On The Way To School

In today’s episode of On The Way To School, I’m digging into a question that deserves more attention in independent schools:
Are we looking at student retention from the wrong direction?
Research on faculty belonging and retention points to something we already know intuitively: educators are more likely to stay when they experience a healthy workplace culture, manageable workloads, meaningful relationships, and a genuine sense of belonging.
And that matters for students.
When teachers feel supported, they have more capacity to do the thing that matters most—build relationships with students.
A teacher who knows a student.A teacher who notices when something changes.A teacher who cares.A teacher who makes a student feel like they belong.
That relationship can shape engagement, belonging, and ultimately whether a student wants to remain in a school community.
So maybe retention isn't simply an enrollment strategy.
Maybe retention is a people strategy.
Support your teachers. Improve their experience. Protect their capacity to teach well. Then pay attention to what happens for students.
And one more reminder for school leaders: use the research.
Our stories and experiences matter. Data matters. But there are scholars studying these exact questions, and their work can help us test what we think we know.
🎙️ On The Way To School🎧 Listen to the latest episode wherever you get your podcasts.
#OnTheWayToSchool #TeacherRetention #StudentRetention #FacultyBelonging #SchoolLeadership #IndependentSchools #EducationLeadership #SchoolCulture #TeacherWellbeing #EducationalLeadership #StudentBelonging #Research

Today on On The Way To School, I’m talking about the start of a new school year—and the opportunity it creates for educators and administrators to recast your own vision.
We spend so much time thinking about what students need when they return: new classrooms, new teachers, new routines, new friendships.
But what about us?
Who are you excited to reconnect with?Who is someone you don’t know well enough yet?What relationships could you intentionally build this year?What opportunities could you volunteer for?What do you want people to know about your interests, your skills, and where you hope your career is headed?
The beginning of the year is a chance to expand your sphere of influence—not just by working harder, but by being more intentional about where you spend your time and who you build relationships with.
And for parents: be an advisor before you become an advocate.
When your child comes home saying a friendship has changed, resist the urge to immediately call another parent or solve it for them. The first week of school is a time for kids to navigate new relationships, make room for new classmates, and develop the skills to solve some of their own problems.
Give them advice. Give them space. Let them grow.
And finally—remember that the first week is a marathon. Get some sleep. Keep your evenings simple.
The school year is officially underway. Make it a good one.
🎙️ On The Way To School🎧 Listen to the latest episode wherever you get your podcasts.
#OnTheWayToSchool #SchoolLeadership #EducationLeadership #IndependentSchools #Educators #SchoolCulture #Leadership #Parenting #StudentLife #ProfessionalGrowth #Education

It’s Monday, and On The Way To School is back in school mode.
In today’s episode, I’m looking at a recent development from the U.S. Department of Education’s Office for Civil Rights and what it may mean for independent school leaders and board committees working on equity, belonging, and discipline.
The bigger leadership lesson, though, goes beyond any one letter or policy:
When the rules change, don’t react first. Interpret first.
If your board has committees focused on equity, belonging, diversity, student life, or governance, this is the moment to ask:
• What does this mean for our existing policies?• What does it mean for our strategic goals?• Who is responsible for interpreting the guidance?• How does it align with our mission and bylaws?• Do we need counsel to help us understand the implications?
The temptation is to let one person read something, make an interpretation, and immediately turn that interpretation into practice.
That’s governance by assumption.
Good governance requires us to slow down enough to understand what has actually changed—and what hasn't.
Know your policies. Know your bylaws. Know your mission. Know when to bring in counsel.
Because in school governance, the details matter.
🎙️ On The Way To School🎧 Listen to today’s episode wherever you get your podcasts.
#OnTheWayToSchool #SchoolGovernance #IndependentSchools #EducationLeadership #SchoolLeadership #BoardGovernance #IndependentSchoolLeadership #EducationalLeadership #SchoolBoards #Governance

Dr. Chris Dennis opens the episode with warm-weather updates and a heartfelt response to the devastating flooding in Nepal, noting how technology amplifies shared empathy. He reflects on a moving faculty and staff Eucharist that affirmed the school’s Episcopal identity and its quiet but powerful role in community life.The episode also celebrates the start of the school year—ninth-grade trips, chaperones, and the return of routines—while urging listeners to show appreciation and grace for educators as they head back into the classroom. It closes with a light, human moment about the heat and a cup of coffee before the host hits the road.

When did you first feel like you belonged?
That question changed the conversation for me.
In today’s episode of On The Way To School, I’m reflecting on a question that came up during my recent Lonely Graduation book conversation on Martha’s Vineyard:
When did you first realize you were special?
For me, the answer came much later than I expected. It wasn’t until my 30s that I fully recognized my unique gifts and understood that I had a responsibility to steward them well.
But then my fellow panelist Connie asked a different question:
When did you first feel like you belonged?
And that question opened up an entirely different conversation.
Because knowing you’re special is personal. Belonging is relational.
You can know your gifts, understand your purpose, and still find yourself in a community where you don’t feel seen, valued, or connected.
So as we begin another school year, I’m asking educators and leaders to consider:
Do you feel like you belong in your current role—not just on the org chart, but in the community?
If the answer is no, don't ignore it.
Belonging can be the difference between showing up from obligation and showing up with purpose. It can help us sustain ourselves when the work gets difficult and the cup starts to feel empty.
And sometimes, finding belonging starts with one honest question.
🎙️ On The Way To School🎧 Listen to the latest episode wherever you get your podcasts.
#OnTheWayToSchool #LonelyGraduation #Belonging #SchoolLeadership #EducationLeadership #IndependentSchools #WorkplaceCulture #Leadership #Educators #Purpose #Community

Today on On The Way To School, I’m talking about one of the biggest tensions I’m noticing as educators and leaders increasingly use AI:
The output can move faster than our thinking.
AI can help us research, organize, synthesize, build presentations, and get to a finished product in minutes. That productivity is real.
But sometimes the time we save is actually thinking time—the time we need to wrestle with an idea, develop an argument, notice nuance, and actually know what we’re putting in front of other people.
I experienced this myself recently. AI helped me organize something I was working on, but when I got into the meeting, I had to reorient myself to the structure and argument. I knew the content—but I hadn't necessarily built it in the same way I would have if I had done every step myself.
So maybe the question isn't whether we should use AI.
It's whether we're using it in a way that preserves our own command of the work.
Sometimes the best AI workflow is:
Use it. Step away. Think. Come back. Edit. Simplify. Own it.
And please—if AI gives you 30 slides when you needed 10, don't blame the AI. 😂
🎙️ On The Way To School🎧 Listen to the latest episode wherever you get your podcasts.
#OnTheWayToSchool #AIinEducation #ArtificialIntelligence #EducationLeadership #SchoolLeadership #EdTech #AIforEducators #IndependentSchools #Leadership #FutureOfEducation

When leadership gets thorny, go back to the policy.
In today’s episode of On The Way to School, I’m talking about an increasingly important reality for school leaders: sometimes the hardest leadership moments are the ones you never planned for.
Unplanned head-of-school transitions. Student incidents. Enrollment challenges. Family demands. Community pressure.
When the temperature rises, it can be tempting to become defensive, avoid the conflict, or simply hope the situation blows over.
But strong leadership requires something else:
Be policy-focused. Be clear. Communicate. Document.
Families deserve to be heard—even when the answer is no.
And leaders have to be able to disagree, decline requests, and make difficult decisions without compromising their own dignity or the dignity of others.
You may not be able to control how people respond to a decision. You can control whether your process is thoughtful, consistent, documented, and aligned with the policies and responsibilities entrusted to you.
Because what feels resolved today can resurface six weeks from now in a very different form.
As we head into the new school year, it’s time to stop basking in the summer glow and get focused.
🎙️ On The Way to School🎧 Listen to today’s episode wherever you get your podcasts.
#OnTheWayToSchool #SchoolLeadership #IndependentSchools #HeadOfSchool #EducationLeadership #SchoolGovernance #Leadership #IndependentSchoolLeadership #EducationalLeadership #NonprofitLeadership

Healthy Boards. Healthy Schools.
We’re back. 🎙️ After a brief summer pause—and a great book conversation on Martha’s Vineyard—On The Way to School is back in gear.
In today’s episode, I’m digging into one of the most consequential relationships in independent schools: the board–head partnership.
Recent stories about schools facing serious fiduciary challenges, trustees being named in litigation, and the growing focus on supporting new heads of school all point to the same reality:
Healthy schools require healthy boards.
So what does a healthy board actually look like?
🔹 Trustees who understand their fiduciary responsibilities🔹 Committees working toward meaningful goals—not simply giving reports🔹 Board members who understand the bylaws and their role🔹 A culture where governance is bigger than personalities and individual agendas🔹 Regular opportunities to assess whether trustees feel informed, engaged, and effectively utilized🔹 A strong, trusting partnership between the board and head of school
And if you're thinking about serving on a school board, don't underestimate what you bring to the table. Retired educators, business leaders, community members, and parents can all bring valuable expertise and perspective to the fiduciary work of sustaining a school.
The forecast is clear: healthy boards are healthy schools.
🎙️ Listen to the latest episode of On The Way to School wherever you get your podcasts.
#OnTheWayToSchool #SchoolGovernance #IndependentSchools #BoardGovernance #BoardLeadership #HeadOfSchool #EducationLeadership #IndependentSchoolLeadership #NonprofitGovernance #SchoolBoards

Sometimes the most powerful response is no response at all.
In this episode of On The Way to School, I’m talking about what happens when we’re triggered in difficult working relationships—and why we often need to process before we respond.
A simple practice has stayed with me for years: write it down before you say it.
Grab a notebook. A Post-it. A Google Doc. Write the sentence you want to say. Name what you’re feeling. Identify what you need. Then stay present.
Not everything requires your commentary. Not every moment requires a reaction. And sometimes, reacting too quickly means giving away the very power we’re trying to protect.
But those notes can also tell you something important. If the same frustrations keep showing up, with the same person or in the same dynamic, pay attention. There may be a deeper issue that needs to be addressed.
Process first. Respond second.
🎙️ On The Way To School🎧 Listen to the latest episode wherever you get your podcasts.
And if you’re on Martha’s Vineyard next week, come join me on Tuesday, August 18, from 12–2:30 at the Martha’s Vineyard Museum for a conversation about Lonely Graduation: And the Journey After the Milestone.
#OnTheWayToSchool #SchoolLeadership #Leadership #EducationLeadership #EmotionalIntelligence #Relationships #SelfLeadership #IndependentSchools #LonelyGraduation

Dr. Chris Dennis returns for season nine with reflections on stepping back, recalibrating, and reclaiming joy by becoming a "tourist" in your own life and school. He shares the importance of revisiting what originally inspired you and highlights the launch of Jabali Academy as a source of community inspiration.Tune in for a short, uplifting episode about renewing purpose, supporting new educational ventures, and embracing small practices that bring freshness back into daily work.