"Never let a child risk failure until he has a reasonable chance of success."
     - Maria Montessori

Heads of School Retreat

MSM Heads of School Retreat, November 29-30, 2018

Leadership of schools in changing times is fraught with opportunities and challenges. Leaders are expected to manage competing interests, to create conditions which form the foundation for lifelong learning, to sustain the motivation and morale of staff and to raise achievement levels of all students. Leading a school is one of the most rewarding and the most challenging vocations in academia. It can also be one of the loneliest. A head of school engages every day with many constituents – students, parents, board members, donors, faculty, staff, and community members – but it is difficult to find a colleague or two who understands the role, who can truly offer a listening ear, and who can offer a helpful, unbiased response. Finding a peer group that can offer support and suggestions in a safe environment is essential to thriving in the role.

Based on feedback from our member survey, and our desire to help meet the needs of member schools, MSM will be hosting a two-day retreat for heads of school. Your financial investment is small considering the large number of opportunities that could be gained.

Would you like to spend a couple of days talking with peers about admissions, marketing, budgeting, legal issues, or board relations? Would you look forward to trying out a few ideas with people that understand your job? Would you welcome the chance to learn from others who are engaged in the same efforts? This is your chance!

Leading Through Changing Times

The past 30 years have seen more changes to the way in which school education is structured, implemented, and evaluated than in the previous hundred years since education in most western societies became compulsory. Through all this change, increasing responsibilities have been placed on school leaders.

Leadership of schools in changing times is fraught with opportunities and challenges. Leaders are expected to manage competing interests, to create conditions which form the foundation for lifelong learning, to sustain the motivation and morale of staff and to raise achievement levels of all students.

Featured Workshops

The Vulnerability of Teaching and Learning in a Selifie Society

Join us to explore the generative power of vulnerabilities facing individuals who inhabit educational spaces. We will discuss that vulnerability can be an asset in developing understandings of others, and in interrogating the self. Explorations of vulnerability offer a path to building empathy and creating engaged generosity within a community of dissensus. This kind of self-examination is essential in a selfie society in which democratic participation often devolves into neoliberal silos of discourse and marginalization of others who look, think, and believe differently.

This workshop will be presented by Dr. Diane Foucar-Szocki, professor from James Madison University.

Gender, Sexuality, and Diversity Through a Developmental Lense

In this workshop we will look at a framework and language that offers our schools a dynamic, research-based platform for designing developmentally appropriate curriculum and instruction.

This session will be guided by Dr. Jennifer Bryan, Dircetor of Team Finch Consultants.


There are currently 80 million Millennials in the U.S. – nearly one-fourth of the total population. With an annual buying power of $200 billion, they are the most lucrative market. Plain and simple: Nearly every marketer today is making Generation Y a priority – or at least working to understand what drives and delights this instrumental group.

One key element that justifies Millennial domination of the marketplace is the fact they respond to a brand new marketing style. Here, we'll discuss important tactics for marketing to the demographic of the hour and explain why these tactics are lasting ones.

Join Donna Milani Luther, Head of School of the Inly School, for a discussion about changing trends, challenging times, and marketing to millennials.about marketing.

NIghtime Entertainment

Unplug those gadgets, turn off the cell phones, and spend some quality time reaxing!

Sharing Our Stories

Come prepared to tell a peer about a specific leadership issue you are facing. We will validate each other's stories of challenge and share wisdom about change.

Conference Schedule

November 29, 2018
9:15 = Registration opens
10:00 = Welcome
10:15 = The Vulnerabilty of Teaching and Learning in a Selfie Society
12:00 = Lunch
1:30 = Gender, Sexuality and Diversity with a Developmental Lens
3:30 = Break
5:00 = Cocktail hour
6:00 = Dinner
7:30 = After dinner activity

November 30, 2018
8:00 = Breakfast
9:00 = Marketing to Millenials
10:00 = Break
10:30 = Sharing Our Stories
12:00 = Lunch

Conference Packages and Fees

Conference packages include overnight accommodations, meals, conference materials, sessions led by knowledgeable experts, cocktail hour, and networking opportunities.

Cost for MSM Member Schools is $350 per person. Cost for NON Member Schools is $400 per person.

Staying at the facility is not required but there is no discount available for attendees that will not be lodging overnight.

Registration closes on October 25, 2018.

Extended stay option available!

For those traveling from a distance, or who just want a relaxing get-a-way, we are also taking reservations for rooms on Wednesday, November 28 and Friday, November 30. Rooms are available for $166.43 per night and can be reserved when you register for the conference.


Freedom to meet... and retreat at a quintessenial Cape Cod resort. The Ocean Edge Resort and Golf Club was voted Best Resort Cape Cod in Boston magazine's 2017 Best of Boston Awards. Ocean Edge Resort is the perfect venue for busy Heads of School to be productive and successful while ensuring fun and relaxation along with the luxury amenities of a first-class resort.

This property is a 5-minute walk from the beach. Located in Brewster, this resort features a Nicklaus Design golf course. The resort features 5 pools, a 26.1 miless bike trail, 11 tennis courts and rooms furnished with Cape Cod décor. Lessons are available and include golf, tennis and exercise classes.

The Ocean Edge Resort & Golf Club offers the Ocean Terrace Restaurant with views of Cape Cod Bay. Bayzo's Pub is decorated like an English Tavern with live music on the summer weekends. Other dining options include grilled dishes, burgers, cocktails and ice cream.

Nickerson State Park is 5.3 mi from the The Villages at Ocean Edge Resort & Golf Club. Crosby Beach is 1.3 mi away.


Registration has closed.