2026 Heads of School Retreat and Annual Association Meeting
AISNE 2026 Heads of School Retreat | January 27 – 29, 2026
Join us for our 2026 Heads of School Retreat and Annual Association Meeting. We are excited to come together for a few days of community, laughter, learning, and growth. Engage in thought-provoking discussions, hear from world-class speakers, share experiences, and connect with fellow school leaders. Whether you are new to the AISNE community, or a familiar face, you will find this in-person gathering stimulating and reinvigorating.
Pricing and Hotel:
$769/pp. This event is exclusively for AISNE Members. Registration does not include hotel accommodations.
REGISTER HERE
Hotel Information
Wentworth by the Sea
588 Wentworth Rd
New Castle, NH 03854
Group rate: $179.00/nt + taxes, based on availability. This room rate expires on January 5, 2026.
Limited discounted rooms remaining! Make your reservation today.
Agenda at a Glance
Tuesday, January 27
- 5:00 – 6:00 PM | Welcome Reception, sponsored by Rockland Trust
- 6:00 – 8:30 PM | Dine on Your Own, or Small-Group Dinners
- 8:30 PM – | Cocktails & Conversations
Wednesday, January 28
- 8:00 – 9:00 AM | Breakfast
- 9:15 – 10:45 AM | Top Traits of Transformational Leaders with Bradley James Davies (Heads in Years 1 – 3)
- 9:15 – 10:45 AM | Deepening Impact & Sustaining Leadership with Allison Gaines Pell and Todd Bland (Heads in Years 4+)
- 11:00 AM – 12:00 PM | Topic Sessions 1
- 12:00 – 1:00 PM | Lunch
- 1:15 – 2:45 PM | General Session with Steve Brown
- 3:00 – 4:00 PM | Topic Sessions 2
- 5:15 – 6:00 PM | AISNE Annual Meeting
- 6:00 – 7:00 PM | Cocktail Hour, sponsored by Olson Lewis + Architects
- 7:00 – 8:30 PM | Dinner, sponsored by TIAA & Fiducient Advisors
- 8:30 PM – | Cocktails & Conversations
Thursday, January 29
- 6:00 – 7:00 AM | Morning Activities
- 7:45 – 8:45 AM | Breakfast
- 9:00 – 10:00 AM | General Session with Dr. Bertice Berry
- 10:15 – 11:15 AM | Topic Sessions 3
- 11:30 AM – 1:00 PM | Closing Session with Steve Brown
- 1:00 – 1:30 PM | Lunch & Farewell
General Sessions
Wednesday, January 28 | 1:15 – 2:45 PM
Steve Brown | Leading from the Future: An Introduction to Strategic Foresight for Heads of Schools
In today’s volatile, uncertain, complex, and ambiguous (VUCA) world, traditional strategic planning often falls short. The challenge for school leaders is to move beyond static, long-term plans and cultivate a more adaptive approach to strategy—one that sets a clear direction while building the capacity for continuous learning and adjustment. Over two sessions, we will explore the dynamics shaping the futures our students will inherit, imagine preferred futures for our schools, and map the steps needed to make that future a reality. The goal of these sessions is to introduce you to a set of tools and frameworks you can use to equip your schools not with a fixed map, but with a reliable compass and a guiding ‘north star’ to navigate the complexities of leading your institution into the future.
Steve Brown began his career as a high school teacher and coach, spending seventeen years in the classroom before becoming intrigued by the challenge of organizational change—particularly why schools adapted so slowly to change in the world. This curiosity led him to pursue graduate studies in the dynamics of change within organizations and communities. Steve helped establish Southern New Hampshire University’s (SNHU) College for America, an innovative competency-based program for working adults, and later served in SNHU’s Strategy and Innovation Center, where he supported executive foresight and strategy, coached leaders and cross-functional teams navigating change, and partnered on programs for leading in complexity. He founded The Futures Collaborative to help organizations and individuals understand, embrace, and navigate the uncertainties of our rapidly changing world.
Thursday, January 29 | 9:00 – 10:00 AM
Dr. Bertice Berry | The Story You Tell: Purpose, Belonging, and the Heart of Transformational Leadership
Dr. Bertice Berry invites you to reconnect with your sense of purpose and to use storytelling as a tool for transformation—both personally and institutionally. Drawing on her powerful work in leadership development, belonging, and internal wellness, Dr. Berry explores how we can build stronger cultures by learning to tell our stories to one another first, and then to the world. Storytelling bridges the past with the future and can illuminate the values, mission, and shared humanity that sustain thriving school communities.
Sociologist, Bertice Berry, Ph.D. is a best-selling author award-winning lecturer and has been named Comedian of The Year, Lecturer of the Year and Entertainer of the Year. She has published 14 best-selling books in both fiction and non-fiction and has won numerous awards and accolades for both her writing and presentations. Berry has had her own nationally syndicated television show and has hosted, interviewed and made numerous television, documentary and radio appearances on a variety of diverse venues including The Tonight Show, Oprah Winfrey, Between The Lions, Crossfire, 20-20, NPR, PBS, Comedy Central and CNN.
Detailed Agenda
Tuesday, January 27
5:00 – 6:00 PM | Welcome Reception, sponsored by Rockland Trust
Join us for our welcome reception filled with connection and conversation as we kick off the 2026 Heads of School retreat. Enjoy light refreshments, drinks, and the opportunity to network with fellow leaders in an inviting atmosphere.
6:00 – 8:30 PM | Dine on Your Own, or Small-Group Dinners
Take the evening to unwind and enjoy dinner your way. You may choose to explore local restaurants with colleagues for a group dining experience or venture out on your own to sample the Portsmouth area culinary options. Sign-ups will be made available to interested parties via Sign-Up Genius.
8:30 PM – | Cocktails & Conversations
Cap off the evening with good company and great conversation at Salt Kitchen & Bar located inside the hotel. Enjoy a relaxed atmosphere and the chance to chat and unwind with fellow attendees.
Wednesday, January 28
8:00 – 9:00 AM | Breakfast
9:15 – 10:45 AM | Heads of School Sessions
Year 1–3 Heads: Next-Level Listening—How to Listen Like Your School Depends on It. Because It Does.
Presented by: Bradley James Davies, Author and Facilitator
Independent schools are complex, diverse communities where leaders must navigate a wide range of perspectives, beliefs, and needs. Success hinges on one skill above all: the ability to listen—truly listen—because your school depends on it. In this interactive session, we will explore the science of listening, learn the do’s and don’ts of effective communication, and practice crafting powerful, transformative questions. Using real-world scenarios—from engaging with upset parents to addressing faculty concerns and supporting students in crisis—you will gain practical tools to strengthen relationships, lead with empathy, and make a bigger impact both at school and at home.
Year 4+ Heads: Deepening Impact & Sustaining Leadership
Presented by: Allison Gaines Pell, Senior Consultant and Todd Bland, Leadership Support Consultant | Carney, Sandoe & Associates
For heads of school who have moved beyond the early years of leadership, the challenges shift from learning the fundamentals to sustaining impact, deepening influence, and leading with resilience. This session invites you to bring forward a current leadership dilemma and engage in a structured, dilemma-based protocol designed to tap into the collective wisdom of the group. You will have the opportunity to receive and provide peer feedback in both small- and large-group settings, creating a brave space to explore real challenges, consider multiple perspectives, and reflect on new possibilities. Supported by facilitators, we will engage together in thoughtful analysis, collaborative problem-solving, and generative dialogue with colleagues who understand the complexities of leading independent schools. By the end of the session, you will leave with actionable strategies, renewed clarity, and strengthened capacity to sustain your leadership impact, support your school community, and continue growing as visionary and resilient leader.
11:00 AM – 12:00 PM | Topic Sessions 1: Strategic Leadership and Adaptive Thinking
Finding Opportunities in the Chaos: Strategic Thinking Approaches for Independent Schools
Presented by: Brad Bates, Head of School | Dublin School (Dublin, NH)
Many Heads of School lament that their strategic plans are outdated as soon as they are completed. This session introduces strategic thinking as an alternative to traditional planning, using John Doerr’s Measure What Matters as a framework. Together we will explore how objectives and key results (OKRs) can help prioritize initiatives, motivate stakeholders, pivot naturally, and celebrate success. The session will also share how one small school applied OKRs in a comprehensive campaign. You will learn how to create strategic categories for school improvement and fill them with objectives and key results rooted in your mission and values. We will explore how to delegate ownership, measure progress, evaluate relevance, allocate resources, and incorporate strategic thinking into campaigns.
Clarity, Courage, & Connection: Developing a Justice-Centered Reflective Practice of Leadership
Presented by: Charlotte Jacobs, Director, Independent School Teaching Residency | University of Pennsylvania Graduate School of Education
Periods of transition—whether driven by shifting school cultures, leadership changes, evolving community expectations, or external pressures—can leave school leaders feeling unanchored. Drawing on her groundbreaking work on Justice-Centered Reflective Practice (JCRP) in Schools, University of Pennsylvania Adjunct Associate Professor Charlotte Jacobs will guide you in exploring what it means to lead with intention and humanity during times of uncertainty. Through a blend of research, real-world case studies, and interactive discussion, we will examine the potential of the JCRP tenets to serve as framing approaches for your own leadership practice, as well as for the professional development of your school faculty and staff. This session will offer practical frameworks and tools for communicating amid ambiguity, supporting faculty and staff during change, and making values-aligned decisions when the path ahead is still taking shape. You will leave with strategies to strengthen your leadership presence, cultivate resilience across your communities, and harness JCRP as fertile ground for possibility and growth.
12:00 – 1:00 PM | Lunch
1:15 – 2:45 PM | General Session with Steve Brown | Exploring the Future: From Anticipation to Imagination
This session will introduce school leaders to the discipline of strategic foresight. We will explore the VUCA world and learn how to use foresight to anticipate and prepare for change. We will work with a set of plausible future characteristics for the year 2037 to create scenarios, identify critical planning issues and uncertainties, and begin to imagine a preferred future for your school. We will conclude by reflecting on how this imaginative work is the essential first step in building a truly adaptive strategy.
3:00 – 4:00 PM | Topic Sessions 2: Talent, Governance, and Leadership Sustainability
Strategic Planning for Independent Schools: Staying Mission-Driven Amid Change and Challenge
Presented by: Susan Angelides, Head of School | Cambridge Montessori School (Cambridge, MA)
In today’s rapidly changing landscape, independent schools face the paradox of being both timelessly mission-driven and endlessly adaptive to new demands. This session explores how you can engage boards, faculty, staff, and parents in a strategic planning process that builds trust, sets priorities, and strengthens long-term sustainability. The session also emphasizes the importance of clear and specific language in final plans so that goals are measurable, responsibilities are explicit, and progress is transparent. You will leave this session knowing how to move beyond a static five-year plan toward a living, adaptive framework that guides decisions.
Attracting and Retaining Talent in a Multigenerational Workforce
Presented by: Lise Charlier, Head of School | The Cambridge School of Weston (Weston, MA) and Kim Ridley, Head of School | Fayerweather Street School (Cambridge, MA)
Heads of School Lise Charlier and Kim Ridley will share their experiences and strategies for navigating today’s multigenerational workforce. In this session you will learn how to decode generational dynamics, attract and onboard mission-aligned faculty, cultivate engagement through empowering leadership, adapt to the needs of a diverse team, and strengthen retention with clear pathways for growth, belonging, and professional satisfaction.
From the Sprint to the Marathon: Lessons Learned (Professional and Personal) from Long-Term Service
Presented by: Allison Gaines Pell, Former Head of School at The Wheeler School (Providence, RI) and Todd Bland, Former Head of School at Milton Academy (Milton, MA)
In an era where the average tenure of heads of school continues to shorten, this session draws on the experience of long-serving leaders to offer context, insight, and practical strategies for sustaining one’s work with intention, purpose, and resilience. Allison and Todd will share candid reflections on what contributed to their longevity—including lessons learned from successes, challenges, and missteps—and discuss how strong support systems and the cultivation of leadership capacity in others can help sustain both the individual and the institution. Together we will also review current trends in headship tenure and engage in guided reflection to clarify the supports you need to thrive throughout your own leadership journey.
Dynamic Duos: Building a Strong Board Chair/Head of School Partnership to Strengthen School Leadership
Presented by: Gabe Burnstein, Head of School and Kate Paglia, Board Chair | Charles River School (Dover, MA)
At the heart of every high-functioning independent school is a collaborative and aligned relationship between the Head of School and the Board Chair. This session reframes that partnership as a co-leadership model—emphasizing interdependence, shared vision, and intentional communication. Drawing on their three-year experience at Charles River School together, Gabe Burnstein and Kate Paglia explore strategies for building trust, clarifying roles, aligning strategically, and navigating transitions, while offering practical tools for effective communication, shared leadership, and reflecting on how identity and school dynamics shape leadership experiences.
4:00 – 5:00 PM | Break
5:00 – 6:00 PM | Annual Meeting
6:00 – 7:00 PM | Cocktails, Connection, and Collaboration, sponsored by Olson Lewis + Architects
After a full day of sessions and the annual meeting, unwind at our Day 2 cocktail reception. Enjoy a curated selection of drinks and light bites while mingling with fellow attendees in a relaxed, welcoming atmosphere.
7:00 – 8:30 PM | All-Attendee Dinner sponsored by TIAA and Fiducient Advisors
8:30 PM – | Cocktails & Conversations
Cap off our first full day together with good company and great conversation at Salt Kitchen & Bar located inside the hotel.
Thursday, January 29
6:00 – 7:00 AM | Early Morning Activities
- Fitness Center
- Pool
- Walk & Talk
7:45 – 8:45 AM | Breakfast
- All-Attendee Breakfast
- MAIS Meeting Breakfast
- VISA Meeting Breakfast
9:00 – 10:00 AM | General Session with Dr. Bertice Berry (see above)
10:15 – 11:15 AM | Topics Sessions 3: Wellbeing, Community, and Student Centered-Leadership
Crisis Communications: Strategies for School Communications in a Crisis Situation
Presented by: Brian Bloomfield, Head of School | Lyndon Institute (Lyndon Center, VT)
In a crisis, schools are often told to consult lawyers, follow policy, and say as little as possible. Yet remaining silent can create its own challenges, allowing rumors and mistrust to fill the void. This session explores how school leaders can navigate the delicate balance between caution and transparency. We will examine how to identify the story that needs to be told, communicate with integrity, and minimize harm—acknowledging that both speaking and staying silent carry risks. Practical strategies for thoughtful, values-driven messaging will be discussed to help you lead effectively in moments of uncertainty.
Leading Well: Replenishing Energy, Building Community and Sustaining Impact
Presented by: Dr. Jennifer Bryan, Psychologist | Re-Set School
Modern leadership can be exhilarating, but it also brings significant personal and emotional demands—particularly for women heads of school. This panel draws on insights from a cohort experience led by educational consultant Jennifer Bryan, and highlights how an ongoing facilitated group provides a supportive space to explore strategies for recovering from emotional depletion, reducing professional isolation, and building sustainable leadership practices. Join the panel in exploring this accessible, affordable and meaningful way of sustaining wellbeing.
Panelists (from L to R):
Danielle Heard, Head of School | Nashoba Brooks School (Concord, MA)
Sophie Lau, Head of School | Lincoln School (Providence, RI)
Sara Pelmas, Head of School | Beaver Country Day School (Newton, MA)
Top Traits of Transformational Leaders: How to Crush It Without Getting Crushed
Presented by: Bradley James Davies, Author and Facilitator
School leadership is both deeply rewarding and relentlessly demanding. Too often, the pursuit of excellence leaves leaders exhausted, overextended, and disconnected from the purpose that first drew them to this work. Drawing on decades of experience leading schools and coaching leaders, Davies explores the traits and habits that define transformational leaders who create lasting impact without sacrificing their own wellbeing. This lighthearted yet honest session blends practical insight with personal reflection. Davies challenges you to rethink what it means to lead effectively, offering two core truths: the best way to become a better leader is to become a better person, and the only way to elevate one’s leadership impact is to do less and be(come) more. Together we will engage in a guided self-assessment and create a personalized wellness plan designed to support both professional success and personal sustainability. Through humor, vulnerability, and real-world examples, this session offers a roadmap for “crushing it” as a leader without getting crushed in the process.
Leading Through the Storm: A Head of School’s Guide to Helping Students Navigate Mental Health Challenges
Presented by: Nichol Ernst, CEO & Clinical Director | Summit Achievement
Mental health challenges among students—such as anxiety, depression, and substance use—can deeply affect the life of a school community. In this interactive session, Nichol Ernst will provide practical guidance on how to support students while maintaining community integrity. Drawing on decades of experience in independent schools, Nichol will help you rethink your approach to student mental health, leverage existing campus resources, and collaborate effectively with third-party support systems. Together we will explore strategies for supporting student retention and reintegration after medical leave, engage in small-group exercises, and leave with practical tools to strengthen a healthy, sustainable school-wide mental health culture.
11:30 AM – 1:00 PM | Closing General Session with Steve Brown | Building the Future: From Vision to Action
Building on the foresight and preferred futures developed in Exploring the Future, this session will focus on mapping the path from the present to the desired future. Using the Three Horizons framework, we will have a structured conversation to identify the aspects of the current model that are losing relevance (Horizon 1) and the “pockets of the future” that contain elements of the desired state (Horizon 3). We will then explore what to release from the present, what to amplify from the emerging future, and what to hold onto as essential in order to build the bridge from today into their preferred future (Horizon 2).
1:00 – 1:30 PM | Lunch & Farewell
Join Your Peers
Erin Andrews, Quest Montessori School
Susan Angelides, Cambridge Montessori School
Bridget Barrett-Parker, Oak Meadow Montessori
Jon Bartlett, Brookwood School
Tim Belk, Boston Trinity Academy
Beth Black, Wellan Montessori School
Brian Bloomfield, Lyndon Institute
Derek Boonisar, The Fenn School
Jennifer Borman, Commonwealth School
Michael Bowler, Harborlight Montessori
Katherine Bradley, Dana Hall School
Neal Brown, Inly School
Gabe Burnstein, Charles River School
Jeffrey Burroughs, Lincoln Academy
Charles E. Carter, Jr., Beacon Academy
Marshall Carter, Atrium School
Lise Charlier, The Cambridge School of Weston
Andrew Chappell, The Derryfield School
Emily Charton, The Rashi School
Elizabeth Clayton, Sant Bani School
Will Crissman, Tenacre Country Day School
Ryan Dahlem, The Rivers School
Meredith deChabert, The Gordon School
Jon Deveaux, Campus School of Smith College
Sean Duncan, The Winchendon School
Scott Erickson, Berwick Academy
Todd Eveleth, Tower School
Gretchen Forsyth, Glen Urquhart School
Patricia Gray, Jackson Walnut Park School
Renee Greenfield, Carroll School
arvind grover, Meadowbook School of Weston
Judy Guild, Brimmer and May School
Carla Haith, Mother Caroline Academy
Catherine Hall, Noble and Greenough School
Brian Hargrove, Northfield Mount Hermon
Danielle Heard, Nashoba Brooks School
Brooke Hopkins, Riverbend School
Colin Igoe, Long Trail School
Ben Jackson, North Yarmouth Academy
Timothy Johnson, Pingree School
John Kalapos, Buxton School
Tracy Keller, Green Mountain Valley School
Moira Kelly, EXPLO
Kristy Kerin, Brewster Academy
Chris Kolovos, Boston University Academy
Walter Landberg, St. Michael’s Country Day School
Brendan Largay, Belmont Day School
Gretchen Larkin, Eagle Hill School
Sophie Lau, Lincoln School
Meredith Legg, The Winsor School
Maggie Lyon, Breakwater Learning
Molly MacKean, Kents Hill School
Rod MacNeal, Jr., The Chestnut Hill School
Alex Magay, The Woodward School
Scott Mattoon, The Sage School
Rhiannon McElwee, Lesley Ellis School
Rene Menard, Thornton Academy
Emily Miller, Nantucket Lighthouse School
Grainne Murray, Bay Farm Montessori Academy
Tara Nemeth, The Bay School
Tim Newbold, The Village School of North Bennington
Kathleen Nicholson, Wolfeboro Camp School
Daniel O’Brien, The Putney School
Barbara Orlowitz, Andover School of Montessori
Garine Palandjian, St. Stephens Armenian Elementary School
Sarah Parker, Meridian Academy
Michael Peller, Vermont Academy
Sarah Pelmas, Beaver Country Day School
David Perry, Falmouth Academy
Nick Perry, The Grammar School
Heather Pinedo-Burns, Acera School
Timothy J. Powers, Pinkerton Academy
Kimberly Ridley, Fayerweather Street School
Sam Schaffer, The Roxbury Latin School
John Schatz, The Academy at Charlemont
Margaret Schlachter, The Mountain School at Winhall
Mike Schloat, The Bement School
Greg Schneider, Belmont Hill School
Arnold Shorey, Foxcroft Academy
Daniel Skoglund, Maple Street School
Sergio Simunovic, The Greenwood School
Tao Smith, Gould Academy
Amy Smucker, Proctor Academy
Jamie Soule, Erskine Academy
Camillo Spirito, Rock Point School
Mark Stanek, Shady Hill School
Brendan Sullivan, St. Sebastian’s School
Elisabeth Swain, Touchstone Community School
Honor Taft, The Pike School
Mark Tashjian, Burr and Burton Academy
Karen Thomson, Red Fox Community School
David Tinagero, St. Andrew’s School (RI)
Katherine Titus, Moses Brown School
Jessie Vogel, North Shore Nursery School
Mary Warner, Berkshire Country Day School
Emily Waterfield, The Common School
Susanna Waters, Fay School
Allison Webster, Dedham Country Day School
Daniel Welch, George Stevens Academy
Joe Williams, New Hampton School
Grace Yannakakis, Shrewsbury Montessori School
Scott Young, The Park School
Pete Zetlan, The Cornerstone School
Thank you to our Sponsors
Cancellation Policy
Cancellations and transfer requests must be sent via email to info@aisne.org. Cancellations received up to 10 days before the start of the event will receive a 100% refund, less a $150 administrative fee. This fee covers the cost of our minimum commitments with our hotel partners; thank you for your understanding. Transfers of registrations from one person to another are permitted up to 3 business days before the start of the event.
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