Leadership interview with Heather Thomas, Greenwood College School

There’s this positive energy at Greenwood, which is really lovely. When people ask me what I love about Greenwood, I go straight to the people. It’s the students, it’s the staff, it’s the families. I often hear that Greenwood students enjoy being at school, and not only that, the staff enjoy being here too. I think that’s just wonderful. I love being part of this community where people really care about each other, and you can feel it.

I have had the privilege of being at Greenwood for over 20 years now. I started my professional journey at another independent school in the Toronto area and then joined Greenwood as a teacher of physics, math, and science. The following year, I became the department head of mathematics and business. A few years after that, I became the director of student learning, then director of personalized learning, then vice principal of student learning, deputy head of school, and now head of school and principal. It has been a journey that has really fed my passion for academics, experiential learning, student growth, and student engagement.

I’ve always been interested in experiential learning, something that grew out of my time as a camp counsellor, canoe trip guide, and assistant camp director. I was able to bring that into the classroom and connect it with student engagement. I was one of the first people at Greenwood to develop blended learning courses more than 15 years ago, creating technology-rich courses that students could self-direct. Since then, we’ve integrated technology into everything we do. That passion for experiential learning, technology, and student-centred approaches has strongly influenced me.

What resonates most with me is the notion of personalized learning that we really lean into at Greenwood. The idea is that every student is capable of growth, and every staff member is too. We focus on people as individuals and genuinely care about each member of our community. This sense of care filters into classrooms, where teachers build supportive environments where students can take risks, try things, and help each other move forward. Teachers give students individual attention, stretching them when needed and supporting them when they struggle. This same emphasis extends to teacher development, ensuring they have the skills to meet student needs.

Greenwood has a unique culture built upon a true sense of community. You can feel it when you walk in the building—there’s a welcoming atmosphere we work hard to nurture. I personally think the community at Greenwood is second to none. Providing high-calibre academics while supporting student well-being is something Greenwood does exceptionally well. Teachers and advisers play a huge role in this, listening to students, considering their whole lives, and responding to their needs. Our adviser program is particularly strong. It is run as a timetabled course, and advisers choose to participate because they want to mentor students. Advisers guide students in academic growth, social-emotional development, and life skills, becoming their number one advocate in the school.

We are incredibly nimble, innovative, and reflective, always asking how we can improve. Right now, we’re in the middle of developing a new field and green space, which will be transformational for the school. Having our own outdoor space will allow athletics practices, classes, and health and physical education programs to thrive without relying on off-site facilities. It will also provide a space for students to gather, eat lunch, and study outdoors. This change has been years in the making and represents the kind of growth and innovation we embrace.

The families at Greenwood are truly part of the community. They are great people who genuinely want to partner with us. Families support school initiatives, from decorating for Halloween to judging business case competitions, and they partner with us to support their children. When we see a student who needs more support or stretch, we start by working with parents and advisers. That partnership is huge in helping each student continue to grow.

When conflicts arise, listening is key. We have several staff members trained in professional coaching, which gives them skills in listening, questioning, and learning. Understanding what’s important to people allows us to find common ground. Conflict can be a growth opportunity, teaching people about themselves and about others. While no one enjoys conflict, it can lead to important learning and development.

I encourage parents and prospective students to look at different schools and align what a school offers with the needs of the individual student. Every independent school in Toronto is excellent, but each has its own character. At Greenwood, you will find high-calibre academics, an outstanding adviser program, and a culture of care and innovation. Our alumni are confident self-advocates who contribute to their communities. Greenwood is a place for all students, but the ones who thrive here are those who want to be involved, embrace challenges, and value community. Our twice-yearly outdoor education trips highlight this, as students develop friendships and build skills such as resilience, collaboration, and problem-solving. Students who want to grow in community do especially well at Greenwood.