Co-Piloting the Future: How Myke Healy is Preparing Students and Teachers for an AI-Augmented World
From international exchanges to AI-integrity research, Trinity College School’s Assistant Head - Teaching & Learning reflects on his journey and looks ahead to leading St. John’s-Ravenscourt School starting July 2026.
If you had told Myke Healy 23 years ago that he’d one day become Head of School at one of Canada’s top independent schools, he might have laughed. Back then, he was building a timber frame home in a rural Ontario, raising a newborn, and working in overseas experiential youth programs.
“I didn’t apply to work at Trinity College School because I had some master plan,” Myke said on The LearnIt Podcast. “I needed a job, saw an ad in the Globe and Mail, and said, why not? That was over 20 years ago. I never left.”
Since then, Myke has built a reputation as one of the country’s most thoughtful and future-focused educators, someone who champions academic integrity, teacher growth, student wellbeing, and the thoughtful use of technologies like generative AI.
Now, after more than two decades at Trinity College School, Myke is preparing to take on a new challenge. In July 2026, he will begin his next chapter as Head of School at St. John’s-Ravenscourt School in Winnipeg. His move marks the beginning of a new era for the Manitoba-based institution and underscores his commitment to shaping national conversations about leadership, innovation, and the future of learning.
Global Roots, Local Leadership
Myke’s early career wasn’t spent in a classroom, it was spent in the field. With Canada World Youth, he designed and led experiential learning programs across Thailand, India, Mongolia, and Sri Lanka. “It was the best job,” he said. “Travelling, working with youth, watching them grow through service and culture shock, it shaped everything I believe about education.”
That philosophy followed him to Trinity College School (TCS), where he currently oversees curriculum, teacher development, online learning, and pedagogical innovation. It’s a role he describes as “part coach, part connector, and part learner.”
Supporting Teachers Across Their Journey
Myke firmly believes that the best schools invest in their teachers, at every stage of their career. He’s structured TCS’s professional development around what he calls “age and stage support.”
“New teachers need structure, mentorship, and AQ courses. Mid-career teachers need inspiration and opportunities to deepen their craft. And later-career teachers should be mentoring the next generation,” he explained.
the School currently supports multiple teachers in completing their master’s degrees. “When teachers are engaged in their own learning, students benefit. Full stop,” he said.
This mirrors research from John Hattie, whose findings on teacher efficacy and ongoing development show it has one of the highest impacts on student achievement.
A Culture Where It's Cool to Be Smart
TCS is known for its academic excellence, and Myke is proud of that. “There’s a culture here where it’s cool to be smart,” he said. the School supports a rigorous AP program, with teachers required to complete additional summer training to offer enriched coursework.
But rigor isn’t about stress, it’s about support. “We tell students: we submit our work on time, and we do it with integrity. That’s the kind of school we are,” Myke said.
On Friday nights, students missing assignments are invited, gently but firmly, to the library for a supervised work session. It’s part of the culture of accountability and care that defines TCS.
Myke Healy on The LearnIt Podcast
Addressing the Tech Tug-of-War
Like many educators, Myke is grappling with the impact of devices and social media in schools. An analysis of two weeks of incoming data to the boarding school found that 55% of internet traffic at TCS was from TikTok.
“That was a wake-up call,” he said in terms of the impact of the TikTok algorithm on young people. The school has an ‘out of sight, out of sound’ policy for phone use during the academic day. The goal? More eye contact, more conversation, more presence.
At the same time, Myke isn’t anti-tech. In fact, he’s a doctoral researcher investigating the intersection of generative AI and academic integrity. He coined the term “AI arbitrage” to describe the current moment, a gap between widespread student use of generative AI tools and the education system’s ability to adapt.
“We’re in a liminal space. Students are using AI. Teachers are unsure. Systems haven’t caught up. We need to rethink assessment, writing, even what plagiarism means,” he said.
He draws on the work of scholars like Sarah Elaine Eaton at the University of Calgary, who challenge traditional views of originality in an age of human-AI collaboration. Myke says: “I use these tools myself. It’s how I write, how I think. We need to teach students to use them ethically and thoughtfully, not pretend they don’t exist.”
Bridging High School and University
As both a high school leader and an AQ instructor at Queen’s University, Myke sees a clear disconnect between secondary and post-secondary education.
“Teachers think they’re preparing students for the university they attended 20 years ago. Meanwhile, professors are frustrated students arrive unprepared. Both sides are right, but they’re not talking to each other.”
He believes we need more educators with a foot in both worlds to align expectations and close the gap. “High schools and universities operate like two totally separate ecosystems. We need better collaboration, more shared understanding.”
A Leader Who Stays Grounded
Despite his many roles and titles, Myke remains grounded. He starts each day with a strong coffee, keeps up a regular workout routine, and prioritizes kindness in all his interactions.
“In a professional context, people might not know I’m actually really soft-hearted,” he said. “But I think students need teachers who listen, who care, who build human connection in the classroom. That’s the most important thing.”
As he prepares to become Head of School at St. John’s-Ravenscourt in July 2026, Myke remains focused on the same values that have defined his time at TCS: curiosity, compassion, and a commitment to building schools that not only prepare students for the future but also help shape it.