On The Way To School

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.

Dr. Chris Dennis walks through how school leaders can prepare in August to launch a steady school year: setting meeting cadences for direct reports, prioritizing classroom time (his goal is 25%), and staying present with faculty, students, and families.He shares practical tips—short classroom visits that aren’t evaluations, morning drop-off greetings, balancing teaching and advising, and building a consistent schedule that absorbs inevitable crises—so you start the year ready to lead.

Dr. Chris Dennis delivers a short drop-in episode on why equity work must be embedded in school board governance rather than treated as an add-on.He outlines practical steps—linking equity priorities to accreditation and core board functions—to make DEI durable, and offers to share resources for trustees ready to operationalize this work.

On the Way to School with Dr. Chris Dennis closes out May with a heartfelt message celebrating educators and administrators for making it to the final week, reflecting on a holiday of remembrance and a sermon about the price of success.Chris highlights that success often comes from mundane, daily commitments—showing up, persevering, and honoring small acts of dedication—and urges listeners to affirm and celebrate the work they’ve done this year.

Dr. Chris Dennis opens this episode with Memorial Day reflections, honoring those who served while sharing a lighthearted community story about an epic Continuous Uno game.He then shifts to school leadership advice: use the quiet review week to plan and prepare for a productive summer so your fall can be calm and focused. Finish May strong and take time to rest and appreciate your community.

In this episode Dr. Chris Dennis discusses a Forbes article outlining five signs a leader may need executive coaching—tolerating visible low performers, high performers burning out or quitting, lack of promotions, defensiveness when challenged, and teams afraid to speak the truth.He explains how coaching supports better change management, accountability, and retention, and encourages educators to identify trusted executive coaches to support their leaders.