On The Way To School
by Christopher S. Dennis
🎙️ On the Way to School: Six Minutes to Elevate Your Educator’s Day 🎙️ Embark on a transformative journey with On the Way to School, the essential podcast for educators and school administrators seeking to enrich their mornings with impactful insights. Each concise six-minute episode delivers powerful tips and strategies to empower your educational leadership and classroom effectiveness. What You’ll Discover: - Conflict Resolution: Master techniques to navigate and resolve classroom and administrative disputes smoothly. - Leadership Skills: Develop and refine your leadership qualities to inspire and guide your team and students. - Social Justice in Education: Explore actionable strategies to foster an inclusive and equitable learning environment. - Growth Mindset: Cultivate a resilient and positive mindset that encourages both personal and professional development. - Daily Motivation: Receive daily doses of inspiration to keep you energized and focused throughout the school day. Why Li
Episodes
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Season 10 Returns: Reset, Reflect, Reignite
We’re familiar, but we’re not connected. That thought has me reflecting on how we build relationships—not just with our students, but with the adults we work alongside every day. Welcome to Season 10 of On The Way To School! After taking a little time to reset and get the school year into rhythm,...
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Choosing Schools, Choosing Futures: When Parental Values Meet Reality
This morning on On The Way To School, I’m reflecting on a conversation we had last night at Lore Leimert Park about the continuum of care—and a powerful question raised by Nikole Hannah-Jones’s recent writing about her daughter’s educational experience. Parents make enormous decisions on behalf…
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Sometimes an award is really a reminder of who helped you become.
This weekend, I had the honor of returning to my alma mater, Concordia University St. Paul, and receiving the Alumni Association Educator of the Year Award. I didn’t campaign for this one. I was nominated and selected. And that made the moment especially meaningful. Standing there, I thought…
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IRS Changes, School Boards, and the Urgent Need to Plan
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...
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Back-to-School Nights: Building Community, Not Conflict
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...
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Let Them Roam: Rebuilding Childhood Resilience
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,...
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IRS Proposal Threatens School Diversity Programs — What Leaders Need to Know
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...
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First Full Day K–12: Back on Campus and Ready
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.…
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What if the key to student retention starts with the faculty?
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…
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The first week of school isn’t just a reset for students. It’s a reset for you, too.
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...
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Your school’s policies don’t interpret themselves.
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...
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Hot Start: Faith, Faculty, and the First Week Back
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...
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Belonging Before the Bell: Leading with Purpose
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?…
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When AI makes the work faster, are we still doing the thinking?
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...
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Leading Through the Storm: School Governance in Contentious Times
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...
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Healthy Boards, Healthy Schools: Back-to-School Governance Tips
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....
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Pause, Jot, Lead: How to Stay Present When Work Gets Personal
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...
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Be a Tourist Again: Rediscovering Joy in Education
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…
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August Launch: Preparing Your School-Year Rhythm
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...
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Make Equity Built In: Governance Over Add-On DEI Work
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...
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You Made It: Closing Week Salute for Educators
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…
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Memorial Day Musings: Community, Sacrifice, and School Planning
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…
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Five Signs a Leader Needs Executive Coaching — A School Leader's Guide
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...
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9 a.m.–7 p.m.: Your Ideas Belong to the Job — After 7 They're Yours
Dr. Chris Dennis shares a morning anecdote about reconnecting with a former student and a mentor's advice: "Between 9 a.m. and 7 p.m., your ideas belong to your employer—after 7 p.m., they're yours." The episode encourages educators to protect their private time, pursue personal goals, and be...
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The Loneliness of Leadership: Finding Support in Your Professional Community
Dr. Chris Dennis reflects on end-of-year school traditions and the bittersweet milestones of graduation, then explores the dual nature of leadership—public applause and private loneliness. He urges educators to lean on professional networks, affinity groups, and associations for support, and...
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Trust Your Systems: A Midday Boost for Educators
Host Dr. Chris Dennis drops a short, uplifting message from inside the school day, encouraging educators to trust the systems they’ve put in place and to find moments of joy amid end-of-year stress. With a live backdrop of students rehearsing and practical reminders to have hard conversations and...
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Prep Now, Thrive Later: Planning Your Best School Year
Dr. Chris Dennis reflects on recovering from an accreditation visit and offers concise leadership advice for closing the school year and preparing for the next one. He discusses scheduling, staffing, summer prep, and keeping work aligned with your school's mission. He urges leaders to check in…
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Don't Take the Bait — Finish 2026 Strong
Dr. Chris Dennis encourages educators to stay focused as the school year reaches its midpoint: resist distractions, avoid negative narratives, and remember the intentions you set in December. Take time to rest, review your plans, course-correct if needed, and re-engage with renewed energy—there's...
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Demystifying School Boards: What Educators Need to Know
Hello, and welcome to another episode of On the Way to School. In this episode, Dr. Chris Dennis demystifies school board governance — explaining the board’s fiduciary role, strategic responsibilities, and how educators can engage with or even serve on boards — while emphasizing discretion and…
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When Your Career Needs Its Own Accreditation: Self-Study for Educators
Dr. Chris Dennis discusses the importance of treating your professional growth like a school accreditation: perform a self-study, measure your leadership against your organizations mission, and seek feedback to improve. He also encourages educators to volunteer for accreditation visiting teams as…
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Deposit Day Decisions: Celebrating College Commitments and Milestones
Good morning, and welcome to another episode of On the Way to School. Host Dr. Chris Dennis celebrates College Tuition Deposit Day, shares excitement about visiting his alma mater after 25 years to speak with students, and reflects on personal stories, from being a teenage parent to playing…
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Recognition That Sticks: Small Gestures, Big Impact for Teachers
Episode 200! Dr. Dennis celebrates a personal family milestone, reflects on end-of-year school rhythms, and then focuses on the importance of authentic recognition and rewards for faculty. Using survey findings and classroom visit anecdotes, he emphasizes low-cost, meaningful practices—sincere...
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Money Moves: How to Ask for A Raise
On The Way To School host Dr. Chris Dennis breaks down how to approach raises and promotions, especially for educators navigating step scales and limited negotiation windows. Learn what percentage counts as a good raise, how to identify the exact number you want, use industry comparables, and…
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Crisis as Curriculum: Leadership Lessons from the Storm
Dr. Chris Dennis explores how crises, from the COVID-19 pandemic to power outages and wildfires, serve as an informal curriculum for school leaders, revealing lessons in decision-making, responsibility, and community care. He shares personal experiences, the costs of crisis leadership, and...
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Dear Graduate: When the Applause Stops, Navigating the Quiet After Graduation
Host Dr. Chris Dennis reflects on the silence that follows graduation and offers practical encouragement for graduates and parents. He reframes post-commencement uncertainty as transition, not failure, and suggests breathing room, self-reflection, and community support. References include his…
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We're Trying: A Leader's Check-In
Dr. Chris Dennis offers a short check-in for educators and administrators, acknowledging the unseen work leaders do, the complexity behind decisions, and the importance of recognizing effort across teams. He encourages listeners to finish April strong, celebrate small wins, and take care of...
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Racial Identity in the Boardroom: Governance That Sees Everyone
Dr. Chris Dennis explores how racial identity and other invisible identifiers shape decision-making in K–12 independent school boardrooms and why boards cannot simply set identity aside when governing. He introduces the idea of culturally affirming board governance, outlines how identity affects...
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Leadership Is Now: Own Your Role Today
Welcome to On The Way To School with Dr. Chris Dennis — a quick episode for educators to reflect on career and leadership. Dr. Dennis argues that leadership is not a future promise but a responsibility in the present, urging listeners to evaluate how they communicate, document, and take...
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Dear Graduate — Crossing the Finish Line
In this episode of On The Way To School, Dr. Chris Dennis launches the new "Dear Graduate" segment and focuses on the idea of the finish line as a real but recurring transition. He encourages graduates to view completion as a handoff to the next version of themselves, to be intentional, ask...
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Accountability at Closing Time: Leading with Transparency in Schools
As the school year ends, leaders face heightened accountability—contracts, budgets, enrollment, and outcomes drive tough conversations across independent schools. Use data and clear policy, anticipate questions, and explain context rather than react defensively. Dissect power dynamics, avoid...
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May 1st Decisions: Helping Students Bounce Back from College Rejection
Dr. Chris Dennis discusses the May 1 college deposit deadline and the emotional journey students and families face when admissions results don’t match expectations. He explains reach, target, and safety school strategies, shares personal stories about supporting seniors through disappointment…
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The 'Bad Word' in Education: Confronting Grade Inflation
Dr. Chris Dennis examines grade inflation since the pandemic, its effects on college admissions and student equity, and why authentic grading matters. He explores challenges teachers face, the role of clear rubrics and family communication, and urges K–12 and higher-ed collaboration to restore...
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Beyond the Score: Measuring Growth, Not Just Achievement
In this episode Dr. Chris Dennis explores the difference between achievement and growth, and how traditional standardized tests can miss the varied forms of student capital. He discusses community cultural wealth, the limits of single-point assessments, and practical strategies—like interim…
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Content, Not Complacent: Embracing Where You Are
Dr. Chris Dennis explores the value of being content in your role and resists the pressure to constantly chase change. He offers three practical reminders: applaud your accomplishments, give yourself grace, and cultivate identity beyond work. This short episode encourages educators and...
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Clarity, Capacity, and Power: Collaboration Tips for Educators
Dr. Chris Dennis explores three practical elements of effective collaboration in schools: clear roles and responsibilities, knowing your capacity and when to step in, and navigating power dynamics that affect teamwork. These brief, actionable tips are designed to help educators and leaders…
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When You're Not Chosen: Turning Rejection into Growth
Dr. Chris Dennis discusses how to respond when you’re passed over for an opportunity—encouraging self-reflection, identifying fixable truths from the process, and seeking coaching to recover. He offers personal examples and practical steps for educators and administrators to regain perspective,...
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Aim High: Landing Your Next Big Role in Education
Dr. Chris Dennis breaks down three practical strategies for educators entering the job market: work with a coach to prepare, aim higher than the obvious next step, and use warm introductions to build trusted connections. He also offers to connect listeners with coaching referrals and gives quick...
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Re-entry Ready: Prep, Process, Play for a Smooth Return
Dr. Chris Dennis shares a quick, practical guide to returning after spring break with three simple steps: prepare your week, process what the break meant to you, and make room for play. He discusses how to recalibrate your focus as a leader, offers upcoming episode topics like job hunting, and...
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Lonely Graduation Launch: From Leimert Park to Minneapolis — A Bestseller Story
Dr. Chris Dennis recalls the whirlwind launch week for his new book, Lonely Graduation, from a packed Leimert Park bookstore event to campus talks at Hamline University and a bestseller debut on Amazon. He shares highlights from launch events in Los Angeles and Minneapolis and reflects on the...
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Spring Break, Book Launch, and the Hustle of Doing It Yourself
Dr. Chris Dennis returns with a short update: apologizing for a missed episode, celebrating spring break, and encouraging educators to rest and recharge. He announces the launch of his book Lonely Graduation (March 24) and related events in Los Angeles (Mar 25), Hamline University (Mar 26), and...
About this show
🎙️ On the Way to School: Six Minutes to Elevate Your Educator’s Day 🎙️ Embark on a transformative journey with On the Way to School, the essential podcast for educators and school administrators seeking to enrich their mornings with impactful insights. Each concise six-minute episode delivers powerful tips and strategies to empower your educational leadership and classroom effectiveness. What You’ll Discover: - Conflict Resolution: Master techniques to navigate and resolve classroom and administrative disputes smoothly. - Leadership Skills: Develop and refine your leadership qualities to inspire and guide your team and students. - Social Justice in Education: Explore actionable strategies to foster an inclusive and equitable learning environment. - Growth Mindset: Cultivate a resilient and positive mindset that encourages both personal and professional development. - Daily Motivation: Receive daily doses of inspiration to keep you energized and focused throughout the school day. Why Li
Hosted by
Christopher S. Dennis
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