On The Way To School

On today’s episode of On The Way To School, I’m thinking about what happens when significant changes are happening around our schools—and why thoughtful governance, legal guidance, and practitioner voice matter more than ever.
With proposed IRS and Treasury changes affecting tax-exempt organizations on the horizon, independent school leaders are asking important questions about compliance, governance, and how to protect their institutional mission.
My advice?
Have a plan.
Before putting anything into motion, understand what you’re trying to accomplish, build your approach, and—most importantly—talk to your counsel. Legal counsel is there to help schools navigate moments like this thoughtfully and responsibly.
But there’s another piece of this conversation that I think we can’t overlook:
Research.
Independent schools need more peer-reviewed scholarship that documents what practitioners, administrators, faculty, and boards are actually experiencing.
We need to document this moment.
We need to capture the decisions being made, the challenges schools are facing, and the lessons we’re learning along the way.
Because when the voice of practitioners—and the scholarship that captures their experiences—is missing, we lose context. We lose history. And we risk repeating the same challenges in the future.
My own doctoral research began with that same idea: when there’s a gap in the literature, sometimes the responsibility is to help fill it.
So as independent schools navigate this moment, let’s not just react to what’s happening.
Let’s document it. Study it. Learn from it. And help shape what comes next.
🎧 Listen to today’s episode of On The Way To School wherever you get your podcasts.
#OnTheWayToSchool #SchoolLeadership #EducationalLeadership #SchoolGovernance #IndependentSchools #SchoolBoards #EducationLeadership #EducationalResearch #SchoolGovernance #IndependentSchoolLeadership #NonprofitLeadership #SchoolCulture

Dr. Chris Dennis discusses the hectic back-to-school season, the importance of honoring families' commitments to independent schools, and supporting teachers during long evening events. He emphasizes treating parents as partners and the value of community connections.He also shares insights from his equity, justice, and leadership class about changing political rules of engagement and invites community experts into the classroom. Practical tips for engaging at school events and connecting with new people round out the episode.

On today’s episode of On The Way To School, I’m thinking about resilience, independence, and what happens when we remove the structures that have surrounded our students for most of their lives.
We want our kids to be successful. So we organize. We supervise. We intervene. We advocate.
And often, we should.
But there are also moments when students need to experience some productive tension—to figure something out, try something new, navigate a difficult social moment, or simply sit with the discomfort of not knowing what comes next.
That can be especially hard when students leave home for college.
Suddenly, the scaffolds are different. The social structures are different. And they have to begin developing the skills to create community for themselves.
That doesn't mean we stop listening.
It doesn't mean we ignore real struggle.
It means we learn to distinguish between supporting a student and solving the problem for them.
Because sometimes there really is nothing we can do.
They need the experience.
They need the reps.
And you don't get the reps without giving students enough room to take some healthy risks, make mistakes, and discover that they can handle more than they thought.
🎧 Listen to today’s episode of On The Way To School wherever you get your podcasts.
#OnTheWayToSchool #SchoolLeadership #Parenting #StudentDevelopment #Resilience #CollegeTransition #EducationalLeadership #StudentBelonging #Independence #SchoolCulture #Education

In this episode Dr. Chris Dennis explains the Treasury/IRS proposal to strip 501(c)(3) status from private schools that use race-conscious policies in admissions, scholarships, athletics, or programming, and outlines the potential effects on up to 18,000 institutions.He offers practical guidance for school leaders — inventory programs, align boards, prepare public comments, and communicate plans to employees and families — and warns about the secondary impact on charitable deductibility and fundraising.

On today’s episode of On The Way To School, I’m thinking about what happens during those first few days when new faculty are learning a school’s culture in real time.
They’re learning the policies.They’re learning the cues.They’re figuring out where there’s flexibility—and where there isn’t.
And they’re wondering: “Am I doing this right?”
That’s why the first couple of weeks are so important.
Don’t wait two weeks for the formal check-in. Walk by. Say hello. Ask how the day is going. Give them a place to process the small things that can feel enormous when you’re brand new.
And remind them: you don’t have to be perfect on day one.
You’re building reps.
For school leaders, sometimes the most meaningful support isn’t another meeting, another document, or another evaluation.
Sometimes, it’s simply being present.
Give your new faculty some love. They’re not just learning how to teach at your school.
They’re learning how to belong there.
🎧 Listen to today’s episode of On The Way To School wherever you get your podcasts.
#OnTheWayToSchool #SchoolLeadership #EducationalLeadership #NewFaculty #TeacherSupport #FacultyCulture #IndependentSchools #SchoolCulture #TeacherRetention #EducationLeadership
If you want, I can also make this more punchy/Instagram-native or more executive/thought-leadership oriented.

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