WAYNE BROWN: Hello, I’m your host, Wayne Brown, and welcome to the ET project. We’re delighted to be delivering this podcast for executive talent all over the world, whom we’re affectionately referring to as Team ET. Today, we’re flying into San Leandro, California, and chatting with our guest, Dr. Cynthia Rapaido. Dr. Rapaido is a distinguished educator and leadership coach with over 30 years of experience in K-12 education and higher education. She holds a doctorate in international and multicultural education and a master’s in educational administration from the University of San Francisco. Cynthia has served as a high school principal, assistant principal, and classroom teacher, providing a comprehensive understanding of the educational system across diverse school districts in California. Her work extends to higher education, where she has contributed significantly as a faculty lecturer, dissertation advisor, and field supervisor of top-tier institutions. Cynthia is known for her commitment to equity in education, student success, and inclusive school leadership. Her debut book, ‘Step Up Your School Leadership Game: The New Administrators’ Guide,’ is now available on Amazon, offering aspiring and new administrators real-world strategies for success in today’s evolving educational landscape. Team, through this conversation, we’ll be exploring sections of Cynthia’s book and getting introduced to a new personality model, as well as discussing multifaceted identities. This is a real opportunity to learn a little bit more about yourself, as well as those that you manage, using a really interesting set of communication and engagement tools. I know you’ll enjoy it.

INTRO: Welcome to the ET project, a podcast for those executive talents determined to release their true potential and create an impact. Join our veteran coach and mentor, Wayne Brown, as we unpack an exciting future together.

WAYNE BROWN: Hello, team, and welcome to this week’s episode. As you can probably hear, I’m suffering from the flu, so my voice is very croaky. Hopefully, my guest can do all the talking for me, and we’ll get through this episode. But I’m really excited about our conversation, as it builds so nicely on last week’s discussion on mindset. And let me ask you a couple of questions to start with: have you ever left a meeting feeling like your team was speaking somewhat of a different language, perhaps? One person wants immediate action, another wants endless data, and all you can see is probably the big picture or the vision. Most likely, it’s not them or you that’s the issue; it may be a lack of a shared framework for understanding each other and each other’s wiring. And today, we’re going to be introduced to a new framework, and it helps us to explore and diagnose our leadership style, our core operating system, if you like, and understand how we can decode others in the process. It’s the first non-negotiable step, perhaps, for turning friction into flow on your journey to better leadership. And joining us to unpack this is education and leadership expert, Dr. Cynthia Rapaido. Cynthia, welcome to the ET project, first of all. 

CYNTHIA RAPAIDO: Thank you so much, Wayne, for having me. 

WAYNE BROWN: The intro that I just mentioned rings so true for many of our leaders who are our audience, by the way. And the reason we’re talking primarily is because of the book that you released a short while back; it was titled, ‘Step Up Your School Leadership Game: The New Administrators’ Guide, Lessons to Navigate Big and Small Challenges with Confidence and Purpose.’ It’s a mouthful, Cynthia. But as I understand it from our last conversation, the book was born from over 30 years as a teacher, a principal, and now a coach. Was there a specific moment or some sort of recurring frustration in your career that made you think, we need a better language to communicate and understand each other? 

CYNTHIA RAPAIDO: Yeah, there was a point where I felt I didn’t really have much of a voice, and I was second in command, but there were two of us in second command, and why am I not able to express myself more directly? And I was waiting for an invitation to say, “Cynthia, so what do you think? ” I mean, that’s kind of the proper way that I was raised, like, wait until you get asked. But as a leader, we just kind of jump in and just start talking over each other. 

[00:05:00]

WAYNE BROWN: Yeah. 

CYNTHIA RAPAIDO: And I had to kind of try to understand the different people and the different dynamics and yet still be patient enough to hear what they have to say as well as I wanted them to hear what I wanted to say. 

WAYNE BROWN: The process of writing the book—how was that experience for you? I’ve been involved in writing a couple myself. I know it’s a journey. Did you really enjoy it? Or was it really a labor of love, and you felt the message needed to be shared? 

CYNTHIA RAPAIDO: Both. I really enjoyed writing it because it actually helped me reflect of stories that happened, and there are a lot of vulnerable stories that I talk about. But those are lessons that I learned, and that’s how I learned how to become a better leader, not just through the first section, but just through all the different things that we don’t know what we don’t know until we do it. 

WAYNE BROWN: Yeah. And true to your career, I duly noted the homework exercises at the end of each chapter. Thank you for that. We’re going to focus primarily on chapter one, which is really the foundation for everything that follows in the book. And it’s where you introduce the model that I mentioned; let’s jump straight into it. It’s called the Fruit Leadership Chart, an interesting name, perhaps you can introduce the framework and just the overall overarching methodology behind it. 

CYNTHIA RAPAIDO: So just the big picture of it is there are four main fruits, and we may have one dominant type of style or leadership framework in that sense that dominates us, or we might have two or three. But as a, like a school leader, we need to be able to know all of those skills and styles so that we can be explicit with each other, how to best work with each other. And even though we’re different, it’s a synthesis as opposed to, oh gosh, you’re frustrating me, and I’m frustrating you. 

WAYNE BROWN: We’re all exposed to a large number of different tools and frameworks out there in the world. What was missing from the existing tools that you felt I really needed to create something myself here to nail the issue? 

CYNTHIA RAPAIDO: I think what it was is there are a lot of things that help identify strengths and blind spots, but I didn’t really see how I can grow, except for knowing that, let’s say, I’m an introvert or an extrovert, and it’s now labeling me as one or the other. This way, I can be both; I can be an introvert and an extrovert depending on a situation and depending on who I’m with. And so that’s why I wanted to develop the Fruit Leadership, because we can be all of those or at least see our blind spots and go, okay, I need to develop this because I realize I’ve been that all along. 

WAYNE BROWN: Before we jump into the actual methodology, was there a moment in your own career where you realized, “Ah, this is somehow my leadership style? Was there an aha moment where that crystallized for you? 

CYNTHIA RAPAIDO: Yes, it actually was before I even came up with the fruit because I would think, “Oh, I’m this way, this type of style where I’m sensitive to others, that emotional intelligence and listening and looking for harmony when we talk. And I thought, hmm, what kind of fruit is that? What kind of fruit looks like that? So that’s where I started to visualize. 

WAYNE BROWN: Well, once again, the four styles, so we have the apple, grape, pineapple, and the orange. For me, the model’s power isn’t just in the labels; it’s in the guides that you create to go with this methodology. And you have it as a quadrant, so most people can visualize the four quadrants and each fruit in one quadrant. 

[00:10:00]

WAYNE BROWN: And you have on the chart areas to develop; let’s say it’s an apple, and you tell them to be patient and learn how to be more patient, or a pineapple, and learn to be more deliberate. Why is the framework so important to be seen not through the eyes of weaknesses, but as a conscious growth tool? That’s how I interpreted it, at least. 

CYNTHIA RAPAIDO: Yes, and that’s exactly what it is. It’s not so much of a… It’s a blind spot that we might not even realize how we behave with others. 

WAYNE BROWN: You also have a brilliant ‘how to best work with’ in the guide, right? So, if I’m an orange who needs to get a quick decision from an apple, what’s one piece of advice from that guide I must remember? How did you start to piece all this together? 

CYNTHIA RAPAIDO: That was because I would think of these people, why am I having difficulties with certain styles?” And why aren’t they like me? And then I would think, okay, when I see them, then I need to either develop some more styles that are similar or mirror them so that way I cannot get frustrated or they get frustrated with me. 

WAYNE BROWN: Right. 

CYNTHIA RAPAIDO: And we can now become productive. Again, it’s that now synthesis as opposed to when I think of cultures, it could be cultural asset, cultural differences. Yeah, so similar in that sense, where we can synthesize. 

WAYNE BROWN: Right. And it makes perfect sense, as I was going through, and I was seeing that unfold. Maybe if you don’t mind, could you give a little bit more detail for each of the four fruits and what is unique about each one, and how does that sort of play out in our life or in the real world? 

CYNTHIA RAPAIDO: Oh, sure. So, I’ll go through that, the framework, now. Well, thank you, Wayne, I’ll ask you to be a part of this so that your audience understands i,t too. So, you referred to, or my book refers to, the four different types of fruit, and you did say, “Yeah, there are quadrants in the framework.” So, apples, grapes, oranges, and pineapples, and just without even going into any details of it yet, which one most resonates with you? 

WAYNE BROWN: Yeah, I like that question because as I was reading through it, I was thinking to myself, before I went into the discussion, I said, “Gosh, which one will I pick if I just had to pick a fruit that represented me? ” I think I came up with orange. 

CYNTHIA RAPAIDO: Orange? 

WAYNE BROWN: Yeah. 

CYNTHIA RAPAIDO: Okay. And then is there a secondary one? 

WAYNE BROWN: Probably the apple. 

CYNTHIA RAPAIDO: Orange and apple. So, I’m going to describe, based on how my book describes it, those two fruits, saying that when you think of… well, I won’t even go into that detail yet, just thinking about what they look like. So, an apple—I’m going to start with the apple because that’s kind of how we started off. An apple is such a simple fruit; you can just take the apple, wash it, and then just chow down, and you’re done. Fast, easy, simple action, nothing else to do with it. And then when you think of grapes, grapes are on one main branch, and there’s a bunch of them that are clustered together, they’re grouped. So, when you think of grapes, they’re more like group consensus, harmony, equality, and equity—everybody is equal. And they all taste the same; when you eat one, they’re all the same flavor. And then when you have an orange, an orange is very complex; you have the exterior, but once you even open that up, it’s very organized, and even the pulps are organized; it’s very detailed, it’s meticulous—that’s the orange. And then the pineapple, it has a bunch of eyes on the outside and this big giant crown on the top. And so when you visualize that as a characteristic, the eyes are visionary, have lots of ideas, and think of all the different possibilities; they are very different from the other fruits, so that’s those.

[00:15:00] 

CYNTHIA RAPAIDO: So now, when I ask you, based on what I described, which one describes you? Which one now resonates with you?

WAYNE BROWN: I think I nailed it; I’m more of an orange. I’m definitely more of an orange. 

CYNTHIA RAPAIDO: And you know what’s interesting? Most people that I’ve talked to when I do this exercise, the same fruit that they initially picked is the same fruit that they identified with. 

WAYNE BROWN: Wow!

CYNTHIA RAPAIDO: And so, based on those characteristics, then if I were to tell you, “I’m a grape,” you might say, oh, okay, well, Cynthia is a grape, and now you’re an orange.” So, knowing that you like details, or you are into details, and you like things systematic, in place, and organized, then I need to shift my way with you, be able to organize my thought process, and put things in place so it makes sense for you. And then when I ask for you to understand me, also be reflective by asking me what I think, and be inclusive when I’m in a group together with you. So that’s just one example. 

WAYNE BROWN: Right, and it links to the simplicity, and it provides a lot of clarity. If you’re working with leaders introducing this, how quickly do they typically pick up on it? 

CYNTHIA RAPAIDO: Oh, very quickly, very, very quickly. And sometimes they laugh about it. And then I have stickers, and I say, “There are these four different fruits; you can pick one if you want,” and they go, “I want all of them.” They want to be all of them. And I say, “Then you can focus on that.” I know that I was not a pineapple for sure, but becoming assistant principal to principal, I needed to make sure that I’m the face of the school, so I needed to make sure that I know what the direction is and share that with everybody: “Here are the goals, here’s what I see happening. And then working with the different people and saying, “Okay, so what do you see?” “What do you see?” “How can we get this in place? “And then the apples would put things in place and say, ‘This is what we need to do; let’s get this done.’ The apples are the action-oriented; they want to implement and execute, and just get it done. And then the oranges would want to go, ‘Wait, let’s put this in place.’ So, like in September, we’re going to do it like this and then October… So, they wanted to put things in place, and then the grapes would want to make sure that everybody is included. 

WAYNE BROWN: Right. How do you start the conversation around the whole chart concept? Is there a lead-in that you have that helps people gravitate towards the principles behind what you’ve created? 

CYNTHIA RAPAIDO: Well, when I first start up, even in my first chapter, I talk about it’s important to know yourself as a leader, know what you stand for, know your purpose. And then to do the leadership role, what is your style? And know those strengths so that way when you’re in a situation and you have conflict with somebody else, what is it? Maybe it’s one of these other fruits that they’re having trouble with and then being able to mirror it and then it becomes easier to have a conversation. 

WAYNE BROWN: Yeah. So, if I was working with you as your client, how long would you spend introducing the model before I could become fairly proficient in it? 

CYNTHIA RAPAIDO: I think it’s really quick. Now that you know this concept, I think you can ask your friends, you can ask your colleagues, your own colleagues, your family members, and then it’s just applicable immediately. 

WAYNE BROWN: Right. Let’s move on to the item you mentioned a little bit earlier, multifaceted identity and the whole diagram, you have a diagram in the book. I guess my first question is, why isn’t it enough just to know behavioral styles? Why should we explore our identity and the whole upbringing, the culture, the life experiences? Why do we need to go to that next level? 

[00:20:00]

CYNTHIA RAPAIDO: Again, it’s more of that awareness of self and awareness of others. So, there may be a lot of differences between me and anybody else, but also there might be some similarities. And then there’s also a way to have a better understanding and that’s where the emotional intelligence comes in and you go, “oh, so Cynthia, now I know a little bit about you and your family background and your upbringing.” So, I think that makes a big difference when you know a little bit more about the person because now you’ve personalized it and not just stereotype them. 

WAYNE BROWN: Yeah. Does one proceed the other? Like, should you know your fruit style before you look at your identity or do you benefit more with your leadership styles if you know your identity? Like is there either or is it a both end? 

CYNTHIA RAPAIDO: I think it’s both end. If I were to do my siblings, I already know where we stand in terms of multifaceted identity. But when I ask my siblings, what fruit do you think you are? After I started to write the book and try to analyze my own siblings, I would think, yeah, this is them; they’re an orange, that one’s an orange, that one’s an apple, that one’s a pineapple. And it just made it much more easy and funnier to do and I can see how we can bicker and get frustrated with each other because one is just so detailed. It’s like, let’s get over it and then the apple of my other sister like, “let’s go, let’s go.”

WAYNE BROWN: One of the things that I was imagining in preparing this was we all suffer from unconscious biases. And I think identity and understanding yourself, self-awareness and leadership styles, these are all great opportunities for going deeper to uncover some of those biases that we may not always realize we care, do you touch on that at all? 

CYNTHIA RAPAIDO: The unconscious biases, when I’m doing coaching, I do. Like I’ll mention, well, why did you choose that student? Or why are you disciplining that student? Why are you just focusing on that side of the classroom and not this side of the classroom? So, I do want to bring that kind of awareness out when I’m doing my coaching. I think it’s important because they might not even realize that there’s some kind of bias that they don’t know. 

WAYNE BROWN: Right. We’re speaking primarily about one-on-one or individuals looking at individuals. But I’m wondering also, I can imagine there’d be considerable impact for a team to start to uncover this as a collective rather than as an individual. Do you work much with teams, helping them identify or start that conversation?

CYNTHIA RAPAIDO: I haven’t done it lately because most of it is more one-on-one. But when I did work with my teams, we would talk about our differences, we would do like the Fruit Leadership Style first, which is a little lighter. And then when we talk about, well, when you work with somebody, why is that? And maybe it’s part of their culture, they might have been… or their upbringing, this is how we were raised and I’m trying to bring that awareness to the group. 

WAYNE BROWN: Right. For me, when we talk about identity, we often say that we have multiple identities, we assume an identity for a role that we’re in in that instant, for instance, I’m a father, well, with my daughter, I don’t lose that identity but specifically in that moment, I’m acting as a father, when I’m playing or guiding or working with my daughter. I’m a husband as far as with my wife. I’m a coach, that’s another identity, I could be somebody else in society, et cetera. Does that also fit within this multifaceted identity model or discussion? 

[00:25:00] 

CYNTHIA RAPAIDO: Absolutely, absolutely. It doesn’t have to be all those isms like gender or gender orientation, it could be religion, it can just be your upbringing or just male, female identity. But it could even be our hobbies and interests. And we go, “oh, I didn’t know you like fishing, Wayne.” Or something like that. And you would ask, “oh, I didn’t know you like dancing, Cynthia.” I’m like, “oh, yeah.” “What kind of music do you like?” I mean, it could become a discussion where we can now like, okay, if we were to identify common ground, we might find out, oh, we both like traveling. 

WAYNE BROWN: Right. It is a great conversation, Cynthia, I have to say. I mean, everybody likes to talk more about themselves than they like to talk about other things. If you have the ability to start the conversation, trying to understand the other person in greater detail, it’s the first step to building that trust and building that relationship and really building the understanding. I think the tools are simple, but they’re so effective and I really, really enjoy getting to understand that more. What does the rest of the book talk about? So, this is chapter one we’re just talking about, just in general, what does the rest of the book introduce without going too deep? 

CYNTHIA RAPAIDO: So, there’s like five main sections of the book. So, the first one is about knowing yourself. And then once you get into a position as an administrator or a school site leader, then you hit the ground running. So, it’s like, okay, what do you need to do once you get the job? You only have one week to prepare, what do you do? So prioritizing, meeting the people and knowing the grounds. And then the next section is the nuts and bolts, so what paperwork do you need to know? What kind of details? That’s the orange stuff. What are the details? The website. What are you conveying out? Details, details, documents, everything like that. And then the next section is about those we serve, which is the students, the parents, the faculty and staff and how to engage them and build trust. And then the very last part is time, space and energy, which is self-care, being organized, how to get organized if you’re not organized. And then just embracing the role as a school leader. 

WAYNE BROWN: And the one thing I would say to our listeners, who are predominantly leaders, is that although Cynthia’s book speaks directly to the administrators, the principals of schools, it is very applicable to leadership in general. And that was my takeaway is that you can apply the book, I guess as simply, or you can take parts of the book, worst case and apply them to your own leadership role. So, I think the book has value for everybody. I’m curious, Cynthia, when you are working now as a coach and a school connects with you and says, “Cynthia, come and help us, we have a problem.” When I look at the fruit model, it’s a very holistic picture and I would imagine if we had a component of each quadrant, we’re more balanced, that might be my interpretation and I may not be 100% correct, but in general, is there one particular fruit that you find most often that’s missing from the leadership table? 

CYNTHIA RAPAIDO: Not so much, no. And there are some of that overlap, like their primary, secondary and as we become more and more as a leader, all of those skills become almost like a fruit salad, if you want to call it that. We become all of those because we’re not like stuck in one role, but we’re doing all the roles or we understand all the different components of what we need to do as a leader and we can actually handle all of those. 

WAYNE BROWN: Right. Now I’m going to put you on the spot and ask you to give me advice, let’s say I’m an orange, you come in, you’re working with me, I love the detail, I love the structure, I like to understand as much as I can before I jump in, not necessarily make a decision before I really commit, how do I soften that a little bit? How do I become more agile? 

[00:30:00] 

CYNTHIA RAPAIDO: So, in my book, I’m going to find the exact page for that, this is found on page 24 of my book, if you are an orange, you need to be more flexible because you are looking at systems and putting things in place. And if people come up to you, then be more open to ideas and discussion and communicate that gently. Because if you’re working with a grape, they might go, “God, you just need things as is,” how about… or if you’re going to give advice to somebody or you want to critique something, you can soften your tone. 

WAYNE BROWN: You’ve described me beautifully. I have a colleague who will come and talk to me and they’re very abstract and almost the opposite of me. And for me, I have to be able to bring structure to the conversation. So, as they’re talking with me, I’m thinking to myself, so, Elise, they mean this, this and this, right? I’m trying to bullet point it, simplifying it. It’s not the most adhering trait that I have, but yeah, good advice for sure. You also have sections where you talk about budgets and safety and engagement. 

CYNTHIA RAPAIDO: Yeah, I forgot about that

WAYNE BROWN: Let’s pick on say, parent engagement, because I know as a parent, we’re just on the way to parent-teacher conversations in a couple of days. So how does the teacher, how does the principal understand their own leadership styles or fruit styles and their identity? How can they change their approach to my particular personality and style when they don’t really know me? So, they only have a very short window, maybe a 15-minute window for our conversation, how do you become better and more effective at really running this conversation and doing it very effectively and quickly? 

CYNTHIA RAPAIDO: A good question. Well, I think in terms of trying to understand where you’re coming from, I would even encourage doing that same exercise, it can be really quick and see what they gravitate towards. And then it’ll just be easier as opposed to guessing your style, how to work with you. 

WAYNE BROWN: Understood. So, it’s very intentional, is one of my takeaways. So, as a leader, knowing yourself is one thing, but then we have the social awareness and the engagement relationships. We have to be intentional about trying to understand the other person and understand their style, is one of the things that maybe… 

CYNTHIA RAPAIDO: Absolutely. And I think even if you were to ask the principal of the school, if that were the exercise, I mean, if you were to ask, so what are you? So, we know how to best work with you too, it would just be openly explicit and intentional, it’s just easier. 

WAYNE BROWN: Right. Let’s paint a slightly different scenario, let’s say that the principal or the leader is coming into a meeting, how might they run a 30-minute meeting introducing the first styles? Like as a starting point to really create team harmony, bonding, whatever. What would they do as a starting opening to bring it to the table? 

CYNTHIA RAPAIDO: So, if I were to do it with my faculty and staff, I would do similar what we just talked about, but I would probably have everybody listen, well, here’s my four fruits, which one? There’ll be a table over there, that’s an apple, those are the oranges, pineapple. And which one gravitates to you or resonates with you? And then just have them go to those tables and say, “okay, why did you like it?” And then let them talk, why do you like that? 

[00:35:00]

CYNTHIA RAPAIDO: And then now I’m going to talk about the characteristics or the qualities and then say, now move to the table that resonates with you now that there’s a descriptor. Now, not very many people may move because they’ve already identified and go, “oh, that’s me,” but then you might see some movement. And then having then listed what helped me was I actually asked my faculty and staff, put your name on so at least after I have 80 staff members, I know how to work with you. If you’re a pineapple, “oh, boy, okay, you’re very visionary, I need to kind of like bring you back down and let’s put things in place.” And if you’re the orange, then let me pull you this way and let you look outside of the box because you’ve been this way. But it helps with that dialogue once I need to meet with them one on one or once they are a department team and… they might all like science, but they all may be different fruit styles and then they can learn how to go, oh, okay, now I know why I have some kind of friction and how I now get past this and we can work as a team.”

WAYNE BROWN: Right. I’m curious, I’m always curious, but I’m curious about your own journey and how creating the model and your understanding has changed your own perspective about how to lead differently. 

CYNTHIA RAPAIDO: Yeah, it has. And I think it has gotten even better. And so even when I’m meeting with new administrators and they’re trying to learn the new role that they’re in and work with their principal, who might be totally… I mean, it’s all new. Then I would ask them, “what are you and what is your administrator?” Because if they say, “oh, there’s a lot of conflict” or “we don’t get along” or “we’re butting heads.” I say, “well, it’s okay to have a discussion, but what is it?” And then we find out, oh, and we actually work it out almost like a little… not counseling session, but now it’s that awareness. And the principal will come in and go, “oh, yeah, yeah, yeah, I need to be not so much of an apple with my assistant principal.” So, they actually become aware and they’re not even the ones I’m coaching. 

WAYNE BROWN: Where can people find the book? On Amazon, I’m guessing, or where? 

CYNTHIA RAPAIDO: Yeah, they can find it on Amazon; there’s a paperback, there’s the audio and there’s the Kindle. 

WAYNE BROWN: Well, Cynthia, a great conversation. I highly encourage everyone to go out and get a copy of the book, there’s lessons most definitely for all of us. I’ve widely read in this regard and I took so many lessons and so many notes from the book, so I’m sure everybody will find it useful. So, thank you for generating the book in the first instance and thank you for being a guest on the ET project. 

CYNTHIA RAPAIDO: It has been a pleasure, Wayne and I’m so glad that you invited me to come on. Thank you so much and thank you to your listeners as well.

OUTRO: Thank you for joining us on the ET project, a show for executive talent development, until next time, check out our site for free videos, eBooks, webinars, and blogs at ‘coaching4companies.com.’

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