EXPLO Elevate shares good ideas, practices, and wisdom to help schools and their communities flourish.
Dear Friend,
I spent a wonderful weekend with a group of educational administrators most of whom are early in their leadership careers. I like working with early career leaders because it gives me an opportunity to share knowledge, principles, and frameworks that have proven helpful to me over the years – things I wish I really understood or could have articulated better earlier in my own career. The application of Occam’s Razor. Chesterton’s Fence. The Map is Not the Territory. Discerning the difference between signal and noise, something I like to refer to as “the perils of ‘big ears.’” The duty of loyalty. Productive conflict. Knowing what success looks like but also using inversion to assess where things could go wrong so you can mitigate beforehand. Charlie Munger, a big fan of inversion thinking, is famous for saying, “All I want to know is where am I going to die so I’ll never go there.”
We’ve had quite a few reach outs from heads of schools and senior leaders these past couple of weeks. I chalk that up to spring break and actually having the time to disengage from the day to day, which then allowed for flying at a higher altitude, thinking bigger, and longer term. It’s been great having conversations about what could be possible at schools across the country and the steps necessary to get there.
Lessons from the Startup Frontier: Transforming Traditional Education
Getting a new school off the ground is never easy. Turning a former corporate site into a buzzing campus for a new boarding and day school intent on remaking education is a real challenge. Tom Woelper led this innovation journey as the founding head of New England Innovation Academy (NEIA). Now head of school at Cheshire Academy, Tom has distilled his insights from NEIA and how those can be applied to a 231 year old boarding school. We’re thrilled to share his article Lessons from the Startup Frontier: Transforming Traditional Education. (EXPLO Elevate was honored to work with NEIA from its launch back in 2020 and we’re thrilled that we’ll continue to work with Tom at Cheshire.)
Ross has been writing about progress cultures and the habits of becoming for schools. He’s added a new habit to the list: wellness thinking. It represents a shift in how we conceptualize school leadership and institutional health. While traditional metrics often focus on academic outcomes, capital improvements, or enrollment figures, this seventh habit acknowledges that a school's true vitality extends beyond measurable progress markers. By adopting wellness thinking, school leaders recognize that sustainable excellence requires not just building or fixing, but nurturing and maintaining what already exists. This approach invites leaders to step back from reactionary problem-solving and instead embrace stewardship that honors the humanity of all community members. In today's educational landscape, where burnout, anxiety, and external pressures increasingly threaten school ecosystems, this wellness perspective offers a timely counterbalance that can transform how we lead, support, and sustain our learning communities.
“No margin, no mission” was a phrase popularized by Sister Irene Kraus, former CEO of the Daughters of Charity Health System. Much as many of us don’t like to characterize schools as businesses, the ability of schools to sustain reasonable financial margins is what allows them to continue their impact. Yet, far too many schools have no idea what the margin is on any particular division, program, or activity. The reality is that the economics of schools are wrapped in a complex web of hidden cross subsidies. Once you start unwinding broad categories, you start to see that your school is studded with cost centers that contribute to overhead in dramatically different ways. Getting a handle on contribution to overhead is essential for any school that aims for financial health.
Every time I’m at an event where Irshad Manji speaks, I’m taken by her wisdom and expansive and nuanced framing of how living with paradox is the foundation of living a life of moral courage. After eight years of work, she’s now debuting a documentary for which she served as executive producer. The award-winning film, Mississippi Turning, is the story of Genesis Be who passionately opposes Mississippi’s flag because it features the Confederate battle emblem – a salute to slavery – while Louis McFall strongly supports the flag because he values home and heritage. Can each stand their ground and still create common ground? Join Irshad and Genesis for a virtual watch party on April 22. This may be a film you’ll want to bring to your school. Sign up for the watch party here.
Building Brave: A Conversation About Young People, Anxiety, and Resilience
Join me for a free webinar on April 10th where I'll be speaking with Meredith Elkins, Ph.D., Co-Program Director of the McLean Anxiety Mastery Program at McLean Hospital and faculty at Harvard Medical School. She will share practical knowledge and strategies for parents and educators to help young people manage anxiety and develop genuine emotional strength. I believe this will be a valuable resource for both families and faculty. Register here and spread the word!
Have a project brewing in the back of your mind? Let's chat. Even if it's just an initial thought, a quick call could help us explore possibilities you haven't considered. No pressure – just good thinking with colleagues who understand the independent school landscape. Check out our website for more on what we bring to the table.
Finally, the other day I was reminded of the power of exploring new places. David Torcoletti, EXPLO Elevate Senior Consultant, began his career as a fine arts photographer before diving into decades of work in independent schools. He’s still photographing and his current project has him exploring the cemeteries of the Boston area. He texted me from a cemetery in Pembroke, Massachusetts with a photo. He later called me and told me he tripped on a grave site and when he looked down he saw it was the grave of Harry MacGregor. The name didn’t ring any bells for either of us, but MacGregor’s work sure did. MacGregor was the songwriter known for The Red Red Robin Comes Bob Bob Bobbin’ Along, I’m Looking Over a Four Leaf Clover, Side by Side and Try a Little Tenderness. David and I had a great conversation about what we’d want to put on our headstones (no final decisions on that) and the delightfulness of being surprised.
Serendipity. I hope you make some room for it.
Moira
Join us
Join EXPLO Senior Consultant, David Torcoletti, where he will be a featured speaker at the Deans Roundtable Conference, June 23 - 26, 2025 at New England Innovation Academy.
EXPLO, 932 Washington Street, Norwood, MA 02062, USA, 781.762.7400
.png?upscale=true&width=520&upscale=true&name=Untitled%20design%20(14).png)
