The Sterling Hall School School Leadership
The Sterling Hall School’s leadership emphasizes belonging, strong relationships, and a boy-centred approach tailored to students’ developmental needs. Leadership says it prioritizes character, whole-child growth, and close partnership with families, while maintaining a small-school environment where boys are known, heard, and encouraged to take risks.
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Insider community voices
Hear directly from The Sterling Hall School community as they share insights into the School Leadership.
Facts and analysis
MESSAGE FROM THE LEADERSHIP
We invited Rick Parsons, Principal at The Sterling Hall School, to share a message.
The overview highlights the vision, values, and guiding principles that shape leadership and the student experience at The Sterling Hall School.
Rick Parsons, Principal
Dear Families:
I have been asked with some regularity to describe the “typical” Sterling Hall boy. My answer always remains the same: there is no such thing as a “typical” Sterling Hall boy.Boys belong here, whatever their interests, whatever their aptitudes, whatever their learning requirements might be. We have a created an environment where boys have a sense of acceptance and belonging that gives them the confidence and security they need to take risks, try new things, be themselves and reach for their potential in all their endeavours.
Our approach is unique among schools in Toronto. We focus entirely on boys during their formative years from Junior Kindergarten to Grade 8 – a period when a boy’s life is filled with energy, curiosity and exploration.
We inspire our students by using the most successful techniques and approaches for teaching boys. We treat every one of them as individuals, exposing each of them to a curriculum that is specifically catered to boys’ learning during the key foundational years.
Our exceptional teachers are actively involved throughout the journey, providing support and encouragement. Parents are part of a warm and open school community that is made up of current and Alumni families, Old Boys, faculty/staff, friends, donors, volunteers and members of our Board.
We welcome you to visit The Sterling Hall School and thank you for your interest. We encourage you to get to know us and to see what makes us so proud of our program and our boys. I believe that you will see a school that knows what makes boys tick and what they need to become caring, confident and empathetic young men who are capable of, and interested in, making a difference in their world.
Sincerely,
Rick Parsons
Principal
The Sterling Hall School
INTERVIEW WITH THE LEADERSHIP
We interviewed Rick Parsons, Principal at The Sterling Hall School.
In conversation with school leadership, the discussion centred on the school’s mission, educational approach, and the vision shaping key decisions.
Rick Parsons, Principal of The Sterling Hall School, discussed the school's distinctive approach to boys' education, emphasizing character development, strong teacher-student relationships, and a deep sense of belonging. He highlighted Sterling Hall's focus on meeting boys where they are developmentally, partnering closely with families, and preparing each student for a high school that best matches their evolving interests, strengths, and goals.
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- 0:59 - Please describe your professional journey leading up to your current role at The Sterling Hall
- 3:03 - What have been some of the major influences on you and how you approach your work?
- 5:41 - What strategies does the school rely on to equip students to thrive both academically and personally?
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Highlights from the interview
In my time at Sterling Hall, I've embraced a few other roles. In 2017, I began co-facilitating the orientation for all new heads of K–12 schools. I've been doing that ever since. In 2018, I joined the International Boys' Schools Coalition as a trustee, one of two Canadians on that board. I did that for seven years and retired from that role in 2025.
I've had innumerable mentors as a young person growing up. I continue to have mentors now in the form of coaches, teachers, administrators who work with young people, and, of course, so many students that we learn from. They inspire me and engage me every day.
I think that relational connection is seminal to reaching young people. We know that emotions are the light switch to learning, and building those connections with them, I think is essential.
- We say this at Sterling Hall: we either succeed or we learn.
We say this at Sterling Hall: we either succeed or we learn.
Academics are a significant part of learning and growing up, but they're within the fabric of something even more important, which is developing beautiful humans. Humans who are resilient and have the capacity to overcome challenges, grow from them, and learn from them.
At the end of the day, it's the whole child that we're concerned about, and it's the whole child that we're developing.
We're teaching the boys; we're not teaching the subject. If the boys need to stop and have a circle, and these happen quite regularly at our school, we're going to address it… We're going to get out on the table what's happened, resolve it, co-create a solution with the boys, give them agency, and let them be heard when something is upsetting them. Then we're going to move forward.
We're going to expand our campus, but we're not really expanding our enrollment. We're maintaining the small school that we have because we think there's a small-school advantage to the relational connections, the sense of belonging that we foster, and the confidence and opportunities the boys can gain from that environment.
I think the new development we have on the horizon is going to be a game-changer for us as a school. It's a beautiful two-storey building, parking on campus, and a new northwestern green space that the boys are going to love and that we're going to connect to our programming in a wonderful way.
Partnership with families is perhaps one of the most important things in our school. I think we have a very active and engaged community, which is incredible and positive.
We are very unapologetically boy-centric, so the assemblies are amazing. They may not be the most polished thing you'll ever see, but they're giving boys an opportunity to lead.
When we promote a sense of belonging, we give boys the confidence and opportunity to take risks. It's that risk-taking that leads to growth. Those risks might be social when they first come to the school, but they could also be artistic, athletic, or creative; it doesn't matter.
When the same values and expectations about how we behave are reinforced both at school and at home, they resonate more with the boys and help them understand how to correct their behaviour in a positive way.
I really believe in separating the boy from the behaviour. I think that separation is very important because it prevents shame, and shame is a negative emotion that doesn't help anybody.
I would say Sterling Hall's greatest strength is also its greatest weakness, which is that we go from JK to Grade 8. A lot of people get worried because they think it's so important to get into a particular school and graduate from a particular school.
I would argue that our niche in the city of Toronto is that we're not focused on high school or post-secondary education. All of our thinking, our professional development, our resources, everything, is focused on these elementary years.
The families who come to us recognize that their boys are going to change. Our role is to meet them where they are at every stage of their development and help them find the next best place for high school.
One of the great strengths of our school is that we have a common language around character. Character is reflected on the first page of every report card, where every student from Junior Kindergarten through Grade 8 completes a self-reflection on their character strengths.
