Josh Windsor: Principal at Eastwood Collegiate
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Josh Windsor: The Visionary Principal Redefining Education
When we think about transformative leaders in education, Josh Windsor's name stands out. Currently the Principal as part of the Waterloo Region District School Board at Eastwood Collegiate in Kitchener, Ontario, Windsor has devoted almost 25 years to revolutionising the way we view teaching and learning. His career is a compelling narrative of resilience, adaptability, and a commitment to fostering meaningful change in students' lives.
From Humble Beginnings to Lifelong Resilience
Josh’s journey began in adversity. After losing his father at the age of five, he grew up witnessing the harsh realities of poverty and the challenges of navigating an unstable household. By 17, he was living independently, balancing school and work—a period that shaped his deep empathy and understanding of the struggles many students face today. These experiences, combined with early jobs in group homes and with Family and Children’s Services, ignited his passion for supporting youth.
A Path Forged Through Coaching and Community
Initially pursuing a career in marketing, Windsor found his true calling through coaching. By 19, he was coaching high school rugby, a role that allowed him to witness firsthand the profound impact a mentor can have on young lives. This passion eventually led him back to education, where he saw an opportunity to merge his leadership skills with his commitment to youth development. At 29, he took the leap, enrolling in Teachers College and embarking on a mission to inspire change in the classroom.
Reimagining Education Through a Coach’s Lens
For Windsor, teaching is fundamentally about development—a philosophy shaped by his years as a coach.
“Coaching is really about building skills over time,” he explains, emphasizing the importance of growth and progress.
Windsor believes that traditional assessment methods, which rely heavily on time-based testing, often fail to capture students' true potential. Instead, he advocates for approaches that evaluate growth through a mix of observations, conversations, and performance.
His leadership style extends to mentoring teachers, encouraging them to reflect on their practices and continually improve.
“The single most important factor in a student’s success, other than parental involvement, is the teacher in the classroom,” he asserts, highlighting the pivotal role educators play in shaping students’ futures.
Navigating the Challenges of Modern Education
In an era dominated by technological advancements and social media, Windsor is acutely aware of the challenges educators face. From managing the mental health impacts of social media to integrating AI and e-learning into traditional systems, his approach is both proactive and thoughtful. Windsor’s advocacy for hybrid learning models underscores his belief in balancing technological innovation with the inherently social nature of education.
His stance on cell phone use in schools is particularly compelling. Recognizing the negative mental health effects of excessive social media consumption, Windsor has taken steps to minimize these risks for students.
“As a leader, I feel responsible for creating an environment that prioritizes students’ well-being,” he says, emphasizing the importance of engaging parents and students in meaningful conversations about the role of technology in their lives.
A Legacy of Empowerment and Progress
Reflecting on his career, Windsor offers advice for educators starting their journey:
“Don’t be afraid to ask for support.”
He stresses the importance of collaboration, both in addressing student behavior and in fostering professional growth among teachers. His belief in the power of teamwork and shared responsibility has been a cornerstone of his leadership.
As Windsor continues to shape the future of education, his story serves as a powerful reminder of the impact one individual can have on countless lives.
From his early struggles to his current role as a principal, he exemplifies the transformative power of resilience, mentorship, and a relentless commitment to progress.
Josh Windsor isn’t just an educator—he’s a visionary redefining what it means to teach, lead, and inspire.
Discover Josh Windsor's story on the latest episode of Educators of Today with Ziyaan Virji.
Listen now on Spotify, Apple Podcasts or Youtube and be inspired by a principal who’s redefining leadership, one student at a time.
Educators of Today with Ziyaan Virji is a podcast that dives into the stories of principals, superintendents, and educators shaping the future of learning. Each episode explores the challenges and innovations in education, from mental health and student agency to leadership and school culture. Whether you're an educator, administrator, or advocate for education, this podcast offers actionable insights and inspiration to create lasting impact.
Hosted by Ziyaan Virji, a 23-year-old award-winning keynote speaker and changemaker, the show combines his global perspective with the expertise of leading educators. Ziyaan has delivered 200+ talks in 7 countries, including TEDx, the United Nations, and the Global Education and Skills Forum, inspiring over half a million people worldwide.
Contact Ziyaan for speaking engagements that inspire schools to foster student leadership, mental health, and impactful education.
Transcript
[Intro Music fades]
Ziyaan: Thank you so much, Josh, for coming on the Educators of Today podcast! You're actually our third guest on this new podcast that we've started, and yeah, super excited to go right into it. I know you've had a very long career in the education space, but before that, you spent some time in the marketing world. I'm curious to learn, if you had to go to the very early days of you growing up, are there any experiences or stories you remember from your time as a young person that has shaped who you are today and all the work that you do?
Josh: Yeah, I mean, I guess I had a bit of a difficult childhood. My father died when I was 5 years old, and my mother was quite young—she was 22 with two children. We did not have...my father didn't have life insurance, we didn't have means, so we lived, I would say, in abject poverty for a while. My mother remarried quite quickly, and that relationship was probably not a healthy relationship for many reasons. So I did kind of struggle through some of those things in my youth. When I was 17, I lived on my own, finished high school by renting a room from somebody and working, trying to do all of those things. So I would say building resilience through some of those experiences allowed me, as an educator... I mean, I also started working in places like group homes and Family and Children Services at quite a young age. I did that all through university, and had a full-time job while I went to school full-time as well. And those experiences allowed me to recognize and understand what some of our, I would say, students with the most need require from us to help them in an education system that is rife with barriers to their success. So, I was one of those students, and so for me, it hits home when I try to help the kids that need my help the most.
Ziyaan: Yeah, no, I appreciate you sharing that. And I'm curious to learn, were there any teachers or educators or people in your life at a young age that did offer that helping hand, or that support, or paved the path for you? Are there any, just on top of your head, that you can remember that you are grateful for?
Josh: Definitely in high school. Two in particular that I think of. One was a history teacher, and one was a coach. My history teacher, Mr. Alt, he probably said the most profound thing that I will always remember to me because I was a bit of a, I would say, a rebel. I was walking that line between whether I was going to conform to society's rules or not, right? Because seeing people around you with a whole lot more than you have often brings you to kind of thinking about different theories—things like socialism and communism. History was interesting to me as a young person because capitalism wasn't something that I was... you know, I didn't have the advantages that other people had trying to be successful from an economic perspective in a capitalist world. So he said to me one time, he said, "You realize that in order to change the system, you have to be part of it." And for me, that became a beacon that allowed me to then think about how I can create and foster change by not being outside of those processes that we need to be involved in in order to be leaders and create change, right? So that was really something that was profound to me at the time, that shifted my way of thinking. And to think back now, because it probably happened, I think, probably in Grade 11 when I was about 16... to think back now that I still remember that conversation, I think, made it really important for me. And then the other person was a coach who... I was a rugby player in high school, I played volleyball, basketball, and rugby. So I was somebody who was involved in athletics, and he told me that I could probably go play rugby at university. And that was... I wouldn't have never believed that if he hadn't told me that, and I probably would have never gone to university if I didn't go because I wanted to be a rugby player. I learned the importance of education, and I recognized that value while I was at school, but I went to school because I wanted to be an athlete.
Ziyaan: Yeah, so that's an interesting pathway, you don't often see that from people who end up in education.
Ziyaan: Yeah, no, 100%. And yeah, I appreciate you sharing both what your history teacher and coach said. I feel like, uh, I always reflect on how in the school setting, it's such a huge privilege that you can shape someone's life, and it's the little things that you do. I'm sure the history teacher or the coach probably doesn't remember it, but you do until today, right? For me, I remember one thing that I remember from my Grade 3 teacher was, I used to always submit my math homework late, and she would always say... I would always say, you know, "I'm going to submit it tomorrow, I'm going to submit it tomorrow." And she's like, "Tomorrow never comes." And at the time, I didn't think too much about it, but this is something I remember until today because now my whole philosophy has been about, if you want to start something of your own, if you have a specific passion that you want to pursue, you can't wait until tomorrow because tomorrow never comes, you can start today. And so it's very interesting that you mention those things, and I really like this whole idea of, you know, if you want to change the system, you got to be part of the system. And it sounds like as part of your journey, you have already been doing that. I'm curious to learn, so you mentioned playing sports, sports was a big part and even going to university as part of that, what was that time like for you at university? Yeah, tell me more about some of those experiences.
Josh: I worked full-time while I was at university. I had some different roles working with, mostly with kids, youth at risk, I would say, were where I focused on. So my one role at Family and Children Services here in the Waterloo region, I worked 10 at night till 9:00 in the morning. I worked in an intake and assessment center where we had teenagers that lived there, usually for short periods of time. They could be brought in in the middle of the night, so it might have been a kid who was living on the street, it might have been a kid who was apprehended from a home. I supported those students by helping them get to bed when I got there, and then I helped wake them up in the morning and get them to school, and then I would go to school myself. When there weren't things happening... I had the job, it was called the "sleep job," so that's why my hours were longer, there was somebody who was awake. So I was able to do that, and the second component of that role was I did foster parent in-crisis intervention. So if there was a nighttime issue where a foster parent of a child that was a ward of the state had issues, I would go in and try to do mediation with the foster parent and the kid. And if we couldn't come to some agreement to resolve the issue, then I would, at times, take the adolescent with me back to the home, get them a bed so they had a place to stay for the night. So it was an interesting role, but it allowed me then to pay for my education, pay for all my living expenses, and then continue to play rugby at university. And in part of that... part of those years, I was also the president of the student union. So I was very busy, but I found staying busy kept me focused, and I was able to then juggle and balance all of those things. It provided me with a pretty high threshold for work also.
Ziyaan: Yeah, yeah, and it sounds like a lot of those experiences, like, you know, you're working with parents at that age, you're working with young people at that age, was it... was there a certain point where you were like, "I want to pursue a career in education?" What...
Ziyaan: What was the point where you realized this was something for you?
Josh: So I worked at the Children's Aid Society full-time, and then part-time again when I finished university and graduated. I then started my foray into kind of some different businesses, mostly in the area of sales and marketing. I was doing that for probably four years in various roles, was the director of sales and marketing for what I would consider now to be a startup software company, and I just wasn't really being fulfilled. So I had always coached—I started coaching high school rugby at the age of 19 when I was a first-year university student—and so coaching was really a passion. Working with kids through those other experiences was something that I knew I was relatively good at, so I was pretty effective. And so I decided I wanted to mirror that love for coaching with my capacity to work with adolescents, and education just seemed to be the right place. So I went back to Teachers College at the age of 29 and then started my journey into education shortly thereafter.
Ziyaan: I love that. And you mentioned, obviously, coaching, and you had been coaching since 19. What parts of coaching would you say you bring to your current role, more in terms of how you work with young people?
Josh: I mean, coaching is really development, right? So if we think about things from an education perspective, you're teaching all the time as a coach. And what I would say is when we start to think about education and the experiences that we've had, especially as we think about things like assessment and testing, we realize that if we take a coach's approach, we are trying to build on skills to develop an individual to be able to perform. And in our current education system, we've started to shift our thinking around what I call time-based or situational testing. Because that moment in time is really only that moment in time. And if we think about it from the perspective of athletics, or even music performance, any type of performance, we really know that those performances change every time somebody tries to perform. So, you know, the basketball player that scores 35 points today has a different defender on them tomorrow and only scores 20. That player isn't necessarily a worse basketball player, it's just in that moment, at that time, they've performed not as well as they did the last time. And we know the factors that impact that. As we think about the educational perspective, and we think about, like, teach, teach, test, then average those tests together and maybe throw a final exam in there, we recognize that each of those moments were extracting data, but it isn't necessarily that kid's best work or that individual's best work as we do the testing, right? So when I think about coaching from the perspective of performance and achievement, we look at that growth over time, and that's really what's important, right? We don't... we don't look back on, you know, uh, LeBron James's performance in 82 basketball games, we look at what he does in the playoffs. And so how do we get ourselves to a place where we can look at education from the perspective of finding the best examples of performance of work? Looking at... we call it triangulation, so using conversations and observations to assess students, as well as any type of product that they might hand in. And when we think about the needs of our society from the perspective of a changing workforce, or the needs of a changing workforce, we really have to look at many different skills than we used to, right? I mean, I can... I think you're going to ask me some other questions, so I can go into that a little more later. But from a coach's perspective, that's what I'm always looking for my teachers to be able to do. But that's what I do with other people. So as a mentor of teachers, and even my vice-principals, what I'm looking to do is help them get better all the time. So situationally, we kind of debrief and reflect on the things that they're doing in order for them to go through a process of evaluating whether or not they're being effective. Right? So if I have kids in a classroom that perform poorly on a test, my first question is, "What can you do differently to make sure that doesn't happen again?" Right? And oftentimes, we don't look internally into those things. So I'm looking to have my teachers reflect on their performance because it does impact what their kids can do. And if you look at research, the single most important factor in a student's success, other than parental involvement in their education, is the teacher in the classroom. And so we know that to be true. So the only way we can impact performance and achievement in a classroom is to make sure that our teachers are getting better at doing what they do.
Ziyaan: Yeah, no, I love that. There's a lot of good stuff you mentioned there. I know earlier you, when you were talking about coaching, it reminded me of one of these things my mentor says, the idea around, you know, "the currency of success is progress." And you talked about growth over time, right? And this idea of triangulation, looking at other factors. And then towards the end, you talked a lot about this idea around how do you shift the responsibility, and instead of blaming the students for their performance only, how do you look at the teachers and how they could improve their performance. And so, um, yeah, that's some really good stuff, and it sounds like you're really also passionate about it. I know you did a lot of work in teacher and professional development as a consultant as well. Curious to learn, tell me more about that. I think I saw something around, like, district e-learning. I'd love to hear more about that as well.
Josh: Yeah, so one of my roles as a consultant was professional development for department heads. So we have school department heads in subject areas. And then the other part of that role was kind of to support e-learning when we were... that would have been back when we were right at the beginning of e-learning implementation. One of the real lessons with regards to e-learning is recognizing that in education, we have to be really careful about trying to teach the modality at the same time as we teach new content. So if you look at success in e-learning, lots of times the unsuccessful individual is trying to learn the modality of e-learning—so how do I learn through this system, right?—and then layering on the content. And when we do both of those things, we see that people are less successful. So as you see the success grow for e-learning students, you'll recognize the characteristics that make them successful. So they're learning on their own quite a bit, so they have to be someone who's able to think through content and problems, but then also advocate for themselves if they have questions, right? So the capacity to sit in a classroom and have a teacher be able to intuitively understand and recognize whether you're being attentive, or based on body language whether you understand a concept, is very different than you sitting in front of content on a screen without any of that social interaction, right? So the teacher has no idea if the student's learning until the student provides some product around the learning, or some demonstration of learning. And so if you have an individual that A, isn't able to navigate the system, which is the modality, but B, is grappling with content on top of that, they're almost always unsuccessful. Yeah, and then you'll see that success increase as they learn the modality, because then it becomes only struggling with the content that they have to use their mental capacities for, right? Makes sense. I don't... I don't know that we will ever get to a place where all students will only be learning, I would say, asynchronously through e-learning, right? I think there's a real demand for some synchronous learning digitally, and I think we should probably always be thinking about a hybrid perspective when we think about education. Obviously, there are circumstances where some students will only be able to access certain curricula because......they're remote, right? So if I, you know, if I want to access any content from somewhere that's very far away for me, right? Or in a school that's very far away from me, I'm not going to be able to do that unless I move. And so there is a place for that, but I believe true learning is social. Yeah, I'm a constructivist, and you can't isolate content from the skills that are needed to be able to collaborate, be socially effective, interculturally effective, creative, be able to be collaborative in problem-solving and thinking. Those are such important things that we do as humans, that to suggest just looking at content on the screen is going to help me become successful in this world is probably unrealistic.
Ziyaan: And I appreciate you sharing that. I'm curious to learn, just because we brought this up and you talked a lot about the modality of learning, what's your thoughts on... right now, there's all these different technological advancements with AI, with obviously social media, with virtual reality. There's all these different advancements. What's your thoughts and take on that and how that affects learning in this day and age?
Josh: I think it's really important for us to explore new technology. I think in, especially in the public education system, we are so far behind technological advance that oftentimes we're struggling to even understand it, right? And so if I think about the public education system in the Western world as a colonial structure that's been altered to meet the demands of a 20th-century industrialized society, many of the residual structures in our system, especially those embedded in legislation, are very difficult to change. They provide for a rigidity that directly counters the flexibility desired in a rapidly changing society, right? And technology is a big part of that. So we're bumping up against legislation, policy, procedural rigidity, other barriers like risk management and liability, right? That stifles things like creativity, improvement cycles, outside-the-box thinking. And we're faced with those barriers on a regular basis. The use of technology, although it becomes really important, we also have... we walk this fine line between protecting children. And I think when you talk about social media, in particular, and looking at the very recent research on the impact of mental health... on mental health for adolescents and teens, that social media and the widespread use of cell phones has had... it's such a difficult thing for us to now grapple with. We're trying to walk back some of these things that have become embedded in our society and supported through our capitalist approach to, I mean, I think everything, right?
Ziyaan: Yeah, it's really difficult.
Josh: And so as a leader, I feel like I have a responsibility to minimize risk for students. I wouldn't let students smoke in my bathroom, or vape in my bathroom, or be on illegal drugs in my school, but I'm allowing them to use something that I know directly harms them. So we've started to take steps against that. And I don't know if you saw my podcast that I did with the doctor that I've had engaging with, um, engaging with some of these issues, but her perspective with regards to the massive increase in mental health issues in teens in her medical practice and my understanding of the new research has really been impactful in how we're trying to deal with this issue in a school.
Ziyaan: Yeah, no, it completely makes sense. Something I am very interested and passionate about is the use of social media and how that affects... even from a scientific perspective, you look at dopamine, right? And you look at how scrolling on social media for an hour has the same sort of effect as taking a drug. It has that addictive nature. From a dopamine perspective, you have the same level of... and so it's very interesting to see. And unfortunately, society is built in a way, and a lot of these platforms are built in a way, that makes... you're sort of forced to use it. And so how do you, as you say, tread that fine balance between still participating in society and exploring technology and the benefits of it, but also keeping in mind the negative effects, especially at a young age when you don't fully understand what it's doing to you, right? And so yeah, I'm really glad you mentioned that. Can you tell me more about... I know there's also, like, a recent government mandate, but a lot of your... like, even the podcast that you did was even before that, and you've been very proactive in that. For other educators that are listening, what are your recommendations or takes on, or advice on, that specific piece?
Josh: Yeah, I mean, I think the first thing that I would recommend to anybody is you're entering a brave space, right? And you have to ensure that you have the confidence to be able to have conversations, I would say especially with parents and students, around this issue. And doing some homework around the research is really important. Like, I will talk about research with parents and help them to understand that their need to have 24-hour contact with their child should be looked at in multiple ways. You know, when I talk about perspective, I don't judge people for their values, but I do say, "Have you thought about it this way? So have you thought about the fact that every time your child has a problem, they can connect with you and you'll solve the problem for them? That may, at some point in time, make them so dependent on you that when they become an adult, they're going to have difficulty solving problems, right?" And so when we think about theories like gradual release of responsibility in decision-making, we have always put ourselves in situations where we're allowing children, as they develop, to make certain decisions, right? So I might let a 5-year-old decide what shirt they're going to wear because I've selected all of the shirts that they own, and I know they're going to be appropriate for them to wear in a social setting. So I say, "Which shirt would you like to choose?" And you get that child then involved in decision-making, which helps them to build confidence and resilience and all of those other things. And we gradually release those decisions to children and then adolescents. But if every time we go and we ask... we have to ask somebody else what we should do, then we never develop that decision-making capacity. And then when we get ourselves into a situation where we have to make a decision, especially if it's in a crisis situation or a safety situation, we often can make poor ones, right? And I always liken it to... you know, I use Google Maps for a lot of things. I never used to have to use Google Maps for anything, I could find my way to places, and now I rely on it. But if Google Maps tells me to turn left and go off of a pier into the water, you know, I can make the decision that that's probably not a good idea.
Ziyaan: Yeah, not sure. Because you hear about things in our society where people have done stuff like that, right?
Josh: Yeah, right. They've turned into a situation that becomes unsafe because an app of some kind told them to do it. And when we think about that, what we do is we recognize we're creating dependence around decision-making and risk-taking that we need everybody to be able to have in order to be successful as individuals. Yeah, so having that conversation with parents, right? So I did have, at one point in time, and this was a number of years ago, I had a mother who was facing cancer. And because... because of that, there was some codependence between her 16-year-old daughter. At one point, I just said, "Listen, do you trust me to give you some advice?" And...
Josh: ...she said yes, and I said, "What I'm going to suggest you do is you tell your daughter she is not allowed to contact you during the school day." Because this mother would be getting treatments at the hospital and then having to answer calls from a daughter who was frantic about something happening in a classroom, which really wasn't that big a deal. But because of the anxiety around cancer and what's happening with my mom, there was that codependence. And then the mother would be very upset, call the school, be super anxious and frantic about that conversation. And so I said, "You know, for the well-being of both of you, why don't you make a rule that you'll talk about it at dinner, unless it's an emergency?"
Ziyaan: Makes sense.
Josh: And then they began to kind of implement that, and the mom called me back about a month later, and she said, "Thank you so much, that was probably the best piece of advice I ever got. Because now she's learning to deal with those issues by herself, and I'm not feeling like me dealing with this significant medical issue and me thinking about whether or not I'm going to survive is putting me in a really difficult situation on whether or not my daughter's going to be relying on me if I'm not here."
Ziyaan: Yeah, no, makes sense. Yeah, there's a lot of good stuff you mentioned there. Talk about gradual release of responsibility, I've never heard of that, but it sounds like you iterated that very well. And then you also talked about... that's Vygotsky, so...
Josh: Yeah, so, like, educational research, Vygotsky is one of the kind of founders of constructivism, so pretty famous.
Ziyaan: No, I love that, I love that. I know we're almost out of time, I feel like we could go on forever, but I guess one last question I had for you was, you have, obviously, it's I think almost 25 years in the education space, right? As a coach, as a teacher, and now in leadership. If you had to go back to year one, what advice would you give to yourself, for someone that's... you know, as someone that's just starting out in this space?
Josh: Yeah, I mean, education has changed so much in that time, but I think the one thing that still rings true to me is not to be afraid to ask for support and help. When I think... I think as educators, the really difficult part about being an educator in, I would say, K to 12 is that you go from being in school to being probably pretty good at school, right? Because to get a university degree and then to get into teaching, you have to be pretty good at school. And school is a game, like anything else we play. When you're good at school, you believe coming into education that every child is going to be like you, right? Realistically, only 25 to 35% of our kids ever go to university. Yeah, so most of the kids you're going to teach are not like you. And when we kind of have these middle-class values around many things in our society, we fail to truly understand how some of our students need to be treated in order to be successful. And then we get into those issues around blaming. Yeah, so we blame kids, and we blame families, and we blame society, as opposed to thinking about where the efficacy really lies, and that's in what we do every day as educators. Yeah, it's complex, it's difficult. And, you know, teachers, for the most part, are incredible people. I've never met somebody that didn't love kids or want to be where they are. I've met lots of people that have become jaded over time, but nobody has ever come into this profession thinking, "I don't want to be here." They've made that conscious decision and choice. And so I see so many young teachers struggle because they're afraid of being judged by people, like, people in a principal position, right? They're going to think, "I'm not good at what I do if I ask for help." But the reality is, in order to really deal with many of the difficult-to-serve people that we deal with, we need to work as a team. Yeah, and so I communicate that to my new teachers all the time, like, asking for behavioral support from a vice-principal is not a failure in your classroom, right? Allowing behavior to drive what you do in the classroom and to remove a good learning experience from other students is a failure in your classroom. Right? Getting support for the kid that needs the behavioral support is actually really important in order to support all of the other students there.
Ziyaan: Yeah, yeah, no, makes sense. You couldn't have said it better. Yeah, and not being afraid to ask for help to do that. Honestly, this has been such a great conversation. I feel really energized. I can tell how passionate you are about the space, and we went down a bunch of different rabbit holes, and so I've learned a bunch of new concepts. I appreciate you taking the time. Yeah, this was... I feel really energized, and thank you so much for sharing.
Josh: You're welcome.
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