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.