker on the future of K12 learning. His Tedx talk “What if the Purpose of School Were Purpose?” was recently selected for the TED platform and has received over 275k views.

Ross began his career as a journalist in Chile and Peru in the 1990s. He received a Master’s in Latin American literature and worked as a wilderness educator for the National Outdoor Leadership School and as a classroom teacher at two independent schools. He lives in Boulder, Colorado, with his wife and two children.

What happens when creativity is seamlessly woven into every aspect of a classroom and school day? The possibilities are endless. In this episode, Nat sits down with Peter Nilsson—educator, thought-leader, musician, and advocate for AI as a creative partner. Peter is also the mastermind behind A Boarding School Musical and is currently developing his second production, Schooled. Join us for a fast-paced, inspiring hour as we explore how creativity lies at the heart of great teaching. Prepare to be inspired and “tricked” into learning through Peter’s unique take on relational creativity.

Mr. Peter Nilsson is the founder of Athena Lab and the editor of the weekly education newsletter The Educator’s Notebook. He has served as head of school, administrator, teacher, tutor, and coach in schools for over 20 years. Most recently, he returned in the summer of 2023 from overseas as Head of School at King’s Academy, a coeducational boarding school in the Middle East founded by King Abdullah II of Jordan. Before that, he taught, coached, and served in a variety of administrative capacities at Deerfield Academy in Massachusetts.

Also a musician, Peter practiced in New York City for four years, where he composed and performed with a jazz trio, funk band, hip-hop performers, classical ensembles, off broadway theater, and musical theater. At Deerfield, he produced A Boarding School Musical, in which 25 faculty and staff members surprised the student body with a one act, Hamilton-style performance at a school meeting. This production is the source inspiration for Schooled: the Musical, presently in development.

Peter serves on the advisory boards for SXSWedu and the Center for Curriculum Redesign, both of which drive innovation in education across the United States and around the world. He also serves on the advisory team for the Middle States Association Responsible AI in Learning endorsement. He is a trustee at the Canterbury School. To learn more about Peter’s work, you can subscribe to the Educator’s Notebook, in which he circulates education and learning related news from around the web for the purpose of promoting innovation in education, or visit www.peternilsson.us.

He lives in Fort Wayne with his wife Crystal and their two children.

Shaila Kapoor has spent two decades launching tech products and leading marketing in software, cellular, and biotech. Her true passion, however, lies in education. She has co-founded a charter school in underserved California, created education software during COVID, and advanced girls’ education in northern Pakistan and Afghanistan.

This year, she launched Boys Who Write, a global nonprofit fostering boys' communication skills to enhance emotional well-being, build meaningful relationships, and thrive as community leaders. The program combines male mentorship, a love for reading and writing, and relationship-building skills in a virtual format, connecting boys across diverse boundaries.

Unlike traditional online learning, Boys Who Write uses a dynamic broadcast style inspired by gaming streams and travel shows, paired with custom games and tools. This immersive approach nurtures academic, social, and emotional growth, addressing the critical communication challenges boys face today.

Rites of passage honor the transition from boyhood to manhood. But what is a rite of passage? How are they effective at raising self-aware young men? Learn from engaging and deeply thoughtful educator, Dr. Mark Dowley, whose life work is centered around these themes—in schools and in greater society.

Dr. Mark Dowley is the co-author of the Classroom Management Handbook and Director of Programs at the Foundation for Positive Masculinity. For over 15 years, Mark has taught and presented in schools from Papua New Guinea to New York and has received multiple teaching awards. He facilitates rites of passage programs as part of his role at Brighton Grammar School in Melbourne, Australia with the goal of increasing the engagement and learning of boys and young men.