Episode 114: Supporting School Leaders with Cynthia Rapaido
Cynthia Rapaido is a highly accomplished educator with over 30 years of experience in K-12 education. She’s spent time as a high school principal, assistant principal and teacher, and went on to do work many roles in higher education. With so much experience built up over the years, she recently put the lessons she learned into her book, Step Up Your School Leadership Game.
In our discussion, Cynthia emphasizes the importance of mentorship and networking in education. She also breaks down the strategies she’s developed, such as the Fruit Leadership Chart to foster better understanding and collaboration among teachers.
Topics Discussed:
Cynthia’s transition from teacher to administrator
Why Cynthia wrote her new book, Step Up Your School Leadership Game
Advice for educators who are ready for something new
Resources mentioned:
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Read the transcript for this episode:
Welcome to Educator Forever, where we empower teachers to innovate education. Join us each week to hear stories of teachers expanding their impacts beyond the classroom and explore ways to reimagine teaching and learning.
Dr Cynthia Rapaido, a highly accomplished educator, holds an EDD in international and multicultural education, and an MA in educational administration, with over 30 years of experience in K 12 education, she has served as a high school principal, assistant principal and teacher, gaining a comprehensive understanding of the educational landscape across various schools and districts. Dr Repetto is dedication extends to higher education, where she has contributed significantly as a faculty, lecturer, dissertation advisor and university Field Supervisor. Her passion for teaching, mentoring and coaching educators is evident in her continuing role as an education leadership coach. In July 2024 Dr Repetto published her first book, step up your school leadership game, the new Administrator's Guide lessons to navigate big and small challenges with confidence and purpose. Welcome, Cynthia, so nice to have you here. Thanks, Lily.
Cynthia Rapaido
Nice to meet you and see you as well.
Lily Jones
So I'd love for you to start us off by walking us through your journey as an educator in any direction you want to take it. Okay?
Cynthia Rapaido
So in terms of going into education, I didn't think I was going to go into education. I was studying biology and as my undergrad, and I thought I was going to go into the medical field in some way, whether it's veterinary or I just didn't know what I was going to do medical field. And then I started hearing like physical therapy, occupational therapy things that I didn't know exactly, because I never had those done to myself. I never had to take no physical therapy as any kind of treatment. And then when I was in my last year of school and in college, people were asking, Okay, so some of them are going to med school, dental school. And I thought, well, I don't know what I'm going to do. And then one of my friends said he was going to go into teaching. And I thought, Oh, I never thought about that. And he was, he was actually in a different major, he was math, and I thought, I think I'm going to do that too. So then my mom and dad were like, you're going to go back to school. Yeah, I'm gonna do one more year, whatever. I don't remember how many years I was, one or two years. And then I became a science teacher, high school science teacher, biology and chemistry. And did that for nine years. And in those in those last few years, I thought, now, how am I going to move in that salary schedule? Because we know that teachers don't make and I'm doing all the all those additional duties, and I'm thinking, Gosh, I'm struggling during the summers, and what can I do? I'm doing part time jobs, making ends meet. And then I thought, Okay, well, I'll just go back and get my admin credential. And so I I did that, and one of the the requirements before we graduated was to write a resume and a letter for a job application. So I thought, Okay. And they go, Okay, now you have to send up. Thinking, okay, all right, sure. And so then I sent it, and then I had these job interviews for administration. They tricked you. What am I doing? And then I know that you're from the you also went to the Bay Area from the bay area of San Francisco. And so one of the positions was for Oakland Unified School District. And I thought, Oh, cool. Let me go to an interview for that. And then I had another interview in San Mateo. And I thought, hmm, but wait, I thought I wanted to just see what it was like. And then so somebody said, oh, so if you just do it, just do it for a couple of years, and then you'll decide if you like it. And I remember that first year, I thought, Oh, my God, what am I doing in administration? This is, this is like 90 degrees, uphill learning and no sleep, no rest. Everything was a learning curve. But that year one became year two. Year Two became year three. And 17 years later, I was still an assistant principal, and I thought, I'm gonna go back and get my doctorate, because there was this program that I went one of the professional development was on courageous conversations with Glenn Singleton, and yeah, that really moved me, because I thought, wow, we're really talking about race. And this is in, gosh, I don't remember what year it was, so in the early 2000s and I thought I want to do what he does. But what is that called? What kind of conference, what kind of what kind of workshop is, would this be? And so that's what I said. I'm going to go and look for a program in the education, you know, get my EDD. And I didn't even know what an EDD was. I just I'll get a doctor. I don't even know what I'm where I'm going with it. Everything was just kind of trial and error. And then I ended up going to us. Staff University of San Francisco, finding the EdD program in international and multicultural education, thinking, this is going to get me to what Glenn Singleton is doing, that work on race, and just being able to not there wasn't even ethnic studies yet, and thinking, Okay, how do I work with administrators? And I really want to teach administrators, because they can make the difference and trickle down to the classroom. Otherwise, it's the teacher that's developing it, as you know, and but not if everybody's not on board, then it's just one class that can make that change. So then I ended up getting that the doctorate, and thinking, Okay, now I'm ready to teach this at the university, thinking I could do it in the admin credential program or something like that. And one of the professors said, Cynthia, if you really want to work at the University, then you should become a principal. I thought, really, I don't want to be a principal. In my head, I was thinking, I don't want to be a principal. I mean the pay. I mean, even if you paid me $10,000 extra, I just thought, that's just a lot of work, a lot Yeah. And I just said, All right, I'll do because even if it's for three years or so, so then I got hired as a well, then there was like a path of to one of my other professors said, Cynthia, you don't have to do that. You can actually co teach with me at the university. I'll let you co teach with me in the Leadership Studies program, and you can see if you like it. And so I ended up doing that. I know it was really cool to be able to teach at the university and then still look at, okay, do I want to? I mean, I'm taking on this principalship position and just learning, learning. And then they the superintendent that hired me. I thought, Oh, great. I get to work with this great superintendent, great reputation. And then he said that he was leaving in a year. Oh, no, I came here because of you. And so I just said, I feel really sad that I'm here. I'm here to serve the students and staff and faculty. I committed because I said I would be here for three years, and I told you I would do that, but you also knew that I was thinking going to the university and after year three, and he said, You don't have to follow that, because that was a communication between me and you, and if you choose not to stick around, you know, for year two or year three, that's there's no commitment. And I thought, okay, that kind of gave me that freedom to just say, Okay, I'm out of this. But then I just said, but I I committed to this. I'm all all and I jumped in and dove in, and I just said, Okay, I'm sticking with this. And so I stayed there for five years.
Lily Jones
Oh, above three. Yeah, what did you how'd you like it? What did you think about being a principal?
Cynthia Rapaido
It was really amazing, way different than, I mean, there's a lot of responsibilities. Some of it is political, but at the same time, a lot of it's just, you know, building those relationships with the faculty staff and just kind of being inclusive and setting the climate. It was, it was fun. And I would get like this, little like, hi, just kind of Oh, I get to know do this, and I can be authentic and not have to follow my as my principal, as the assistant principal, because I have to always kind of follow the lead. Then I was kind of, I felt really good about that. It's kind of like being you're a teacher, and you're a teacher of your own classroom. You're you can set the tone, you can build those relationships, make things count. So that was that. And then in 2019 that was the year five. Then my dad was having struggles with his health, so I had to retire. Well, I retired early to help take care of them.
Lily Jones
Mm, hmm, exactly. You were able to do that.
Cynthia Rapaido
Yeah, yeah, to be able to spend time with with him. And then also, and then he passed, and then my mom, taking care of my mom. And then she passed. And then, but I just said, Okay, well, during this time, I need something to to keep me, keep my foot in the door, right. And so then I ended up finding work at UC Berkeley, in their teacher ed program, and then I also worked at Cal State, East Bay, in their teacher ed program. And just being able to, it's like a full circle of now I'm working with these I think you remember what it's like to be in the having a supervisor from the university. Diversity, yes, absolutely, yeah. So that's me, and then I get to do the administrators too, and then I wrote a book, and so that and facilitating workshops and just having fun with it. So that's my new my new reinvention of myself.
Lily Jones
I love that. And I love throughout your story, you know, this openness to try new things. You know, whether it was the same direction you wanted to go in or somebody giving you advice, it seems like you really were able to make the most out of so many different situations and kind of navigate that of feeling of what you want to do, you know, versus, like, the unknown always kind of this mix that we're all navigating of like, okay, this is what I think I want to do next. Like, let me try it on, and let me be open to feedback, and let me just learn through doing it.
Cynthia Rapaido
Right. Yeah, and not even knowing where it's going to lead to, but just just learning,
Lily Jones
Yes, absolutely. And I love now that you're helping newer teachers and administrators. I had a few years when I left the classroom also being a student teaching supervisor, and I loved it, being able to go into all these classrooms and help beginning teachers and kind of think back into what was helpful for me as a beginning teacher. It was just such a time of growth for me personally, you know, being able to do that. So I'd love to hear a little bit more about that. Like, what do you like about supervising teachers or administrators? How is that for you?
Cynthia Rapaido
It's really pretty cool. I think, you know, there's a lot of unknown of what to do. I think the student teacher teachers are lucky that they get a mentor to kind of follow, but then it's also if the mentor is good that makes a big difference, because there can be mentors that can be one way or the highway, and there's others that will really mentor and help them the student teachers. And then you have those that are interns that took on the position to get paid, that don't have a mentor, and they are the ones that probably need the most support in terms of classroom management, materials, resources, on a network with a colleague when there's no time to network. So being able to work with them one on one, and kind of not just one on one, but I used to say, I'm going to have a cohort. I'm going to have this cohort. We're going to meet, you know, five times in first semester, five times second semester, so I can help keep us all on the same page, and at least you guys get to network yourselves. I think that was really, or is also really important for them for their growth. And the second thing with my administrators, same thing.
Lily Jones
Yeah. Having that community, you know, of other teachers or other educators, is super key. And also, like you're saying, so hard to come by when you're a busy teacher or a busy administrator, like, how do you create that for yourself?
Cynthia Rapaido
Yeah, it's really hard. And I think even for administrators, it's not easy once they become once they become an administrator, what resources do they have, except for whoever their boss is? Let's say if you're a system principal, then is your mentor going to be your principal? Or can you or can Is it easy to find other mentors that will support support you?
Lily Jones
Yeah, absolutely. And so I know that you also recently wrote a book which congratulations.
Cynthia Rapaido
Thank you.
Lily Jones
Tell us about the book.
Cynthia Rapaido
Sure it is about it's called Step up your school leadership game. It looks like this, I'll show it to you. Let's see it. Yeah, thank you. So step up your school leadership game, and it's the new Administrators Guide, and it's for lessons to navigate big and small challenges with confidence and purpose. So yeah, what made me want to write it was it's actually like what I would have wanted, because once I started becoming an administrator, it was hard. I'm sure it was really hard, and then to become a principal, kind of, okay, I watched three administrators, three of my principals, and each of them were very different, but really, all of them were really outstanding, and I learned from them, and I watched them. But of course, that was when I thought, I don't want to be a principal, but I'm still watching what they do and their demands of what they expect of me. And I thought, okay, when I'm ready, or when that happened, it's like, okay, I put the pieces all together, and this is what I knew that I didn't know, and what I needed to know, and all the Miss. Takes that are in the book, some of the mistakes, most of the mistakes that I made.
Lily Jones
That's how we learn. Fantastic. And I love the idea of writing a book that you wish you had. I often feel like that with my work at educator forever, like creating programs or creating a community that I wish I had. You know, it's so good, oh no, until we don't have something, and then it's like, all right, this is really one. What I wish I had. Can be such a great place to start?
Cynthia Rapaido
Yeah, I think that's great what you're doing. Thank you.
Lily Jones
Yeah. I mean, definitely it was an unknown territory when I was like, Okay, I want to work in education. I want to have more flexibility. What can I do? And bound through, stumbling my way through and meeting people. And so, yeah, I want to make it easier for other people, for sure.
Cynthia Rapaido
Yeah, I think that's great. And then in terms of, like, the curriculum and, you know, developing that everybody needs help. So I think that is so giving of a view to have that kind of space. I think that's so important.
Lily Jones
Hey, yeah, I mean, it's like, can't not be a teacher.
Cynthia Rapaido
Right?
Lily Jones
Oh, I could create a class about this
Cynthia Rapaido
Exactly. Yeah, you're mentioning those that don't know what to do. It's wonderful.
Lily Jones
So I know you have some great tools, and I'd love for you to talk us through some of them. The first one is the fruit leadership chart. Can you tell us about that?
Cynthia Rapaido
Absolutely. So in my book, it's just a small section and it so I'll do it with you, if you're okay. So there's four different fruits, and you just tell me what resonates with you? Okay, apple, orange, pineapple and grapes. I think I go with Grapes, grapes. Okay, so when you think of, when you think about the different fruits and an apple. When you think of an apple, it's super easy to to work with. All you do is you wash it, and then you bite into it, right? And then, when you think of grapes, they're all of them are on this little branch, and you pick at them. But they're all connected. Pineapples, they have this big old crown, and then there's eyes on the outside. And there's this flesh on the inside, of course, but the eyes on the outside, it's kind of unique in its own way, right? And then we have an orange that when you can't even get to it until you peel it open. And then everything is all organized, and even the pulp is all organized. And there's skin around skin, very detailed. So when you think about all those different characteristics, and Apple is basically the action. So they implement, well, they initiate and implement, execute done. They just want to get the task done, rapes or people persons. So they like to connect with other people. They like that harmonious relationship. They like to like, build consensus, a community. And then we have the pineapple with their big ideas. That's what they have, big ideas, a lot of visionary a lot of imagination. What are the possibilities? Open ended, and then you have the oranges that are again, detailed oriented, meticulous, very mindful of every detail. No. Now when I ask you again, what kind of fruit resonates with you based on those characteristics. What do you think you are?
Lily Jones
Oh, good question. I mean, I do think I'm probably a grape or a bunch of grapes. I do appreciate the building of community and coming to consensus and having the harmonious relationship. I also do resonate with the pineapple too. Though that's good.
Cynthia Rapaido
That's really good. So part of it is now that you know those those other fruits, is to develop those other fruit skills. So that way you're not only isolating yourself with being a grape and the group consensus. And if you are grape pineapple, then you had the big idea. And now working with the action stamp is trying to initiate those, those thoughts, and then working on those little details of everything. And then when you work with other people, you can find out who, what are they? And then you go, Oh, okay, so I know that you're one as an apple. I know they're going to want to be all action oriented, but this is what I need if I'm a great, because I'm kind of a great too. If I'm a grape, I need for you to slow down and check in with me, right? I need for you to check in with me. I'm a great. That's what I need. So if I could communicate that to the apple. Or to the orange. The oranges tend to not always be so sensitive. They're just matter of fact. Here are the facts. Here are the data. Here's, you know, I'm going to be honest here. This is what we have. And so being able to say, Hey, this is how I am. I'm sensitive, and I need you to be inclusive. And then if I find out, okay, and you're an apple, I know I need to kind of switch my my role, and kind of jump on the wagon quick with that person to get stuff done, right? So those are the things where, again, if you're working with a pineapple, kind of like, allow them to enjoy and give, give ideas, but then at the same time, helping them be delivered, be deliberate with their plans, because they can think and think and think and think, but then nothing comes into fruition.
Lily Jones
Sure, they need an orange.
Cynthia Rapaido
That's that's the fruit leadership style.
Lily Jones
Yeah, that's great. I think that having the tool to talk about it and to compare with other people is just really interesting. You know, like having the vocabulary and starting the conversation and being able to compare and be able to think about how these different fruits or these different people work together is really helpful.
Cynthia Rapaido
Yeah, it is.
Lily Jones
Yeah. So I know another tool or an activity that you have is your multifaceted identity. Can you jump through that?
Cynthia Rapaido
Sure. So the multifaceted identity is basically all the different things that make up who you are, in terms of what you value, or just your identity. So let's say it can be religion. It can be ethnicity, race, education, social status, my background. So if I were to talk about myself, they would give you an understanding of who I am as a person and how we can relate to each other. And then doing it with other people, it kind of opens up a dialog and understanding of the journey that we did. So I can talk about myself really quickly. I can say I'm a Navy brat. My guy was in the Navy, and so people ask, Where are you from? I don't know what to say. I can say I'm from a lot of different places. I grew up in Connecticut. I grew up in the Philippines. I grew up from, you know, San Diego, Cal, you know, different parts of California and but I'm Filipino, and my parents are from the Philippines, so I'm second generation. I have, you know, five siblings. I'm number four. So I think it kind of shows a little bit of more about who I am and what I value, and I could talk about, you know, my schooling, my education. So being a navy brat, I went to six different elementary schools. So of course, there's going to be broken gaps in between, but I think it would give somebody an understanding of my my lived experiences.
Lily Jones
Absolutely. And connections too, of like, you know, even as you talk, it's like, oh, like, you know, I have two siblings. Or my dad also grew up, growing going around to many different states, and lived in like, 12 states before he was 13. You know, having those connections with people, and even when stories are very different, being able to find some common ground too.
Cynthia Rapaido
Right. And then even, like, okay, we're both women females, and we can talk, definitely talk about our own experiences in education and growing up. I mean that that is another thing. Is gender and, yeah, it's just connecting.
Lily Jones
Yes, absolutely. And we're all multifaceted. Rather than just being like we are women, you know, like we are many things, all of us. And so being able to have those conversations.
Cynthia Rapaido
Right. And you can be about hobbies. I mean, you can be okay. What do you like to do Lily, and maybe we have some similarities in that sense of just building that is again creating that community and the network opportunities to share out.
Lily Jones
And do you imagine, is this activity usually done with teachers? Like, would this be something an administrator does with teachers, or teachers do with students, or both?
Cynthia Rapaido
Yeah, both. Yeah, absolutely.
Lily Jones
I mean, I think that's so interesting too, just thinking about, you know, I've moved into teaching teachers, and so it's like, I used to teach kindergarten, but it's pretty much the same thing, right? Like, it's like I do the same things and use the same skills in a lot of ways. So I love this idea, too, of an activity that you can do with many different age students or grown ups, and that is helpful for everyone.
Cynthia Rapaido
Oh, yeah, especially if you're with you know, adults. That's one thing. But you can talk to the kids and have them kind of they might not know the differences, but they can talk about, oh, what do you what do you like to do? What's your favorite color, and why is it if, I mean, I'm sure that that might be something that you've done in your classes, or what is your favorite book, and yeah, it can be anything that's your favorite, and then put that in your the conversation, and then it just builds, builds, not just the networking, but a little understanding of each other.
Lily Jones
Absolutely. Yeah, those true community I think.
Cynthia Rapaido
Yeah, whatever that favorite is, whether it's your favorite movie, your favorite coffee, whatever it is, what's your favorite part of that movie or, I mean, it just keep, keep going on from there.
Lily Jones
Absolutely So thinking back over your career and the many amazing things that you've done, I'm curious what you've learned about yourself, through your work as an educator?
Cynthia Rapaido
What I've learned about myself, I know I what I love is the coaching, the helping others, the the teaching of it, not so much the grading.
Lily Jones
No..
Cynthia Rapaido
I definitely like the teaching. So whether it's teaching how to how to it's not even this. It could be the subject, but it can be how to do something, how to make jewelry, how to, you know, cook something. I don't know, that's always kind of fun. So in terms of myself, it's that giving piece, and I like that, the building of that community, that networking. So as I've gotten older, in my age and learning about myself, it's kind of like, I like, I like people. I want to I want people to connect. I want people to share their stories, because that's where we learn from each other we don't. I mean, we can learn from books, but it's that personalized relationship that make a big difference.
Lily Jones
Yeah, that's lovely. So thinking about educators who may be at a crossroads, you know, maybe kind of similar to when you were thinking about becoming an administrator or going back to school or trying work beyond the classroom. What advice would you have for them?
Cynthia Rapaido
For which ones?
Lily Jones
Any of the educators who are at a crossroads? I would say.
Cynthia Rapaido
Okay, I would say, definitely, network. I think that's really key. Network, volunteer, reach out, try new things. Don't be afraid to tap other people for to be a mentor, ask, I mean, all they have to do is just say, hey, you know I like that career that you're in. How did you get there? And what does it take? And would you like to be my mentor? Could you be my unofficial mentor? Even just to ask that, if they say, No, that's okay, right? It's okay to get a no, but if you know that they are in that position that you want to be in, then don't be afraid to ask for them to coach you along. I wish I did that early in my career, because I didn't know. And yeah, now that I know some of the things that would be my advice,
Lily Jones
That's great advice. And I think asking is so powerful. Yeah, well, sometimes it just takes asking and asking for the connection or asking for a conversation. You know, it doesn't have to be a gigantic ask, but just taking that first step, right?
Cynthia Rapaido
And don't be afraid to even just try things. I mean, I didn't think I mean, I didn't think I was going to write a book. I just said, Okay, I'm going to write a book. And, okay, I'm going to do this and just, just do it. Don't be afraid. Yeah, I think people are afraid of just, you know, changing, changing careers. I think people has hesitate, yeah, yeah, absolutely.
Lily Jones
And it's scary. And I think, you know, trying something new is scary, but it's also so interesting, fine. So I love the advice of just start. You know, it doesn't have to be like you're stopping everything, and, you know, writing your book 100% of the time, but it could be that you're writing your book a little bit every weekend, you know, taking that step of feeling it out, and maybe you decide you love it, and maybe you decide you don't, but we don't know until we really try it.
Cynthia Rapaido
Right. And then just join organizations, see if you like them. Join clubs. I mean, it's kind of like going back into high school. Kind of just join things and see if you like it. You don't have to commit to anything. I mean you, I think you need to research what your interests are, and then you decide, okay, I think I'm going to commit to that.
Lily Jones
Yeah, yeah, definitely, and try it out, like give yourself a chance to try. I think that's wonderful advice. Yeah, absolutely. Cynthia, it's been so nice talking with you. Can you tell folks how they can connect with you?
Cynthia Rapaido
Oh, Lily, it's so nice to talk with you. People can reach me through LinkedIn, and that's my main connection. It's Cynthia rapido. And they can also email me through Cynthia rapido at Gmail, if they want to try to do that as well. Wonderful.
Lily Jones
We'll put those links in the show notes as well. Thank you so much.
Cynthia Rapaido
Thanks, Lily, nice to meet you. You too. Okay, take care.
Lily Jones
You too. Bye, bye.
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