The LearnIt Podcast with Dhiraj Hariramani

Jennifer Reid,Trinity College School | Middle school is the most rewarding age

In this episode of The LearnIt Podcast with Dhiraj Hariramani, we sit down with Jennifer Reid, Head of Junior School at Trinity College School in Port Hope, Ontario. Jennifer started as a Phys Ed teacher in the Junior School, moved into student academic support, and now leads the school her younger self walked into. This conversation traces what that arc has taught her about middle schoolers, parents, and what makes a school feel like a place a kid actually wants to walk into. In this conversation, Jennifer shares: * The teacher who set her path: a high school Phys Ed teacher who doubled as guidance counselor and made everything feel accessible. * What changed when she took the Head role: suddenly being privy to budgets, staffing, and parental concerns that had been invisible to her as a teacher. * Why middle school is the age she finds most rewarding: a mix of curiosity and awkwardness, kids who pretend they don't want guidance but still crave it. * The Third Path's "five deposits to one withdrawal" model and how she uses it to build relationships before hard conversations. * Her standing morning practice: being outside as the bus drops off, in the hallways during the "collision hours," walking into classrooms not to evaluate but to join in. * The Power of Moments framework on elevation, insight, pride, and connection, and how she peppers ordinary days with something extraordinary. * Why she still believes it's never too late to learn a skill, and what humming, marathons, and a three-wheel motorcycle have to do with school leadership. #TheLearnItPodcast #LearnIt #OntarioEducation #TrinityCollegeSchool #JuniorSchool #MiddleSchool #IndependentSchools #CAIS #EducationalLeadership #HeadOfSchool #SchoolCulture #StudentWellbeing #CharacterEducation #ExperientialLearning #PortHope

Deirdre Timusk: Inside Havergal College with Head of Senior School

THE LEARNIT PODCAST WITH DHIRAJ HARIRAMANI FEATURING DEIRDRE TIMUSK In this episode of The LearnIt Podcast with Dhiraj Hariramani, we sit down with Deirdre Timusk, Head of Senior School at Havergal College. After 19 years at Upper Canada College, including roles as math department chair, senior house adviser, and assistant head, Deirdre crossed Toronto to lead at one of Canada's most established independent girls' schools. Next year she steps into a new role in Admissions and International Recruitment as Havergal expands its boarding program. IN THIS CONVERSATION, DEIRDRE SHARES: * Growing up as the fourth generation of teachers in her family, shaped by the scholarship that changed her father’s life. * The greatest culture shock of her career while teaching in St. Louis. * The unplanned speech that changed how she saw her role as a leader. * What is different and what is the same between boys' and girls' schools. * Why she co-founded the CIS Ontario Women's Network. * Her case for single-gender education for girls. * A lesson from auditioning for the National Ballet School at age 9. * What she would do if money were no object: needs-blind admissions. This episode is for every independent school leader, every educator thinking about the next chapter of their career, and every parent weighing the question of coed versus single-gender education. #TheLearnItPodcast #LearnIt #OntarioEducation #HavergalCollege #UpperCanadaCollege #IndependentSchools #GirlsEducation #EducationalLeadership #WomenInLeadership #CISOntario #SchoolLeadership #BoardingSchools #Admissions #StudentWellbeing #K12Education

Curtis Ennis, Halton District School Board: Why Teachers Must Be Learners

The LearnIt Podcast with Dhiraj Hariramani In this episode, we sit down with Curtis Ennis, Director of Education and CEO of the Halton District School Board. Born in Jamaica and raised by a mother who never went to school herself, Curtis spent years in banking before walking away from a promotion to become a teacher. Today, as Director, he leads one of Ontario's largest school systems through what he calls adaptive challenges—the problems that have no playbook. In this conversation, Curtis shares: * His mother's quiet conviction: how she sewed together a school uniform so he could keep going to class, and why that memory still drives his work in education. * The volunteer day that changed everything: the moment at a school, while he was still a bank manager, when he felt something he had never felt at the bank. * The hardest year of his life: working full days at York University and bank back-office shifts past midnight, with two young kids at home. * Why he leads people first: how investing in a principal nobody else wanted to work with taught him that people respond to how they are valued. * Confident humility: the leadership idea he has come to embrace, the belief that confidence and humility are not in tension. * The student who taught him to protect his peace: a phrase from a session on mental health that he now uses for himself. #TheLearnItPodcast #LearnIt #OntarioEducation #HaltonDistrictSchoolBoard #HDSB #DirectorOfEducation #EducationalLeadership #SchoolLeadership #K12Education #PublicEducation #LeadershipDevelopment #StudentWellBeing #GrowthMindset #MentalHealthInSchools #AIinEducation

Adam Hurley, HTS Global Online Campus: The Future of Online Education

In this episode of The LearnIt Podcast with Dhiraj Hariramani, we sit down with Adam Hurley, the Inaugural Principal of HTS Global Online Campus, part of the Holy Trinity School network in Richmond Hill. From teaching student athletes at the Canadian International Hockey Academy to founding Blyth Academy's Downsview Park campus, Adam has spent about a decade as a school principal learning how to build schools from scratch. As Inaugural Principal of HTS Global Online Campus, he helped launch HTS's first global online campus, which now serves students from over six different continents. In this conversation, Adam shares: * Starting from scratch with no playbook: How he spent his first six months at HTS as a fly on the wall, soaking in the culture before translating any of it into an online environment. * Hallway conversations, reimagined: Why being able to walk down a virtual hallway and talk to a student in the Congo, a student in France, and a student down the street is what makes HTS Global a full school experience rather than just a collection of courses. * What online teaching actually requires: Why a skilled in-person teacher is not automatically a skilled online teacher, and the digital skill set the role demands. * Who online school is actually for: High-level athletes, international students, families who travel often, students dealing with post-COVID social anxiety, and kids recovering from bullying who finally have a safer space to learn. * AI as enhancement, not replacement: Why students jumped into AI as a replacement rather than an enhancement, and what it takes to teach them to use it ethically and thoughtfully. * Flexibility with accountability: The belief he has changed his mind on over the past five to ten years, and why students thrive when they're trusted to take ownership of their own learning. * The teacher he still visits every year: The high school teacher who left a lasting impact on Adam's life, not through curriculum but through relationships, and the legacy Adam wants to leave in education. This episode is for every school leader thinking about building beyond their walls, every parent wondering what online school actually looks like, and every educator holding onto the belief that relationships are still the foundation of everything. #HolyTrinitySchool #HTSGlobalOnlineCampus #OnlineLearning #IndependentSchools #OntarioEducation #GlobalEducation #EducationalLeadership #HybridLearning #AIinEducation #StudentSuccess #TheLearnItPodcast #LearnIt #PrivateEducation #InnovationInEducation #SchoolLeadership

Kim Williams, Superintendent of Learning, TLDSB | Don't Underestimate Our Kids

In this episode of the LearnIt Podcast, we sit down with Kim Williams, Superintendent of Learning at Trillium Lakelands District School Board. From teaching water babies to swim in small-town Ontario to overseeing curriculum and technology for an entire school board, Kim's journey is proof that sometimes, the people who never wanted to leave the classroom end up making the biggest impact far beyond it. In this conversation, she shares: * "We Don't Call It Cheating When Adults Do It": When parents help with homework, we call it engagement. When a student whose parents work night shifts turns to AI for help understanding a math question, we call it cheating. Kim challenges that double standard and reframes AI as an equity tool, not a shortcut. * School Wasn't His Thing: Kim's brother dropped out of grade 12 — with an IQ far above hers. School simply didn't serve him. That experience, combined with growing up with an invisible speech impediment, became the driving force behind her career: fighting for the students who don't fit the traditional box. * They're Only Thirteen: In Ontario, students choose their academic pathway in January of grade 8. They're 13 years old, and that decision directly impacts their future earning potential. Kim makes the case for destreaming — giving students one more year to breathe before we ask them to decide their future. * Teachers Can't Just Teach the Curriculum: We're asking teachers to be parents, mental health counselors, and conflict mediators — all before the first lesson starts. Kim's advice? You don't have to solve every problem. Just be kind. Students need to know you care before they can access any learning. * A Young Man in Shoppers Drug Mart: Kim ran into a former student in the middle of a store aisle — a kid who fought his parents to pursue construction instead of university. He was beaming, telling her about his rapid rise into management. Her takeaway: don't underestimate what kids can do when you light a fire inside them. Just get out of their way.