On The Way To School

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 aff...

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...

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 accountable to their own timelines instead of letting work hours consume creative energy.

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 encourages listeners to update memberships, volunteer, or lead so they can both receive and give guidance d...

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 prepare, this episode offers a calm, reassuring boost to finish the day strong.

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 with staff, value differing perspectives that may challenge the status quo, and pay attention to small si...

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 still plenty of 2026 left to finish strong.

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 the importance of healthy board-school relationships. He also celebrates Teacher Appreciation Week, honor...

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 a hands-on way to learn about their institutions and advance their careers.

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 college football, to inspire young people. He also marks the podcast's 200th episode and thanks listeners fo...

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 thank-yous, supervisor acknowledgment, and intentional presence—and urges schools to include recognition...

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 weigh whether a job change is worth the disruption.

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 practical advice on building support systems and self-care strategies to sustain resilience in educational ro...

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 book Lonely Graduation and journal prompts to help graduates process next steps and steady their transitio...

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 themselves as they head into May.

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 participation and policy, and offers practical considerations for training and equity-focused oversight...

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 accountability in their current roles. He offers practical reflections on temperament, communication, and holdin...

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 questions, and use available resources without striving for perfection. He also reflects on life after advan...

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 stonewalling, and be willing to find answers to build trust and keep staff engaged.

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, and encourages embracing the opportunities at the schools that say yes while building resilience and pers...

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 credibility and fairness in grading.

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 testing and mixed methods—to capture longitudinal progress. Dr. Dennis also emphasizes creating culturally a...

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 administrators to recognize their impact, celebrate milestones, and find fulfillment both inside and outside the...

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 improve partnership, protect professional boundaries, and keep focus on student outcomes.