About Claire Kelly
Claire Kelly (@ClearGreenDay) serves as Assistant Head of School: Student Life, at Appleby College, an independent grades 7-12 school in Oakville, Ontario. Her responsibilities include leading a portfolio of outstanding student-centric experiences in Arts, Athletics, Service, Student Leadership, and Boarding Life, supporting coaching and leadership development experiences for faculty and students, and facilitating opportunities for student growth and school culture.
Claire teaches English and AP Capstone Research, where she has supervised over 70 academic Research studies, an array of which have been published in external peer-reviewed journals. Claire earned her PhD from OISE/UT (’19), in Leadership, Higher, and Adult Education.
Her interests include leadership development and organization change, career patterns, and gender representation, and Independent school headships in Canada. Claire has co-led affinity groups for women leaders and taught the Women in Leadership module each summer since 2019 with Canadian Accredited Independent Schools (CAIS). She has written three children’s books (Rubicon) that combine her love of travel with her passion for Arts, Literature, and Social Sciences, all designed to cultivate young readers.
Claire loves to run, paddle, dance, and play sports. Her love of learning continues beyond the classroom with hobbies such as learning guitar, enjoying music, and travelling. She lives with her husband, Nicholas, also, an educator, two sons, Julian and James, and mini-Doodle, Piper, on the beautiful Appleby campus.
Connect with Claire: Email | Instagram | LinkedIn | Twitter | Facebook
Listen Now
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Resources Mentioned
Leadership, Higher, and Adult Education – OISE/UT
Canadian Accredited Independent Schools (CAIS)
Student Leadership – Appleby College
The Transcript
**Please note that all of our transcriptions come from rev.com and are 80% accurate. We’re grateful for the robots that make this possible and realize that it’s not a perfect process.
Sam Demma
Welcome back to another episode of the High Performing Educator podcast. Today I’m very excited, we have a special guest, Dr. Claire Kelly. Dr. Kelly, please take a moment to introduce yourself to everyone who’s tuning in today.
Claire Kelly
Hi Sam, it’s great to be here. Please call me Claire. I am a teacher going into my 25th year of teaching, which is amazing to me. I don’t know how that happened. And I am currently an assistant head of school at Appleby College, and I’m head of student life there. So I work a lot with students and very closely with all aspects of the student experience.
Sam Demma
When did you realize in your journey as a student and young professional that you wanted to work in education?
Claire Kelly
Yeah, that’s a great question. As in like what got me into this work?
Sam Demma
Yeah, well, everyone has a very different pathway. Some people tell me they built dollhouses in their basement and taught the toys class. Some people told me that their family worked in education and they followed that pathway. What was your journey into working in schools?
Claire Kelly
Yeah, I guess, you know, ultimately, I started, I became a teacher because I love working with students, with children, with adolescents. You know, unlike many people, I love adolescents. I think they’re really amazing and they have so much to teach us. So, but yeah, going back to the start, I guess my father was a professor, my aunt was a school teacher, so I had some familial influences. However, yeah, I think, you know, teachers in high school certainly left strong impressions on me. I had some great teachers, they helped me better understand myself. I was also an athlete for much of my schooling. I spent a lot of time out of school in some ways, but a lot of time with coaches. And I loved working with people to accomplish goals, like whether it was as an athlete or as whether it was like individual athlete or on a team. I just loved being able to make those connections through sport. And I love the drama that you get from, you know, going through a game together or I was a figure skater for a long time, so like a four minute solo and all the preparation and all the people that go into making that happen. Yeah, and I think, you know, ultimately I like movement, I like variety, I love that teaching is never the same day twice. And we have this incredible ability to meet so many people, which is incredible. And I love the rhythms of the days and the years. So, yeah, I have to say I’m really happy where I am. I’m really glad I chose this. It just seemed like a natural part of – natural place I would end up.
Sam Demma
The rhythm and changes and movement as a school teacher are very vast. I’m sure it’s very similar with the role you’re in right now in student life. What does being the head of student life look like? What is the day-to-day in this position currently, what does it entail for someone who’s never been in that position or doesn’t know too much about it?
Claire Kelly
Yeah, that’s a great question. It’s an incredible role. I absolutely love it. I’ve been, this is my third year in that role. So I’m relatively new and it involves arts, athletics, service opportunities and running the co-curricular program for students, which is at our school is mandatory. So we have a very robust co-curricular program with, you know, approximately 60 different opportunities for kids. We also have a student leadership and a fantastic student leadership program with, you know, so many formalized responsibilities that are graduated really from grade 9 to grade 12. And then we have the Boarding Life program, which is, you know, our school is a day school, but it’s also a boarding school and we’re one of the only schools in North America that has mandatory boarding program for all their grade 12 students, so they move on campus and then they and then they get they stay and they live that year and understand you know a little bit more about themselves and what they need to prepare for classes and get ready in the morning and you know feed themselves and all sorts of life skills, as well as a fantastic university prep experience. So, a lot of our parents will say things like, you know, this is almost like the dress rehearsal for going off to university, which is really an incredible opportunity. So student life looks like having a sense of really getting to know students really, really well from breakfast in the morning through study in the evenings, certainly at this school, and having a good sense of what they need and what drives them to be the best they can be.
Sam Demma
I felt very honored that I was able to visit the school and tour campus when it was around Thanksgiving time and I had this beautiful potato lunch. And it was delicious. It sounds like there- I love this thing.
Claire Kelly
There’s an exo group that runs our dining hall. It’s incredible.
Sam Demma
It sounds like there are so many unique opportunities for the students, even the staff, as a part of student life on campus. One of my favorite authors is a gentleman named Jim Rohn. He talks about the seasons of life and how they can be tied to the seasons of business or just like the idea that there’s rhythms to things. And he has a phrase, he says, you know, after opportunity is always adversity in some way, shape or form. You know, with lots of opportunities, there’s also challenges. And I’m curious, what are some of the challenges that you think you’re faced with right now at school or on campus?
Claire Kelly
Yeah, that’s such a great question. How long do we have? Yeah, I mean, there are always challenges. So we could name off. There are some significant challenges that our students are facing. There’s eco-anxiety, there’s mental health, there’s DEIB, how to better integrate and have a more just world. There’s Indigenous reconciliation, especially in Canada. It’s hard not to think of that as top of mind. University admissions, that might be not as grand a scale as some of the other challenges, but it’s certainly a significant landscape for our students and it’s a very changing landscape right now and with the latest news from federal government and it will be interesting to see what that means in terms of the impact even on undergrad students and the available programming. So, kind of watching that closely. Socioeconomics, you know, it’s really hard to buy a house right now. It’s hard to buy a house anytime, but certainly it’s very challenging for any student growing up in this generation is looking at some big challenges, how to fund the life that they want to lead. You know, increasingly VUCA world every time I turn on the news. So, there are some big, big challenges.
Claire Kelly
I guess how do we deal with that? Well, you know, day by day as much as possible. We hope there’s a strategic plan of some sort. And that helps. And like ultimately, like, I guess a lot of people have seen opportunity in challenge and there is always opportunity in challenge. You know, the Dalai Lama talks about that. Whenever there’s a challenge, there’s an opportunity to face it, to demonstrate it, to develop our will and determination. I’d also say, like, as school teachers, we’re kind of right in the rhubarb. We’re dealing with some of this every day because this is the student world. And I’d say that, you know, humbly, we continue to work on these. We have time, we have space, and we have these incredible moments of dialogue that we get to sit and work with a huge collective of youth. And that’s a pretty magical place. So we learn from them, they learn from us. It’s a pretty neat thing. So and then, you know, we have these great opportunities as well, certainly at our school, where we bring in highly motivated and motivational speakers like yourself. So that was really wonderful to have. But, you know, I think, you know, I work with some really incredible people. I work with motivated, kind, talented people, and they see challenges as opportunities to do things better. That’s really the only thing we can do is try to find the opportunity in it. We think certainly for teenagers, challenge is an inherent part of being a teenager. You’re always challenging, challenging yourself, you’re challenging other people, you’re pushing boundaries, you’re trying to find that light. It’s a pretty exciting space when you think about it. It’s like that liminality, you know, you’re in the middle of something. And it’s really essential to growth. So the question is really for me is how do we tackle the challenges and how can we have impact in our school’s culture? How can we arm these kids with the skills that, you know, they have nascent within them? How do we, how do we develop those and give them to them so that they can have an impact on their larger worlds? So I don’t know if I fully answered that, but that’s kind of what we do. I try to do everything.
Sam Demma
Yeah. I love the idea of seeing opportunities within the challenges. The same author I mentioned, Jim Rohn, he always says, we can’t change the seasons, but we can change ourselves. And if we do change ourselves, everything changes. And it’s like the challenges are gonna be there, but it’s our perception of them that makes all the difference. What of the programs you ran last year, or even in the past couple of years, do you remember having a really positive impact if there are other people tuning in thinking, oh, maybe they can consider this for their school or their community as well?
Claire Kelly
Yeah, that’s a great question. Well, as I mentioned, we have a very robust co-curricular program, so that’s pretty amazing. Students can choose from, you know, participating in a sports team or joining an all-school play, or trying their hand at robotics or design or working with seniors. We have a group, or several groups, that go out actually into the community and work with seniors and work with school children and try to find time and space to work together and learn from each other. So that’s pretty neat. Other programs that were really successful, I did mention the Student Leadership Program which certainly I’m really proud of, spending a lot of time with motivated kids gives me a great deal of hope. I think, yeah, when we talk about programming, it’s really about giving students opportunities, especially I think in that early teen time, you know, that tween, pre-teens or tween time, when they don’t really know who they are, finding time, finding space, finding people who will give them something to help them think a little bit more or discover something new. So one of the things we do pretty well at our school is we have a significant breadth of opportunity and we try to offer, we offer so much. Sometimes it’s challenging to do so, but the breadth is really to really offer students an opportunity to try something new, get to know themselves, get to maybe change their mindset about things they thought they didn’t like or areas where they didn’t think they that, yeah, give them that time to really dive in. And it’s okay if you don’t like it, it’s kind of a, it’s a very low risk, very safe opportunity. But really finding those moments to, yeah, to realize that, hey, you know what, I’m not just an athlete, I really like singing, or I want to try stand-up comedy, or I want to try to see if I can plant a sustainable garden. So how are you going to spend your time? How are you going to spend your life? That’s really it in a nutshell. So we try to challenge them through opportunities to help them discover a little bit more about themselves. And it’s pretty neat to see in a teenager’s life to change from say, grade eight to grade 12. It’s sometimes it’s, well, it’s always remarkable. And sometimes it’s really, really surprising.
Sam Demma
When you think about seeing those changes in students, what does that look like? Is it a change in behavior? Is it, they start very shy or uninvolved and the time they’re graduating the school, they’re involved in everything? What does that actually tangibly look like in your experience?
Claire Kelly
Yeah, I think that’s a great question. It is all of those things. I guess it’s a change very much in confidence, and it’s that confidence to, it’s okay to be myself, it’s okay to try things, it’s okay if I’m not cool, because actually like embracing that and recognizing that you’re trying something new and there’s a chance you could fail, that makes you really brave, that makes you really cool, ironically, right? And then it’s really neat to see the shift in students, both in terms of individual but also in collectives where they’re like, oh, that is, it’s amazing what you did. It’s incredible that, you know, you want to lead the academic council. Good for you. Let’s all jump on board because you’re doing some really neat things there and I want to be part of it. And I think that’s something that comes with confidence. I think, you know, grade seven, grade eight, grade nine can be tough. Those are tough years for students. And we need to give them a lot of support. We need to remind them that they should be trying new things. They don’t know everything about the world yet and challenge them to engage. And I think as long as we can keep them engaged and keep them talking and keep them with an eye towards the future, that they can really start to thrive. Yeah, so I would say that students… I’ve seen… well, last week, let me think of an Last week I was at a karaoke show that was run by some students and we had significant participation from students in the evening, it was a fundraiser, and they had to do a little bit of preparation. And we must have had 12 acts that were coordinated, planned, choreographed, and I guess the thing that struck me, and several of the other teachers there, if I can speak on behalf of a few of us in the audience was some of the students that I saw in grade 9 who were quiet and shy and reserved and really trying to find their place. We’re up there in the middle of it all, taking the lead, feeling comfortable, really owning that stage and you know that would be, that’s a very visual example.
Claire Kelly
It doesn’t always have to be, you know, someone who seems introverted becoming an extrovert because that’s not necessarily what we want either. You know, I have a lot of time for introverts and I think being able to stand on stage and perform is not necessarily what everyone needs to do, but I do think that it was a pretty great reminder of how confidence can propel students to new heights and give them the self-awareness that hey maybe I already had that in me. I had those those really nascent performing skills or I really wanted to show off my dancing and having my friends around me doing the same thing allowed me to do that or the environment was safe and it was low risk and I could do this. And maybe it took four years to get there, but it’s a memory that they’re going to have. And I think it’s also a skill that’s going to propel them forward. So that’s really what I saw. I think about a little talent show I had when I was in elementary school and I rapped a song by Eminem with two of my friends
Sam Demma
I think about a little talent show I had when I was in elementary school and I rapped a song by Eminem with two of my friends. It was absolutely terrible but I still think about it and I remember the feeling I had personally when I walked off stage and felt so proud that I did it Knowing that I was really nervous knowing that I was really Embarrassed even a little bit about the performance, but that I still showed up anyway. And I’m sure so many students built so much confidence as a result of that event. And if you’re listening right now, thinking about doing something similar, use this as a case study. I think it provides such a unique opportunity for students and staff to introspect and reflect being a part of the experience. Something you said earlier was that students throughout school are learning so much about themselves. And I believe that all humans are consistently learning things about themselves as they go through life. And one of the greatest teachers is our own mistakes, our own learnings. And I think about myself, you know, I just organized a cross candidate trip, and I was a pretty terrible manager of others. I tried with my limited skill set managing others, and it all went well from other people’s perspectives, including the people I managed, but I learned a lot. And there’s a lot of things I would do differently if I did something like that again. I’m curious, what are some of your learnings in education as an educator that other educators tuning in might be able to learn from your experiences?
Claire Kelly
Wow, well that’s a great question, Sam. And thank you. I like your little anecdote of bringing everyone across Canada. That’s really, that sounds like an amazing trip. That was cool. I guess in terms of mistakes, I’m sure I’ve made many and probably on a daily basis. So I’m pretty comfortable with most of them, I think. I think, you know, there are always an opportunity for learning. And as educators, you know, I think we go into education because we like learning, we were lifelong learners and there’s nothing like experience. So I think like personally, yes, of course, lots of mistakes professionally. I’d say that, you know, one that comes to mind for me is in the beginning of my career, I taught English and history. I still teach English, but not history. And I teach a little bit, not as much as I used to now that I’m in an assistant head role, but in the, yeah, at the very beginning, in the first few years, I talked far too much. I just, I thought, I don’t know what I thought. I, I, I, you know, too much lecturing, too much standing in front of the class or sitting in, sitting with the class and, um, you know, too much, uh, stage on the stage behavior. And what I think I, like, I think I know why. There’s a sense, certainly when you’re starting out, you want to show these kids who you’re not that separated from age or you don’t think you are, although I think they always think, oh, she’s so old. She is as old, even though I was probably 25. I think I wanted to show that I knew what I was doing and that I belonged there. I belonged I belong there with my own classroom. And I had knowledge and yeah, I’m sure that’s where it was coming from. But certainly in the last 20 years or so, I’ve been using the Harkness method as an English teacher, certainly at our school, and it’s really changed the way I teach English. And it’s one of our certainly foundational programs at the school that we’re very proud of, but it’s really changed the way I think I do a lot of things. Harkness, I don’t know if you’re familiar with it, it’s a very constructivist and democratic sort of way of teaching, where you’re all sitting around a table and I facilitate, so I set it up, I draw maps, I keep track of who said what, and I inject things here and there just to kind of prompt and see where the conversation will go. But ultimately, it’s not about me. It’s really all about the students and how they build on each other and what they’re able to share and debate and critique and extend and all that. And I think the best conversations really happen when I’ve set the stage, but when I just sit back and listen.
Sam Demma
What a powerful lesson in teaching. I drew some parallels immediately to speaking on stage and how powerful silence is for audience members because it gives them an opportunity to digest the information you’re sharing or answer the questions you’re asking and engage with the stories. And I think there’s a cool parallel there too. I was at Crofton House in Vancouver. They had a lot of classrooms with oval shaped tables and they’d have these really cool conversations where everyone feels engaged because you’re all looking at each other. There’s a formal name for it and I’m forgetting it, but maybe you know.
Claire Kelly
Yeah, it might be like the Harkness Method.
Sam Demma
Okay. Yeah. Yeah, so I appreciate you sharing that and I love the reflection of speaking less and allowing the students to be more involved with the content and with each other. What is something that keeps you hopeful, like keeps you motivated and keeps you showing up?
Claire Kelly
Yeah, that’s a great question. Another great question. So, like what gets me out of bed in the morning? I think you always have to have an answer for that, right? And it’s a good reminder, especially as you get further on in your career. I think for me, this is going to sound really Pollyanna-ish, but I love my life. I love what I do. I love that, as I mentioned earlier, like every day is different. So even though I’ve been at this school, I’ve worked at two big schools in my career, and I can honestly say like every day is different. I’ve never had the same job two years in a row. Not because I keep moving around in any way, but just the job is different. It’s so dynamic to work with students and to work with children and to have, you know, we must have 150-200 interactions a day. So, what, you know, there’s the plan and then there’s the reality of the up and down and the crossfire dialogue and and all the things that happen and it’s just a, you know, it’s really an incredible experience to work in a school if you like students and I think, you know, they just have so much to offer. I love working with teenagers. Yeah, you know, also I have a family that I love. I love my husband, my kids. One of my sons goes to our school as well. He just started, so that’s been really powerful for me to see my world through his eyes and to experience a little bit more. I feel like I get the full student experience through him. And he’s new this year. He’s, I guess if our school had used those terms, he would be a freshman. He’s brand new and he’s in the first year we offer. He’s in grade seven. So he’s learning all about the rhythms of the school day, but rhythms of the year, the programming, the teachers, the other students, what to expect, what he should be striving for, what he really likes himself. So it’s been really, really, really, yeah, it’s just an incredible education for me to see that through his eyes, and I’m really looking forward to this journey together, if you will.
Sam Demma
That’s awesome. You get to hear about the impact of the structure of the school and the opportunities and the programs in student life, right in front of your own eyes with your son, which is awesome.
Claire Kelly
Absolutely, and you know he tells me if I’m wrong too, which is also really important.
Sam Demma
That’s cool. I really appreciate you taking the time just to talk a little bit about your journey, some of your beliefs around education, some of the opportunities you believe that exist right now, some of the challenges. You’re doing a phenomenal job and there’s probably educators right now listening to this thinking to themselves, wow, this, Claire’s inspiring, you know, especially those that are just starting in the journey themselves. If there is an educator listening to this thinking that and they want to reach out and ask a question or just share some gratitude after hearing this interview, what would be the best way for them to get in touch?
Claire Kelly
Oh, thanks, Sam. Those are really kind words, first of all. And yeah, I love connecting with people. So I’m always happy to answer emails or, you know, be on social media. So probably through my email is the best way, ckelly@appleby.on.ca or through LinkedIn. Yeah, those are probably my go-to’s.
Sam Demma
Awesome. Claire, Dr. Kelly, thank you so much for coming on the show. It’s been a pleasure. Keep up the amazing work and I look forward to crossing paths again soon.
Claire Kelly
Thanks so much, Sam. It was a pleasure and really nice to see you again.
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