April 28, 2025
Episode 28: Navigating School Leadership: Identity, Culture, and Lessons from Dr. Cynthia Rapaido
Fan Mail! From reluctant administrator to award-winning principal, Dr. Cynthia Rapaido's remarkable 30-year journey through educational leadership offers powerful insights for anyone considering school administration. What began as an academic exercise to move up the salary scale unexpectedly blossomed into a 22-year administrative career spanning assistant principalship, principalship, and higher education mentoring. Dr. Rapaido's story uniquely illuminates the intersection of cultural iden...
From reluctant administrator to award-winning principal, Dr. Cynthia Rapaido's remarkable 30-year journey through educational leadership offers powerful insights for anyone considering school administration. What began as an academic exercise to move up the salary scale unexpectedly blossomed into a 22-year administrative career spanning assistant principalship, principalship, and higher education mentoring.
Dr. Rapaido's story uniquely illuminates the intersection of cultural identity and educational leadership. As a Filipino woman navigating leadership roles traditionally dominated by different voices, she learned to balance her cultural values emphasizing harmony with the directness required for effective administration. Her powerful account of finding her voice—learning that "we can agree to disagree"—serves as an inspiring example for leaders from all backgrounds struggling to reconcile personal identity with professional expectations.
The conversation delves deep into the foundation of effective school leadership: knowing yourself. Dr. Rapaido describes the "fruit leadership style chart" from her book "Step Up Your School Leadership Game," which helps administrators identify their natural strengths and approaches. She emphasizes the critical importance of understanding your core values and non-negotiables before stepping into leadership positions, ensuring alignment between personal philosophy and school or district culture.
For current administrators struggling with work-life balance, Dr. Rapaido offers practical wisdom about scheduling "big rocks"—the activities that provide restoration and reflection—and being fully present during those times. Her approach to leadership development extends beyond technique to encompass holistic well-being, something often overlooked in leadership training.
Whether you're a teacher considering administration, a new principal seeking guidance, or an experienced leader looking to mentor others, this episode provides both practical strategies and philosophical depth. Connect with Dr. Rapaido through LinkedIn or email (crapaido@gmail.com) to learn more about her leadership development work and how you might benefit from her experiences as you build your own educational leadership identity. What leadership fruit are you?
Connect with Dr. Cynthia Rapaido:
email: crapaido@gmail.com
Book: " Step Up Your School Leadership Game "
Connect with Principal JL Click Here:
Want to be a guest on Educational Leadership with Principal JL?
Send Principal JL a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/1742787866678447e5bdb89c1
00:00 - Introduction to Dr. Cynthia Rapaido
03:17 - Journey from Biology to Education
07:39 - Transition to Educational Leadership
11:58 - Principal Role and Higher Education
18:56 - Cultural Identity in Leadership
25:02 - Writing "Step Up Your Leadership Game"
30:06 - Balancing Work and Personal Life
49:07 - Advice for Aspiring Leaders
52:59 - Closing Thoughts and Contact Information
WEBVTT
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Today I am thrilled to welcome Dr Cynthia Rapaido to the podcast.
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She is a longtime educator and leader with over 30 years of experience in California schools, serving as a teacher, assistant, principal, principal and higher education mentor.
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She holds an educational doctorate in international and multicultural education and recently published her first book called Step Up your School Leadership Game a guide for new administrators.
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An award-winning leader and passionate advocate for equity and inclusion, Dr Rapaido continues to coach and inspire educators across all levels.
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Now here is our conversation.
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Welcome back, everybody for another episode of the Educational Leadership Podcast.
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Today I have a special guest, Dr Cynthia Rapaido.
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Cynthia, welcome to the show.
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Thank you.
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Thank you for having me, Jeff.
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All right, I like to start off asking every guest the same question what inspired you to pursue a career in education.
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It's funny that you asked that question, because when I was in college I didn't even think about going into education at all.
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I was a biology major, thinking I was going to go into the medical field and I was even doing.
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I was a candy striper, I was working in the surgical office, a surgical room, and just trying to navigate my way around the hospital in terms of careers just trying to navigate my way around the hospital in terms of careers.
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But there was this opening at San Diego State where they were looking for peer advisors, which were college students going on to the high school campuses and trying to help the high school students apply for colleges.
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And I thought, oh well, that's me, because I didn't know much about getting into college, I kind of fell through the cracks.
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So I didn't know I had to take the SAT, I didn't know that I had to have a certain GPA, certain courses, and then by doing that that got me into coaching or mentoring high school kids and so I loved that.
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And then I just totally went the opposite direction.
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I said, okay, I'm getting a biology degree and I'm going to teach high school biology.
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So that was my route and didn't go the medical field way my route and didn't go the medical field way.
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Well, that's really interesting.
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The more I do this podcast, the more I learned that a lot of people that get into education may not be thinking about education as a first career choice.
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And that was kind of like my journey as well, Like I thought I was going to go become a physical therapist but it wasn't until I got into coaching and I decided you know what I really like this teaching gig and the education side, so that really inspired me to get into education.
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So it's really fun to hear how people get into education and pursue their careers.
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So let's share a little bit about your early years in the classroom.
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What subjects or grades did you teach and what did you love most about teaching?
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I was a biology teacher biology, life science and when I got hired, my first year it was biology, chemistry, human anatomy.
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Second year, chemistry.
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There was one more.
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So all of the classes were different.
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So I had five different prep periods.
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I didn't know, I couldn't keep up with all of the different classes in terms of, okay, which one am I going to do the lesson plan first, but I didn't have anything to compare it to Knowing.
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Now it's like, okay, I should have just taken one that had just two classes that I can really focus on.
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But what did I love about that?
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I loved connecting with the kids and I love the kids.
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They were high school kids, ninth graders to seniors.
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The seniors were, you know, the ones that were smart and were already thinking about college.
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And then you had the ones that were smart and were already thinking about college, and then you had the squirrely little ninth graders that I really loved connecting with the life science ones.
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Oh, one of them was like the EL life science.
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So, just being able to connect with the kids and turning them on to science, I just wanted to make sure that they loved science and I didn't want them to, you know, not like science.
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After they took me as a teacher.
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So I said if they're going to take life science, they're going to want to go on to biology.
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If they take biology, they're going to want to take chemistry.
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So that was my goal was for them to fall in love with science.
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You bet I mean that's great.
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I was a math teacher and you know how people love math, but you know, I think that was part of my goal as a teacher as well, where I was like you know what.
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You may not love the subject that I teach, but my goal is to help you at least like it, or at least you know, develop appreciation of the work.
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The work and so it sounds like you you had that same type of experience as well as a science teacher is to help kids really love it and fall in love with that, that same subject area that you're passionate about and what I've learned.
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You know, if you're passionate about something, the kids will be passionate about it as well.
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You know, you kind of talked about your, you know your teaching here a little bit, but let's really get to.
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What we really want to know about is what got you to think about becoming a school leader, what motivated you to transition from teacher into administration?
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Good question.
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I was in my seventh year of teaching.
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I was in my seventh year of teaching, there was that salary schedule and knowing that I had to, I wasn't going to move very far along in terms of the payroll.
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So I thought I'm going to take some more classes just to go up in the scale and just said, well, I think I'm going to get my master's and I'll get a credential in administrative services.
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And so I took the classes and one of the requirements for the last, the very last class was come up with a resume, come up with your cover letter and apply.
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I thought, okay, I'll just write my cover letter and apply as an assignment, because I already got a.
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You know, I got an A on my resume.
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I thought, oh good, okay, so let's see what happens.
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And I got interviewed and I thought now what do I do?
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Do I really want to do that or do I want to go into?
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No, what do I want?
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To stay in teaching?
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Um, and so I talked with my principal and he said Cynthia, you've been doing stuff that's leadership role, you're doing after-school program.
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He said, cynthia, you've been doing stuff that's leadership role You're doing after school program.
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You know, you're club advisor.
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You've been working with the district office.
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That's because I like these things.
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But I don't know what.
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I don't know.
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And he said well, you're going to, we're going to give you a walkie talkie and we're going to let you sub for a little bit while somebody else is gone and see what happens.
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You know if you like it or not.
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And so he gave me that opportunity to do that.
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I thought it was just kind of awkward to be at my own school site and seeing my kids, and now they see me with the walkie talkie.
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And here I am.
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I told the kids.
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I said, if you get in trouble and you get sent to the office, you are going to do double time with me.
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I'm going to give you double suspension or whatever.
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It was class time, because I'm telling you now that I'm going to be out there, as you know, doing administration work.
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And they laughed, of course, the kids, you know they were behaving, but that's what got me into educational leadership as an AP.
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So I got the job, took the job and and I didn't think I was going to enjoy it Um did it for one year and I thought I'm not going to survive this first year.
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Um, this is crazy, but who do people doing this?
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And so year one became year two, and that year two became year 17.
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17.
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And then I went into principalship and did another five years.
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All right, let's talk about your assistant principalship a little bit.
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With that role, what are some key lessons or moments that you really shaped your leadership style?
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What really shaped you as a leader, as an AP, before you got into that principalship?
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When I was an AP, I thought that was all I wanted to be.
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I didn't have, I wasn't interested in going up the ladder and becoming a principal.
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But then when I was talking with the kids, they would introduce me to their mom or I would see them at the game and then they would say, oh, you're the principal, and I would say, no, I'm your assistant principal.
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And thinking, okay, if they think I'm their principal, then I'm going to pretend I'm the principal and I would walk around the campus and go hi, I would think of what does my principal do?
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No, she's out there, visible in front of everybody, stands in the hallway and thinking, okay, what do I need to do to make myself visible to not just the students but now the faculty?
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Because I needed to be a leader in that, and so finding a mentor to help me learn the other areas that weren't my strengths really helped me.
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After being an AP for 17 years, you stepped into the principalship role.
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What was that?
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Like you know, going from AP to a principalship, because they're kind of you know they're the same but yet there's two different worlds there.
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How was that transition?
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What are some big takeaways?
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You could talk about being that principal of the building and having the weight of that position on you where maybe you didn't have that as an AP at times.
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I think you know the big difference between that is you know, as an AP, you're second in command and so you, you humbly, you know, follow the lead and you follow and align everything with your leader, whether it's you know, your principal and the district office.
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But then becoming the principal is being able to identify who I am as a leader is really important.
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And then what are my goals and visions for the school and how do I align that with the district office and how do I lead everybody?
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It's not just a team, not just a department, but now it's everybody.
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It's not just a team, not just a department, but now it's everybody.
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And, as you had mentioned in some of your podcasts, it's like building those relationships with the cafeteria person or the students, the paraprofessionals, and making them visible, because it's the whole school.
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Yeah, you bet.
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So really that principal role I agree with that is where you really how do you get everybody to row the boat in the same direction, how do you get everybody to collaborate, work together?
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And that really comes from the top to where.
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If you have that value and you believe in that, that's going to transpire down all the way into your students.
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So people don't realize, and even studies and research has shown that that principalship is really key to helping your teachers learn and grow.
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But everybody learn and grow, not just your teachers, but your staff, your paraprofessionals, your custodians, everybody all the way down to the students.
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And so that's kind of the role that principalship really has.
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But let's talk about next transitioning from being a principal and you got into higher education.
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What was the reasoning for that?
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What prompted you to go?
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Hey, you know I really love what I'm doing, but you know what I want to take this next step into higher education, educational coaching.
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You know, does something.
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Was that something you planned or was that something that kind of just naturally happened for you?
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It wasn't planned and it wasn't natural.
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I had gone through some PD that the district wanted us to do.
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One of the PDs was on Courageous Conversations with Glenn Singleton and I thought that was so powerful and I thought how did he do that?
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How is he able to speak in front of administrators and talk about race?
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Because when I sat in the room I'm thinking, okay, I'm a female and I'm a person of color, but there was a lot of other people that were white and for him to have those conversations and kind of make us realize our race, our ethnicity, I thought I want to go back, I want to figure out what, how he did that, what did he study to be in that position?
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And I couldn't find a degree in that.
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But I then I looked at USF and USF, the University of San Francisco.
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They had a multicultural, international and multicultural education program and that's when I thought I want to study that, because now I'm going to see things internationally and multiculturally and just being more sensitive.
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And then that's where I thought I'm going to study that.
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And then I want to teach that at the university and I want to be with the administrators so I could teach them.
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So that way it becomes part of the admin credential program and then they can go back to their school and lead.
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So that was where I was thinking of that kind of picture.
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Yeah.
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So it sounds kind of like you saw something there was a need for and you're like you know what.
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That'd be really great if I can help that process, because I see this person really putting themselves out there and talking about these things that are very important.
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And how can I help?
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You know, lead the charge in that way, and so that's really great and powerful that you know you were able to recognize that, but then not just recognize it but actually go and do it Right.
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Yeah, yeah.
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So that's so.
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Was that part of your dissertation, your doctoral work?
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When you were going back and doing that?
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It became so.
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My doctoral work was titled Filipino American Educational Leaders in Northern California K-12 Public Schools Challenges and Opportunities, because it became the awareness of where are people that look like me?
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I am not seeing anybody that's Filipino.
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I might see some Asians you know the bigger race group but where are the Filipinos?
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And trying to find them as participants in my study, I only had like six participants.
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I couldn't find them, and so that became a huge passion of mine, and then it became an awareness of the learning of it all.
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You bet.
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So you know through that you have been a lecturer, you have been a dissertation chair through your time working in the university, as well as a university supervisor.
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Now tell me if I'm right on these.
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So the University of California, berkeley, the University of San Francisco, the California State University of East Bay is that correct on that one?
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Yes, did I get that one?
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Okay.
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So so, through these experiences, how were these experiences in higher education complement your work in K-12?
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How did you know doing that work complement that work that you previously did?
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So now, as a university supervisor, I'm working with teachers that are just entering the profession, trying to get their credentials, so it's inspiring them at the same time guiding them in terms of all the credential requirements to meet so that way they can get hired.
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So of course, we want good educators.
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And how can I help?
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It's all about how can I give, what can I give?
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How can I help you know beginning teachers or people going to you know into teaching?
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How can I help administrators aspire, help people aspire to different positions in education?
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So that was really huge for me.
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And so, in terms of all those different roles dissertation advisor, somebody had found me and said, hey, I'm doing something on Filipino Americans and I don't have any Filipino Americans where I live and they were like in Wisconsin, I think, and I felt great, this is a platform that I'm familiar with.
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I will be your dissertation advisor.
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So empowering her to do her dissertation and help her navigate the doctoral program, that was a lot of fun.
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But at the university level, all those different positions, it all goes back to serving in that servant leadership role and just helping the pipeline of educators, Because not only do we need teachers, we need educational leaders.
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You bet, you bet, and that's kind of the overall purpose of this podcast is to try to inspire that next generation of educational leaders and kind of give them the ins and outs of what it's like to be an educational leader, because there's not a lot out there for us and so, if anything that we can do to inspire the next generation because guess what, education doesn't go away we're going to have generations of education all the way down.
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I know we're kind of in that moment of time where it's, you know, being in education may not be the most glamorous job, but it's a very needed job and not a lot of people are getting into it for a lot of different reasons.
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I won't get into them, but it just comes down to it's becoming, like on my side, becoming harder and harder to get people to, you know, apply and for openings and like right now I have an opening and I only have a couple of candidates and it's kind of like, oh man, you used to have like 20 for this, you know, and now it's kind of just whittled down.
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But then that's where you got to get creative on how you hire and how you grow your own so you can have a workforce to come back.
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So it sounds like you're kind of developing and growing that workforce for education in those roles.
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So let's talk about your book.
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Step Up your School Leadership Game.
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You know what led you to write the book.
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Was there a defining moment?
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What made you feel compelled to write this book?
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I felt, you know, that I needed a book when I, when I went into education not just education, but as a assistant principal there were so many things that I didn't know that I wish I would have known.
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And trying to find books for beginners or or aspiring people.
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That's what inspired me to write the book.
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It's a mentor, it's a $25 mentor, for the rest of your life.
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You can pull it out of the shelf and go what do I need to do?
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Or what was that advice that was given?
00:20:29.883 --> 00:20:45.912
That's what inspired me, because I know that not everybody goes back to school per se to get a doctorate or get their master's, or they might not know the duties of an administrator.
00:20:45.912 --> 00:20:54.589
Sometimes, from a teacher's perspective, they want to separate themselves and they say, oh, you went to the dark side, but it's really not the dark side.
00:20:54.589 --> 00:20:57.324
It's like we're all in this together.
00:20:57.324 --> 00:20:59.761
There is no dark side.
00:20:59.761 --> 00:21:08.701
And to break that mindset of that and to say we're here together, whether you're the custodian, we're here.
00:21:08.701 --> 00:21:10.560
We're here to support you.
00:21:10.560 --> 00:21:14.099
That's what that book is about.
00:21:14.220 --> 00:21:36.215
Is for teachers, teachers, for administrators, for people who don't know what they do, what we do it's it's for them you know, it's really awesome that you have this book for those aspiring administrator even for the current administrators that may are, you know, curious, can they do something better or to get better at something.
00:21:36.215 --> 00:21:41.287
So it's really great that you have something out there for people to have.
00:21:41.287 --> 00:21:52.467
So you know, with that book, what do you think is some of the biggest takeaway that you would want a new or aspiring administrator to have you know from that book when they read it?
00:21:53.075 --> 00:21:58.419
I think it's like the first section is probably the key, which is know yourself.
00:21:58.419 --> 00:22:00.405
Know yourself as a leader.
00:22:00.405 --> 00:22:02.973
There's activities.
00:22:02.973 --> 00:22:10.765
I came up with a fruit leadership style chart where you can identify your strengths as a leader.
00:22:10.765 --> 00:22:15.044
And then there's also the multifaceted identity who are you as a leader, who are you working with?
00:22:15.044 --> 00:22:16.588
And then there's also the multifaceted identity who are you as a leader, who are you working with?
00:22:16.588 --> 00:22:22.296
And then building that emotional intelligence with all the different people you work with.
00:22:22.296 --> 00:22:30.390
And then knowing your core values, your non-negotiables and the goals for the school.
00:22:30.390 --> 00:22:32.438
So that's that first section.
00:22:32.438 --> 00:22:40.049
Wherever you go, at least if you know how you are, and then you can kind of assess okay, what's Jeff like?
00:22:40.049 --> 00:22:42.021
What fruit style is he?
00:22:42.021 --> 00:22:50.827
And then I would be able to work better with you based on what you describe as your fruit leadership style or your multifaceted identity.
00:22:50.827 --> 00:22:52.269
You bet.
00:22:52.355 --> 00:22:59.519
Yeah, that's really powerful for people to know is kind of know what their style is, who they are, what do they value.
00:22:59.519 --> 00:23:03.982
Because, just like people, districts are different.
00:23:03.982 --> 00:23:09.486
They have different alignments, they have different values, they have different expectations.
00:23:09.486 --> 00:23:19.472
And you got to make sure, yeah, you may want to go into becoming an administrator or principal, but you have to make sure that district you aligned with that district.
00:23:19.472 --> 00:23:37.134
Because if you get into a district you're not aligned with, you won't enjoy it, it's not going to be a good time for you because you're not going to have the same values and you're not going to have the same goals that you would if you knew who you were and you knew how to align yourself to that district.
00:23:37.295 --> 00:23:46.227
And I think that's really important for people to really understand that piece, because you can go become a principal somewhere, but make sure it's the right fit.
00:23:46.227 --> 00:23:54.262
And when you get into that and you do these interviews, you just know like, yeah, these things check off, these things work well.
00:23:54.262 --> 00:24:08.826
I know I'm going to be successful here because of what my values are aligned with theirs and we're going to be able to work together and to create that school environment that you really want to achieve with that.
00:24:08.826 --> 00:24:16.127
So that's what I hear you say on that, and I think that's really powerful for people to know when it comes down to that.
00:24:16.127 --> 00:24:17.958
I love how you said that too.
00:24:17.978 --> 00:24:27.166
Jeff, it's so important to know what the district wants and if our values are aligned, and that is really important.
00:24:27.996 --> 00:24:38.181
I know for me and my journey, when I did some interviewing and stuff like that, if I got into a district and we weren't aligned to it even if they would offer me the job I knew I was saying no.
00:24:38.181 --> 00:24:54.384
I knew that wasn't the place or just because there wasn't alignment If you don't have alignment, that's not going to be beneficial for you, it's not going to be beneficial for that district and your staff as well, and I think that's really important to know when you're out there seeking those jobs.
00:24:54.384 --> 00:25:02.255
You got to know who you are so you can align to that, and I think that's really important to know when you're out there seeking those jobs.
00:25:02.255 --> 00:25:02.222
You got to know who you are so you can align to that.
00:25:02.222 --> 00:25:03.287
So I think that's really really important for people to understand.
00:25:03.287 --> 00:25:03.760
I really want to highlight that.
00:25:03.760 --> 00:25:05.297
So let's talk about your work a little bit.
00:25:05.297 --> 00:25:08.608
Equity and social justice are part of the heart of your work.
00:25:08.608 --> 00:25:16.250
How do you integrate multicultural competence and emotional intelligence in the school, leadership and coaching?
00:25:17.133 --> 00:25:17.795
In the coaching.
00:25:17.795 --> 00:25:49.663
I think what's really important is knowing, or at least exposing them to those different areas If they're coming from an affluent neighborhood and looking at privileges and looking at privileges or they may be of privileged background being aware of certain biases or unconscious biases, and breaking down those barriers.
00:25:49.663 --> 00:25:51.827
It's really important to understand, okay, multicultural or multifaceted identities.
00:25:51.827 --> 00:25:52.830
What does that look like?
00:25:52.830 --> 00:25:56.144
When we say multifaceted identities, it can be well.
00:25:56.144 --> 00:25:57.576
What was our upbringing?
00:25:58.499 --> 00:26:02.387
I'm a military brat and so I traveled to different places.
00:26:02.387 --> 00:26:10.759
I went to different schools in Connecticut and California and the Philippines, so my background is a lot different, even though I'm Filipino.
00:26:10.759 --> 00:26:14.163
I have a lot of patriotism in that sense.
00:26:14.163 --> 00:26:31.762
So if I were to say, okay, what do I bring to the table, I think by going back to you or to my administrators or those that I coach, I would also ask so tell me about yourself, what's your multifaceted identity?
00:26:31.762 --> 00:26:32.746
What's your background?
00:26:32.746 --> 00:26:37.529
Does your background value education?
00:26:37.529 --> 00:26:39.234
Or it could be.
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You know, some Asian cultures value wealth more than well.
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