On the first Tuesday of every month, we’ll announce a new Fearless Female, including a video interview of them sharing their business story. Want to be featured as a Fearless Female?
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The Fearless Female we’re featuring for the month of April is Cherylynne McKee, Principal and Educational Leader of St. Jude’s Scholars’ Hall Private School (SJSH).
Cherylynne McKee has dedicated her life to advancing inclusive, student-centered education while leading the evolution of a multi-generational family business.
Currently completing her Doctorate in Educational Leadership at Western University (graduating October 2026), Cherylynne’s research focuses on building educator capacity to implement inclusive education practices. She also holds a Master of Education in Educational Leadership (Western University, 2023), a Bachelor of Education from Nipissing University (2003), and an Honours Bachelor of Political Science with a Minor in Music from Wilfrid Laurier University (2001).
SJSH is more than a career for Cherylynne—it is her home, her family, and her lifelong passion. Founded by her parents in 1982, she quite literally grew up within the school community. From watering plants and collecting garbage at five years old to tutoring students as a teenager, her path into leadership was both organic and deeply rooted in purpose.
Over the past 14 years, Cherylynne has taken over the daily administration of SJSH, leading a full-time staff of 45 while guiding the school through a period of significant growth and transformation. She was the architect behind the school’s rapid transition to a fully online learning environment during COVID-19—an entire school reimagined over a single weekend.
Her leadership extends beyond programming into strategic growth and operations. Cherylynne has overseen the construction of a 10-classroom and dojo addition, is currently managing the development of another expansion, and continues to guide the school as a thriving, multi-million-dollar organization. At the same time, she has taken on the financial leadership of the business, ensuring its sustainability while honouring its founding mission.
As she prepares to complete her doctorate, Cherylynne is bringing research-driven, forward-thinking leadership to rejuvenate and strengthen a more than 45-year legacy institution. Her work is grounded in a deep commitment to inclusive education, community, and innovation.
Beyond her professional accomplishments, Cherylynne is a devoted mother to two wonderful children—balancing the demands of leadership with the values of family that have always defined both her life and the school she leads.For Cherylynne, SJSH remains what it has always been: her home, her family, and her heart. And through her fearless leadership, she is ensuring its future is as strong and impactful as its past.
To learn more about Cherylynne’s journey as a Fearless Female, watch the interview below (or read the written format).
Tell us more about the school
So, we are a private school. We’ve been in the region since 1982 when my parents actually started the business. It was intended to be a temporary alternative to the publicly funded system where students that were struggling with learning disabilities would come for an intensive programming so they could go back into the public system. It has evolved into being a permanent alternative to the publicly funded system where students that are both neurotypical and neurodiverse are getting intensive instruction and assisting them in becoming successful adults.
Can you tell us more about your team?
I have multiple administrators that work with me. I have a high school vice principal. I have an elementary vice principal, and I have a head of my special education programming.
So, when I move into the role of director of education, they would be resuming the role of the separate principals.
What was your career path?
It’s a little bit of a roundabout way. I didn’t intend to become a teacher. I didn’t intend to get an education. My first degree at Wilfrid Laurier is in political science. I had intended to go to law school. I really wanted to get into constitutional law. I’m driven by the government. I find politics just so fascinating and that’s where I believe my pathway was.
While the universe had other plans, I didn’t get into my law school program of choice. I took a year away from it to essentially decide what I wanted to do. Do I still want to pursue law and politics or not? It was within that year that my father said to me, being that you don’t have anything right now, why don’t you come into the school and just do some work with the kids and do some teaching with them.
It was within the first three months I was like; I fell in love. This is what I was meant to do. I fully decided to put the law school path, close that door and then I went to teacher’s college the following year. It really was a roundabout way of how I came to this. I never would have thought that I’d be leading this business right now. It was not a plan of mine.
Tell us more about your educational background
I went to Wilfrid Laurier for my first degree of a Bachelor of Political Science. I also did a minor in music because I just really loved it. That’s why I chose Laurier at first because they have such a strong music program. I ended up then going to Nipissing University up in North Bay for the Bachelor of Education Programming. Then I taught. I spent the next 15-16 years teaching in the classroom. I taught kindergarten music. I taught OAC philosophy back when there was OAC courses. Most of my teaching career was spent doing social studies at the high school level.
Then it was 2018, I was already in roles of administration. I was bordering both being a teacher and being an administrator. I decided I really want to continue my education, especially if I’m going to really go into this role of administrator. I found this program at Western University in Educational Leadership. I took their master’s program, and I graduated that in 2023. As I was navigating through the Master of Education Programming, I just loved the professional learning I was gathering from it. I didn’t want to stop. I started the doctorate program in 2023 at Western. I will graduate this October with my doctorate.
What are some of the highlights of your career so far?
Early on in my career, I was chosen to attend the learning conference through Nipissing University. I was still quite a young teacher. I went to London University over in the UK. I had written a paper about my pre-service teaching and the role I use of technology and connecting it with the students. That was, I think, my first real taste of being a scholarly practitioner. When I became a teacher, I really sunk into the building of the relationships with the students.
As I started to come out of the full-time teaching, I really wanted to dive back into that scholarly aspect of being a teacher. That’s when my life took me back to school.
What are some of the biggest challenges that you have faced so far?
The single greatest challenge. There’s been a lot along the way, of course. There’s always ups and downs. The single greatest challenge being a principal at this time was COVID. It was totally unprecedented. No one had anticipated it. Everyone was asking me for answers that I did not have. I will never forget when Doug Ford announced that schools had to be closed. We don’t have a March break. Our school has an April break.
On Thursday, March the 12th, when Doug Ford made the sweeping announcement that schools would stay closed after the March break, it hit me like, we don’t even have a March break. We are supposed to open our doors again on Monday and start. I had an emergency meeting with my entire team Friday morning at 7 o’clock.
I told every teacher, scrap whatever you have right now. Throw away every lesson plan you have. Everyone’s getting on Edmodo, which was a platform that no longer exists. Everyone’s getting on Edmodo. You’re building a classroom. Make sure every student has access to the Edmodo account. Write out instructions for parents. Class starts at 8.30 in the morning. I spent the weekend figuring out how I could have class start on Monday.
One of my parents of our graduates that has left now, they graduated. He is a professor at Conestoga College. He let me know, Conestoga is using this program called Zoom. You should look into it. I spent that whole weekend researching and figuring out how Zoom works. I purchased an account for every single teacher. On Monday morning at 8:30, class began with all the students in class, all the teachers on Zoom, class ready to go. Those initial weeks of the closure were the most exhausting and probably some of the most rewarding weeks. It really taught me going into something that difficult.
I always questioned myself as a leader of, am I really legitimate? I was just a teacher at one point. Who am I to say what everybody can do? When everyone turned to me and just followed what I had to say, it really legitimized that, no, I have a voice here and I can do this. It was an incredibly challenging yet very rewarding time period.
Knowing what you know now, would you have chosen a political career or done anything differently?
No, I have been offered. I have been offered by different political parties to put my name in, but I’m not interested. I’m not interested to run for local governments. I’m not interested. It’s too much of a putting your personal life out there and that’s just not for me. What I would have done differently is, when I expanded my leadership team, I really saw the value of having other voices and that I didn’t have to carry the burden of leadership alone.
I think if I were to change anything, I would have expanded my leadership team probably sooner. They’re invaluable to me. I would have gone back in time and said, you don’t have to do it alone. You can expand your leadership team. I would have done that differently.
What methods have you used to grow professionally?
Yeah, I’d say my connections with my colleagues are massive. And so through Western University, that has really helped my leadership grow. So not only learning about the scholarly aspects of it, but I have colleagues now all over the world. I have some colleagues in Vancouver and BC, up in Thunder Bay, Calgary, but then also in Hong Kong, in parts of Europe, because the way that the University of Western does it is through Zoom.
So, it’s all online. I have all these amazing colleagues from all over and connecting with them regularly, hearing what their challenges and their successes are, me sharing mine, I have found that that connection with other leaders has been tremendous in understanding myself, but then also helping myself grow. And then adding in the scholarly aspect of it as well.
The last five years have been spent researching and reading has caused me a lot of reflection on my own leadership and say, well, what type of leadership am I doing? Which leadership does feel more natural to me? And so, all of that self-reflection combined with the connections with my colleagues has been tremendous.
What does your work routine look like?
Yeah, so evenings and weekends are spent at school learning. This final year, I’ve been writing my dissertation. And so I’ve been lucky enough that I’ve been able to take Wednesdays off. So, I don’t come to school on Wednesdays, and my team of leaders take care of everything here at the school. And then I’m able to spend a full day at home just writing and researching where it’s nice and silent.
I do have two young kids. So, evenings and weekends are, I’m a mom, so I must spend that time with them. But my Wednesdays have been instrumental.
How do you define success?
That’s a really good question. My success is defined by the success of others. And so, my form of leadership is very transformational leadership. I’m really connected with others and building others. So transformational leadership is all about making other leaders. And so when I have a student who I’ve been working with, even if it’s something minor, a young child that’s not understanding how to add or subtract or carry or borrow, or they’re just struggling with something, and if I just help them a little bit, and then that glow of I did it, that glow of I’m successful now, that tells me that I’m successful.
Up until university, just the other day, I got an email from the student that I had taught well over 10 years ago. And she’s now at the University of Cambridge in the UK, and she’s getting her PhD in chemical engineering. And she sent me an email out of the blue, Mrs. McKee, my time with you was pivotal in my learning.
And it’s like, you never really know what kind of impact you’re making on somebody. And so, I look back at that, and I go, wow, that to me feels like success that I’ve had this impact on these kids.
Do you think teaching as a profession is undervalued?
I don’t know, that’s a good question because I think everyone views it in a different way. But I can only really say how I view it. And what I tell my teachers is that we’re not really here to teach curriculum. Like that’s just the medium we’ve been given. What we’re here to do is raise children. And so, it there’s so many more things that are involved in that.
You know, there’s soft skills involved in that. There’s advocacy involved in that. There’s self efficacy that’s involved in that. There’s, there’s so much more that’s involved. And I think, I think that gets missed. Some people forget that that’s what teaching is about.
Yes, I want your child to learn how to read and write, I want them know the difference between or I want them to know the causes of World War One. But in the end, it’s more about the relationships we build, it’s more about the person that they become. And so, as a teacher, as a principal, I’m always reminding teachers that stop focusing on the curriculum, it almost sounds counterintuitive but stop focusing on the curriculum and focus on the child.
And I think that gets missed with a lot of people, they just see the job, they see the position and they miss that that’s what we’re here for.
What core values drive you?
So, the core value that really guides everything that I do is an ethics of care. The students that are in my school are people. And again, I think too many adults minimize the worries of a child, and they say that they’re too simple. But when a six- or seven-year-old child is upset because they can’t, they can’t find that favorite eraser of theirs. In that moment, that means everything to that child.
And as adults, if we dismiss the child, it teaches them that the adult doesn’t care. And so whereas if I pause, and I show that child, how you feel matters to me right now, and I take the time to help them find that favourite eraser that they have, it teaches them that they voice their concern to an adult, the adult will validate it, and there’s so many lessons involved in that. And so, yeah, the value that really guides everything that I do here at the school is that ethics of care.
What methods did you use to grow your team and recruiting talent?
Building strong teams is again, all through transformational leadership. So, I am very consciously aware of building relationships with my teachers and my staff. And building a team lies in the space between actions I have found.
And so, it’s not the to-do list. It’s not the meetings we have. It is the interactions that we have. It’s the relationships that we build. It’s all of that builds that trust and that bond between leader, and teacher or leader and employee, so that if I do need to put my foot down as a boss to say I need this to happen, there’s so much trust and relationship built that even if the person doesn’t understand why I’m making that decision, they will accept the decision. So, all of the team building happens in all of those little, small spaces between meetings and between the to-do lists and between those things.
And then attracting new hires. I’m fortunate enough that the school has an incredible reputation. We have an incredibly low teacher turnaround rate. And more teachers are attracted by our, let’s call it traditional model, where we’re very low technology. There’s a lot of administrator support with teachers here that some teachers feel they don’t have in other places. And so, there’s not a lot of advertising or call out that I must do.
I find that some teachers are really drawn towards my programming. And so, then it’s about finding the best of the best that get drawn to me.
What do you look for when hiring a new teacher?
So, when I’m looking to hire somebody, if I have a space available, of course I want to look at the resume. I’d like to see what you’ve done, where you’ve gone to school, the experience that you have. To me it’s not about the degree hanging on the wall though. It is more about the relationship that I see within the person.
I like to hear about experiences of them working with other students, the challenges that they’ve faced. I often ask about, tell me a story when a student or a class really challenged you. What did you do? How did you cope through that? Who did you lean on to get assistance? And I really love to hear those stories that the person is bringing to us.
I also like to bring somebody on who’s got interesting passions. And so, if I had a teacher, and if she’s listening, she’ll know who she is, but I had a teacher who was into bell ringing. And so, she said, I would love to have a bell club here. And so we bought all the bells, and she taught the students how to do bell ringing. And just such an interesting aspect to who she is. So yes, I’m looking for somebody who knows the curriculum, but I’m looking for somebody who’s really intent on building those relationships and then who can bring their own passion into the school.
What are your views on Waterloo Region?
I really love the Waterloo region. I’ve been here my whole life. So, I almost wouldn’t consider working anywhere else. But what I really love about Waterloo is that it is this, it is still a small town. It’s very much a small town. Like I meet someone like yourself, I’m like, where did you go to high school? And where did you, oh, I went to this high school. You went there? Like there’s such a connection of the people who’ve grown up and who have been in this town. And we all know somebody who knows somebody. And there’s this connection that exists within Kitchener-Waterloo, this small-town atmosphere.
But with our growing population, we also have this kind of big city atmosphere. So, we get the best of both worlds of being this large city with all the wonderful things that come with it. And then also that small town feel. And I found that the networking in Kitchener-Waterloo is strong because of that small town feel. That’s amazing. And if we want to talk about that a little more, you mentioned networking.
What are some tools in networking that you’ve seen, or you use yourself in the region that makes it, you know, better for you to meet people?
I guess nothing. Again, I’m much more of a relational leader. So, the tools that I use mostly are talking to people and learning people. The parents that I have in the school, a lot of them own their own businesses. A lot of them have been in the region. And so it’s a matter of really getting to know. Again, it’s not just I’m not just here to get to know my students, but it’s also the families here. And so, getting to know the families that are here, I get to network with them throughout the school day and hear what they’re doing and where they are. And they’re giving me advice. I’m giving them advice. So, my community here at the school doesn’t just stop with my students. It also extends to the parents as well.
And so that is kind of the largest networking that we have.
What inspires you?
To me, the kids. It sounds so cliche. It really, really does. You know, every educator will talk about that. But I just enjoy the joy that a small child will find out of the silliest little thing. You know, they’ll they will find a joke. Like, why did the chicken cross the road? A joke. And they just laugh the belly laugh that will come out of a child. And so, when I’m when I’m having a challenging day, if I’m, you know, reading over emails, and there just seems to be a problem after a problem, or I’m having a challenging day, I typically pause. And I walk out of my office purposely; I start walking around the school. And I just remind myself why we’re here.
I interact with the students, I have silly interactions, we laugh, we talk. And it’s a good reminder of this is what motivates me it. I just I love the joy of a child. And it helps me get through any of the hard days that we have here.
Has being a teacher helped you become a better parent?
It definitely has, I think it’s actually the reverse. I think being a parent has helped me be a better teacher, and better educator because before I was a parent, I mean, I logically understood, of course, that the child and the mother and father have that deep connection. Of course, you understand that. But it’s something completely different when you have that connection yourself.
And so whenever I’m dealing, even if I’m dealing with a teenager who’s having a challenging moment, let’s just say, and I’m constantly reminded that this teenager is somebody’s baby, there was a moment when that baby was in their arms and was crying or had a fever, and that parent worried over them, and was scared for them. And, and I put myself in those shoes. And even though the teenager might be causing me challenges, I have that in my head, which again, goes back to that ethics of care.
But I think having children has made me a better educator.
What advice would you give to other people aspiring to become a teacher?
So, one of the things I challenged with myself is feeling like I can do this, and I earn this and what I have to say is valid. And that was something I, I struggled with for a long time.
And what really came out of that is what I have to say is valid. And so, what I’d say to other future women leaders in whatever business is, have confidence in yourself that what you have to contribute is valid. And I think I spent a lot of time second guessing myself and saying, well, maybe, you know, maybe not, I won’t contribute to that. I don’t know if that’s appropriate, or I kind of take a back seat and let other stronger voices take over. But once I really crossed that threshold, I realized, no, what I have to say really is valid. And so it’s just go fearlessly into the night and what you have to say is valid.
What future aspirations do you have?
My career. So again, in October of 2026, I will, with all the luck in the world, I will get my Doctor of Education. I do plan on continuing that scholarly aspect of my career. And so I’ve already connected with one of my former professors, a publisher. And so, he and I have already talked about writing a book about my parents’ legacy and writing a book about the school. So, I really think that’s going to be my next venture.
But then getting the word out about the school, it’s one thing to write a book and then, you know, put in a small publishing company and having, I don’t know, a couple hundred people purchase the book. But to get the book out there, I would love to travel. I want to go back to conferences. I want to explain our school and our system and the amazing things that we do here. So that’s kind of what I see myself personally doing. And then within the school itself, it’s always focused on refinements.
After year after year after year, it’s what can we tweak? What can we refine? And so, the next few years, we’re really focused on my high school program as to how do I refine it? How do I highlight our uniqueness and really showcase what we can prepare our students to do? And so, there’s no big sweeping changes. But we’re doing some building changes. So, we’re doing a gym renovation and we’re doing a high school lunchroom renovation. We’re changing it from more of a cafeteria into a lounge for my high school students. We’re changing the staff room.
So, the physical building will go through some larger changes, but the programming will be about refinements and not large changes. That’s amazing.
What’s your school’s thoughts on field trips and what’s St. Jude’s sort of philosophy on that?
Yeah, that experiential learning is important because what you learn out in the world is deeper than what you learn sitting in a classroom. So, I love field trips and I love the way that they connect, but I want them to connect to whatever content, what we’re talking about. So, my kindergarten grouping, they always go year after year, they go to the Butterfly Conservatory. That’s always a good field trip. But the teachers spend the first month, they, we bring in butterfly larvae and then we grow butterflies. They go through the whole life cycle of the butterfly. We release the butterflies and then we go to the Butterfly Conservatory. That’s just one example.
But I love it when teachers will take what they’re learning in the class and then connect it with something outside. So, you would see field trips through, I had a group just go to Activate and it’s a fun program. It’s like the kids just thought, well, that was a fun day, but it ended up being all about our leadership program.
And so, they were learning communication and the teachers that took them to Activate were really focused on building those, continuing those leadership skills. I have a grade eight and grade nine leadership conference that we go to Muskoka Woods. And so again, the students, it’s guised as this is going to be a fun opportunity, but there’s learning embedded throughout the whole process.
And so, I’m, yeah, I really love taking the kids outside of the building.
Tell us more about your traditional approach to teaching
Everything we do here is very purposeful. And so, when I’m taking a parent around and I’m walking around, often a parent will ask about technology and our use of technology. And I, I joke a little bit and I say, it’ll feel a little like 1994 here. It’ll feel like maybe 1986, because you really won’t see the technology.
So, from kindergarten to grade five, it is paper and pencil. The students are learning from textbooks. They have a speller. Students are taking notes from the board. It’s study after study, after study, a decade’s worth of knowledge or more has proven that when you take a pen and you take a pencil and you put it to a piece of paper and you use your hand and the motions of writing the synapses that are created are so meaningful and deep and connected to memory. And learning is far greater than when you take and you click on a keyboard and you look at a screen.
It is so, there isn’t the same depth of connection. And so, there’s, there’s been a time or two where an apparent has walked around and like, well, gee, it’s 2026. How come you don’t have smart boards? How come you don’t have, you know, all laptops or tablets as like, it’s done very, very purposefully because up until the age of 25, a child’s brain is still developing. And so, I need to provide every opportunity to develop all those incredible connections and synapses until they hit that age. And there just isn’t enough research to say that the traditional old school ways are not as good as the new ways. So, we are still very purposeful, very traditional in that aspect.
Where can listeners find out more about you?
So, they can find me by going to sjsh.ca. I’m the principal, and you’ll see my principal’s message and my email is located there. Of course, I’m on LinkedIn too, if a person wants to look me up. As of the summer, they could find my doctorate research on the Western Repository. And so that will be published, again, with luck, it’ll be published at the end of August 2026. And so, they’d be able to find my dissertation there. And then just we have a parent Facebook group, the school’s on Instagram. And whenever they message the school through Instagram or Facebook, it’s directly to me. So, if I get a message from a parent or a question online, I get it directly on my phone. So that’s directly contacting me.
*This interview has been edited for length and clarity.
