Monday, January 27

Arrive and Settle In

Monday arrival is especially recommended if you will be participating in Tuesday morning programming.

4:00 - 6:00 p.m.
Check into Ocean Edge

7:00 - 8:30 p.m.
Networking Dinner at The Beacon Room in Orleans (advance RSVP required, please email Betsy at

9:00 p.m.
Drinks and Conversation Back at Ocean Edge at Bazyo's Pub

Tuesday, January 28


8:00 - 9:00 a.m.

AISNE Board Meeting

9:00 a.m. - 12:00 p.m.
AISNE Board members only

Peer Group Meetings

9:00 a.m. - 12:00 p.m.
Peer Group Meetings by Personal Leadership Stage

  • 1st Time Heads of School: Being new to independent school headship is a special benchmark in your career. Be supported and make new connections in this cohort.
  • 2nd - 5th Year Heads of School: The “honeymoon” is over, the initial goals set and addressed. What’s next? Join this cohort.
  • 6+ Year Heads of School: You’re seasoned in headship. Connect with peers as part of this cohort.

Retreat Opening / Welcome Activities

11:00 a.m. - 2:00 p.m.
Boston Chair Massage by Ticketed Appointment:
Sign-Up When You Check in at Ocean Edge

Sponsored by:

12:00 - 1:00 p.m.
Networking Lunch

11:00 - 2:00 p.m.
Snowy Owl Specialty Coffee Cart

Sponsored by:

Official Retreat Kickoff

Strategy Tracks

1:00 - 1:45 p.m.


2:00 p.m.
Claire Leheny, AISNE

Opening Session

2:15 - 4:45 p.m.
Clouds or Witnesses?
Leadership Opportunities to Resolve Racial Stress in Independent Schools
Howard Stevenson

To what extent do you currently position diversity, equity and inclusion at the core of your leadership? This working session will help you develop your social justice warrior role as a head of school. Turn values into actions and work collaboratively with your peers to identify personal action items to bring back to your work on campus. Dr. Stevenson will help each attendee walk the talk of social justice and racial equity.

Annual Association Meeting

5:00 - 5:45 p.m.

Dinner and Networking

6:15 - 7:00 p.m.
Cocktail Hour

7:00 - 8:30 p.m.

Lead Dinner Sponsor:

Dinner is Also Generously Sponsored by:


8:30 - 10:00 p.m.
Drinks at Ocean Edge at Bayzo's Pub

Wednesday, January 29

Retreat Activities

6:00 - 9:00 a.m.
Boston Chair Massage by Ticketed Appointment:
Sign-Up When You Check in at Ocean Edge

7:00 - 8:00 a.m.

  • Cycle
  • Take Photographs
  • Walk on the Beach
  • Practice Yoga

7:45 - 8:45 a.m.
Networking Breakfast

7:00 - 9:00 a.m.
Snowy Owl Specialty Coffee Cart

Sponsored by:

Morning Keynote Address

9:00 - 10:00 a.m.
Leveraging Strengths and Embracing Change
Katie Conboy, Simmons University

During Provost Katie Conboy's tenure at Simmons, the institution has experienced transformational change. Katie will share how she and the leadership team have:

  • overhauled their curriculum
  • rebranded the campus experience
  • maximized existing infrastructure

Provost Conboy will also explore how the institution-wide strategic planning process she led has set Simmons on course for a bright future.

Retreat Presentations and Facilitated Conversations

10:15 - 11:30 a.m. -- Choose One

Goal-Setting for a New Landscape: What Heads Must Know to Lead Transformative Fundraising Efforts | Allison White, Senior Vice President, Graham-Pelton

Without carefully considered and strategic resourcing, it is difficult to meet your fundraising objectives. But what should that look like? What happens when the appropriate investment does not take place? This talk will review the critical success factors that affect all fundraising efforts with a special focus on cultivating a high-performing board and staff, planning ahead for expected spend, and the ways to consider and evaluate the return on your investment.

Refining Your Message: What Sets Your School Apart and Makes It Unique | Maria LaTour Kadison, President & CEO, EdwardsCo

Understand how to use data to inform your decision making, refine your messages, and define your brand. In today’s independent school market, it is essential for schools to continuously work to understand what sets them apart and what makes them unique. Use this time to evaluate where your school is in this ongoing work and what steps you should take within your school community to strengthen your brand and maximize enrollment and retention.

Understand Your School's Community to Inform Smart Decision Making | Michael Moon

Your school's community has the potential to be a rich source of valuable ideas and feedback, influencing major decisions which will shape the lives of people both inside and outside of your walls. How do you assess the needs of all stakeholders, ensuring they feel heard and their needs are being met? Dr. Moon will stretch us to think about new ways in which data can play a role in making more effective decisions about people and people practices. How do we go about getting this data, analyzing and converting it into insights to help us shape questions we want to ask members of our faculty and staff? This workshop will provide actionable items and next steps.

Town, Gown & a Jury Trial: Lessons Learned | Sara Goldsmith Schwartz, Schwartz Hannum PC

Experienced school counsel, Sara Goldsmith Schwartz will facilitate a lively and interactive conversation about successfully navigating complex and challenging legal issues raised by an employee boundary crossing that resulted in a jury trial and criminal prosecution. Using a case study approach, be engaged in a discussion about strategies for responding to criminal investigations into the alleged misconduct of current employees. Learn tips and traps for when and how to appropriately terminate an employment relationship with an accused employee; how to manage communications with your school community and the press regarding criminal prosecution of an employee; and how to effectively protect the institution while working collaboratively with local authorities in the context of a criminal investigation, prosecution and jury trial.

Create a Data-Informed Culture to Support Sustainable Decision Making | Gary Esposito, Director of Operations, The Wheeler School, Gautam Sundarum, Practice Leader Urban Design, Associate Principal, Brooke Trivas, Practice Leader K-12, Principal, Perkins and Will

Independent schools aim to prepare students for future success through rigorous and intentional academic programs, allow pursuit of individual interests, and supporting project-based learning. In order to achieve these goals, it is critical that the physical learning environment reflect its unique academic pedagogy and is grounded within financial realities. School administrators and designers can work together to develop these learning environments by examining facilities at a campus-wide scale. Featuring The Wheeler School as a case study, speakers will outline a data-driven approach to master planning that examines utilization, efficiency, programming and ideal adjacencies. An analytical process helps designers develop a principle-driven framework plan that is responsive, facilitates decision-making in the short term and long term vision, and offers incremental and achievable moves that serve their client’s long-term vision. The process enables schools to develop a holistic understanding of campus needs and work towards a phased implementation and investment strategy. It also avoids taking on new building projects without clear reason.

Cultivate and Meet the Needs of Your Diverse Leadership Team | Noni Thomas López, Gordon School

As head of school, you know the value of having a great team and the important role that strong teams play in building positive school culture. But how much time do you actually spend intentionally cultivating your "first team," particularly those members from historically marginalized groups? Participate in a conversation about how heads may bring out the best in their teams and, in doing so, foster cultures where all community members feel a sense of ownership and responsibility for their school's success.

Midday Keynote Address

11:40 a.m. - 12:40 p.m.
The Privileged Poor
Tony Jack

In The Privileged Poor, Tony Jack reveals that the struggles of less privileged students continue long after they’ve arrived on campus. Admission, they quickly learn, is not the same as acceptance. His bracing and necessary book documents how school policies and cultures can exacerbate preexisting inequalities and reveals why these policies hit some students harder than others.

If we truly want our schools to be engines of opportunity for all, our policies and cultures must change. Tony provides concrete advice to help schools reduce these hidden disadvantages — advice we cannot afford to ignore.


12:40 - 12:55 p.m.
Pick-Up Lunch on Your Way to Your Next Conversation

Retreat Presentations and Facilitated Conversations

1:00 - 1:45 p.m. -- Choose One

Move from Instability to Stability: Bold Leadership in Anxious Times | Diane Rich, Rocky Hill Country Day School

The transition to a new head of school always requires adaptability on the part of both the school community and the head. Many new heads enter unstable systems or perhaps even ones in crisis. Assuming leadership during periods of uncertainty poses particular sets of challenges. How do you as leader make bold decisions to move your institution forward while also helping your community manage anxiety and get comfortable with ambiguity, in order to come out the other side of change stronger and more confident than before? Join me in a discussion of systems thinking and managing leadership challenges.

Complexities and Opportunities of Internal Hires | Derek Boonisar, The Fenn School

Being a member of an independent school community often resembles an intricately woven web. Join Derek Boonisar, an internal head hire, in a discussion about ways you can cultivate leadership from within your community and the complexities and opportunities this presents to you as a head of school. The tension between wanting to bring in fresh ideas and new hires with the desire to also retain members of your faculty and staff who are hoping for growth opportunities and new challenges. As a head of school, how do you balance creating and fostering internal leadership opportunities with the need to look externally for that next hire?

Single-Gender School Identities | Katie Conboy, Simmons University

Explore what it means to be a single-gender school within the independent school community while also embracing gender equality and celebrating diversity and inclusion. Discuss how a school is able to have a strong tradition of empowering a single-gender while challenging traditional gender roles and being inclusive throughout the school community from the initial application process through graduation day and beyond. Take this opportunity to discuss with your peers how traditional notions of gender are evolving, as increasingly, individuals do not conform to the gender binary.

Tools for Schools Enrolling Disadvantaged Students: The Data Behind Diversity | Tony Jack

Dig deeper into what makes lower-income undergraduates graduating from private high schools the "privileged poor". Discuss what experiences and tools our school communities can provide to our students who come from more disadvantaged backgrounds. Identify systems and structures in our school communities to help these students access institutional resources, social networks, and informal social rules that govern elite academic institutions.

Preventing and Managing High-Stakes Litigation: Lesson, Tips and Traps | Sara Goldsmith Schwartz, Schwartz Hannum PC and Rob Gustavson, Fay School

Join experienced school counsel, Sara Schwartz, and Fay School Head, Rob Gustavson for a lively, interactive session about lessons learned by successfully prevailing through a multi-year federal court litigation involving a student’s alleged “Wi-Fi allergy.” Utilizing a case study approach, learn strategies for preventing (and prevailing through) litigation, whether based on challenging student / family complaints, alleged environmental hazards, demands for ADA accommodations or alleged violations of the student handbook. Hear tips and traps for fostering collaborative approaches among your board, head and counsel to achieve effective risk management.

Hitting the Mark with Students Hailing from Marginalized Backgrounds | Sarah Smith, Dean of Students and Eric Nett, Dean of Alumni, Placement & Enrollment, Beacon Academy

Engage in an informative and solution-oriented presentation of school strategies that holistically support low-income students and their families. Gain new insights about common institutional gaps in academic and financial support as well as best practices for developing potential solutions for your school. Student case studies will be provided, as a basis for meaningful conversations.

Reflections and Retreat Farewell

1:45 - 2:00 p.m.