Season 9 Episode #15 The Real Ones: Leadership, Identity, and the Power of Authenticity with Maya Rupert

In this episode of The Cultural Curriculum Chat™ Podcast, host Jebeh Edmunds sits down with Maya Rupert—political strategist, speaker, and author—for a powerful conversation about authenticity in leadership and the often unseen dynamics of race, gender, and power in professional spaces.

Drawing from her experience managing presidential campaigns and serving in executive leadership roles, Maya shares thoughtful insights on what authentic leadership truly looks like beyond buzzwords and performative actions. Together, we explore how leaders can build trust, navigate identity in leadership spaces, and create environments where people feel seen, valued, and respected.

In this episode, we discuss:
 • What authentic leadership actually means
 • How to build trust without performative practices
 • Why identity matters in every space we lead
 • The realities of navigating race, gender, and power in leadership

This conversation is for educators, leaders, advocates, and anyone committed to creating more inclusive and human-centered spaces.

Learn more about Maya Rupert and her work here: Maya Rupert Official Website

🎧 Listen now and join the conversation.
 💡 Ready to continue your learning journey? Explore my mini courses and culturally responsive lesson plans linked in my bio.

Transcript

Copy Transcript Copied

SPEAKER_00 0:25

Welcome back to the Cultural Curriculum Chat Podcast. I'm your host, Jebba Edmonds, and this is where we center culture, equity, and real conversations that transform the way we teach, lead, and live. And today's episode is going to be one that you're going to feel in your spirit. We're joined by Maya Rupert, a nationally recognized political strategist, speaker, and author whose work lives at the intersection of race, gender, and power. She currently serves as executive vice president at Blue State and has advised some of the most influential leaders in our country. Maya has led at the highest levels from managing Julian Castro's presidential campaign to advising Elizabeth Warren. And what sets her apart is how she names the invisible dynamics that shape trust, communication, and equity in our leadership spaces. Her upcoming book, The Real Ones, explores how hidden barriers tied to identity impact leadership and how we can begin to dismantle them.

SPEAKER_01 1:38

Maya, welcome to the show. Truly, thank you so much for having me. I'm so excited to be here and to chat with your audience. So thank you, thank you, thank you for having me.

SPEAKER_00 1:48

Oh, thank you for coming. I'm just fangirling right now. I was like, wow, I'm so excited. Oh my gosh. So yes, let's talk about your work and how it focuses on authenticity and leadership. What does that truly look like for you?

SPEAKER_01 2:05

Sure. So I mean, I think, and you know, and your listeners know, authentic leadership has become a bit of it was, I feel like it's it's it's the same trajectory a lot of things go through, which is that it starts as an idea and then it almost becomes a buzzword to the point that it means everything and therefore nothing, right? So I think authenticity is something I unpack a lot in the book because it is one of those words that because it almost becomes this kind of like catch-all for everything good, it becomes really difficult to understand exactly what we're asking for. And for some of us, particularly folks of color, I would say women of any race, anyone who has had a kind of minoritized identity, what is asked for when we're told to be authentic is sometimes a little more complicated. Because for a lot of us, of the first lessons that we learned, especially in leadership positions and professional positions, was how to be strategically inauthentic. In order for me to get comfortable leading, I was very conscious that when I got into leadership positions, I was younger than was sort of normal for the positions I was taking on. I was a woman and it was a black woman. And that meant I was leading people who did not immediately see me as a leader. In some cases, they didn't even see me in some ways as an equal. And my ability to lead a team became a function of my ability to make them feel comfortable enough for to let me lead them. And that is how I learned to be a leader. Now, there's a lot of things that I do in order to make that happen that are anathema to the idea of authentic leadership. But as a Black woman, they are part and parcel to the idea of authentic leadership. And so part of what I try to do in the book is get people to understand that what becomes an authentic experience for those of us who have to grapple with that kind of double bind, that is authentic for us. And so, what are we doing to define authenticity in a way that it remains accessible to people who've had very different experiences coming into their leadership?

SPEAKER_00 4:19

Oh, that is so good. And I love how you even shared that double bind because it's like so many of us, you know, black women in leadership have to have that I come in peace trope. And I have to prove that I'm here for you and we're on the same team, right? And then I have to prove that I am the leader of said team and still have to make you feel comfortable for me to make leadership.

SPEAKER_01 4:46

And I'll come to you and I'll respect you as a leader and expert. And I don't think those are wrong instincts. I think they're great instincts. I love that I lead that way, but I also can't deny that it isn't I do it for a specific reason because I'm read differently if I don't. And so that how to be an authentic leader. So many times I'll be in sessions about that and people talking about that. And I'm like, some of the stuff they're saying just feels like it to be able to get a different language. You know, that's just not my experience. And so I think we have to be more honest that authenticity is not a one-size-fits-all experience that we all can sort of put on and it remains equally available to us.

SPEAKER_00 5:34

Yes, and I love that. And I know your book will interpret that for those that don't see it that way, but have to understand that Maya has to lead in a way that gives her the platform to be that leader, but also you have to see the interweavings of how she got here, is not the same path that others are. Oh, this is so good. So, what are some, because you talk about the invisible dynamics that you've seen shape leadership spaces, and you've kind of touched on that a little bit of, you know, how to approach your leadership role is different than a colleague would be. Can you give us a couple more examples of those invisible dynamics that you have to do?

SPEAKER_01 6:18

Yeah, you know, one of the things I talk about in the book, which I think is is again, it's one of these things that became so ubiquitous in the workplace. I think we stop problematizing how it can be a challenge, but it's the concept of bring your whole self to work, right? It's like, and and and a lot of times when people are talking about authentic leadership, that's a piece of it. It's like you should make other people feel comfortable to bring their whole selves to the workplace. Well, look, we all know that our selves don't belong in our workplaces. Yes. But we don't know which parts do, right? When someone says bring your whole self to work, you're placing two expectations on them. One is they have to show up in a way that's that is doing this, that's sort of doing engaging in this performance enough that you feel like, okay, you're a team player. You are trying to bring your whole self to your to work. But there's still this unspoken dynamic of what's considered professional and what's not. And frankly, for a lot of us, the ways that we present elsewhere are read intentionally as unprofessional in workplaces. Yes. So what it's really doing is putting a bunch of invisible labor on anyone in the workspace with a minoritized experience to say, look, yes, we do want you to bring your whole self to work, but not that part. So yes, we want you to talk about the fact that you have a relationship. But hey, queer folks, don't go too far because you might make some people uncomfortable. Yes, we want you to dress down on Fridays and let everybody see you in jeans, but don't wear your hair natural. Like, right? There are going to be those, but defining what that space is, there is nothing, there's nothing logical about it, there's nothing rational about it, there's no book that you can read and say, all right, that's what they mean. So what it's really doing is just saying all of these invisible cues, they're on you to figure out. And what is a it's a it's a kinder and a more productive way of thinking about this is the reason we want people to bring their whole selves to work is because we recognize human beings are full. So why not say what we do in our in our workplace is encourage a work-life balance. So work isn't your whole identity, so work shouldn't take up all of your time. And then you can go home and be the full version of yourself. But instead of without being completely honest about it, saying, bring your whole self to work, right?

unknown 8:56

Yeah.

SPEAKER_01 8:57

Another place this comes up a lot in the book. I talk a lot about this in terms of political leadership because I worked in politics and a lot of my experience working with candidates really formed the basis for why I wanted to write the book. And when we talk in politics, political authenticity is this like it's like the, it's the thing you need. If you ask people, it's like, oh yeah, well, you have voters want you to be authentic. But we have no shared definition of what that means. And when there's no shared definition, all it does is create a bunch of room for bias. So you have these situations where you have a leader like Donald Trump who people can say, even though I don't like him, even though I think he's lying, I definitely feel like he's authentic. Well, what does that mean? If you don't think someone's being honest, how do you read them as authentic? And when you really break that down, a lot of times what people are really describing is he's speak he's very clearly speaking without preparation. He's gonna go out and tell me the first thing that comes to his mind. Maybe those will be lies, but he didn't prepare, nobody wrote this stuff for him. But then you take someone like Kamala Harris, who doesn't speak that way. She speaks like she has prepared, she speaks like it has been scripted, she speaks like she has run this by people. And that reads to people as inauthentic. Well, those two speaking styles have as much to do with their identity as they have to do with anything else. Because when Donald Trump goes out and speaks and lies and messes up facts and misremembers details, the next day there are a bunch of people in the media who are ready to sort of sanewash everything he said because he can't he couldn't have meant all that. What he really meant was X, Y, and Z. Because he so frequently gets it wrong, we have basically started saying when he gets it wrong, we will we will do the mental gymnastics to make it closer to right. But when Kamala Harris misspeaks or gets a factor wrong, I remember she said the child tax credit cut child poverty in half. And she got fact checked by someone who said a news outlet who said it was only 45%. When that's the standard, because and and what is happening psychologically, and it doesn't happen out loud, but on some level, what's being said is well, uh, if she gets a policy wrong, on some level I'm wondering if she knows it, if she really should be here. Because when you are given the the privilege of we assume you don't know enough to be here, we assume that you are qualified, versus you have to prove to us that you know enough policy, that you're in the rooms and having the meeting, the way we experience you being scripted and unscripted are very different. So again, the decision to do something that gets read as authentic has to do with how they're perceived by people. And when that has to do with identity, it's gonna be a lot harder for a black woman to prove authenticity because she is not gonna be as comfortable being unscripted. And we see why. She is held to a different standard. Anyone can be unscripted if you're not expected to get the details right. If you have to go out there, be unscripted, and get every detail right, and make everybody prove feel like, okay, you are qualified. You deserve to be here. That's gonna be a very different experience. And that is a very, that's a much higher bar to clear. And so it's that it's those little moments where we tell some people, we've already assumed that you deserve to be here. And we tell other people, we've never assumed you deserve to be here. And how authenticity is gonna show up in those places will be very different.

SPEAKER_00 12:55

Very different. And yeah, like you said, the expectations for one person does not equal the same for the other. And yeah, the bigger the hurdle to climb over. Wow. Yeah, it is. And and again, with those invisible dynamics with your book, I can't wait for folks to get it because it will lay it out. It is out now. It is out. Oh, good, good. It is out there, yes. Congrats, yes, we will have all that in the show notes too. But it will lay it out for folks to actually see. And thank you with those examples that you shared. That to be the interpreter of the invisible barrier, you have to do it's such a mind-blowing formula that you know, people in marginalized communities are like, yep, yep, you want me to be my fool, but not to this one. I have to code switch, you know, like you know, subconsciously to make sure. And like you said, with you know, Donald and Kamala's comparison, you know, to make sure you have all the single facts, everything down, pat, and scripted, and because if you do mess up and you do go off the cuff, you get judged in a negative and harsh way. Wow. Wow. So how can educators and leaders build trust across difference without being performative, without the script? You know, it's hard.

SPEAKER_01 14:15

Yeah, it's hard. It's I mean, it's very hard. And I think, you know, it really does depend, I think, on the setting that you're in. I think there are there are ways to build this kind of trust by, I mean, the biggest thing is showcasing it, right? It's it's talking about some of these differences. People have asked me, like, since the book has come out, people are like, well, should I not talk about authenticity? I'm like, no, I actually think authenticity is very important. We should talk about it, but we should talk about it the same way we talk about a lot of concepts that we know aren't equally available, right? So if we talk about like the economy and we talk about money, we know that people are in different places with it. It doesn't stop us from having the conversation. It makes us like think more and problematize what we're saying. We would never just say, like, well, you know, it's really, I mean, you've got to have a savings account. It's really important to do it and talk about that as though everyone has equal access to the kind of money every month to put it aside and do that. Is a that's a conversation that becomes so divorced from reality that there will just be some people who check out on it. And I think that's what's happened for a long time. There are a lot of us who've checked out on the authenticity conversation because people are telling us you just need a savings account, and we're saying, wait, wait a minute, I'm not, I'm not paying my bills every month, right? And so it's talking about this stuff like it is anything else that does not come to everyone in the exact same way, and that it's not just it's on you to embrace it, right? And I think that when you when you do that, when you when you speak about it that way, when you're more conscious of those kinds of things, you build that trust because people go, Oh, oh, you're having a conversation that that like it's about me too. And once you start doing that, people start trusting your leadership, your ability to create a space that sees more people. So I think a lot of times it's just naming it. It's saying, like, we're talking about authenticity today, and I think that's really important. And I try and show up in my life authentically, and here's what I do. And at the same time, I recognize that for a lot of people, the idea of showing up authentically hasn't always been positive because your authentic self isn't always accepted in every place. Or there are times that you've been told actually do not show up intentionally as your authentic self because other people will be uncomfortable. So I'm having this conversation and I'm keeping that in mind. And I think doing that in a workplace setting, in an education setting, that is how you will get I think those are the ways that naming it explicitly will help with that.

SPEAKER_00 18:05

Yes. Oh, I love that. And, you know, let's talk about your book too, my dear, the real ones. What inspired you to write this book?

SPEAKER_01 18:15

You know, I say in the book, I decided to write the book right around the same time I realized I needed to read the book. And the reason was I was trying to describe this dynamic to someone, and I was floundering. I remember basically because what I was trying to say, it was after 2020. And if you remember in 2020, and I think we're about to have a similar dynamic in 28, because when you don't have an incumbent, everybody runs for president, and you get a huge feel. And in 2020, we had the most diverse, racially diverse presidential slate of candidates on the Democratic side. It was so exciting. And then by, you know, Iowa, it had been reduced, and we, you know, and and at the end of the day, it was, you know, it was a number of white candidates. It was, you know, two older white men against each other, and that was that. And it was kind of like, how did we go from this dynamic and diverse pool to what we had? And I was talking to a reporter who was asking me about it. And I said, you know, you know, we talked about a lot of the different ways that identity played out. And one way I was, I was what I said was, you know, I really think that this issue of authenticity, I just watched us struggle with it. I watched so many people say, you know, the candidate I worked for Julian Castro, you know, he doesn't come across as authentic. And knowing him as I did, I was sort of like, but this is who he is. You know, it's why I was I was trying to problematize that with people and not getting anything. So when I was talking to this reporter, I was like, you know, I feel like a lot of the candidates of color got attacked for authenticity and it it wasn't fair. And he was kind of like, well, but are you saying that candidates of color can't be authentic? And I'm like, no, no, no, no. What I mean is, and I was tripping over words and not able, and I realized it was because it was an argument I hadn't seen made elsewhere. So I was kind of like, wow, I someone needs to say this because it's real. There's a dynamic at play when we are dealing with politics where we say, I want an authentic candidate. But because when I think of a white male leader, I have like 50 authentic versions of that. You can be the principled war hero, you can be the like policy wonk, you can be the like young, inspiring dreamer, you can be, there are so many different models for him. But when I think about women of any race, when I think about candidates of color, I try to shoehorn them into the one or two models I've seen. And if that's true, then of course it's more difficult for me to read some people as authentic. And that's the tough thing about authentic authenticity, and especially political authenticity. We say it like a candidate has it or they don't.

SPEAKER_00 21:10

Oh, yeah.

SPEAKER_01 21:11

But it's not just about what they're doing, it's about how I, as a voter and viewer, perceive what they're doing and perceive what they're saying. So it's a two-part exploration, which means my bias plays a role in whether you get considered authentic. So that question for me dogged us for the campaign, but I didn't have a word for it. I did not have a container for stop saying this because what you're really doing is reinforcing an existing metric that only white men are electable. And it's hard to talk about because if you talk about authenticity like it's not that great, people are like, are you a liar? Like exactly. Who doesn't like authenticity? Like why? Like they're so so it was such a tough thing to talk about. And that's what made me decide I wanted to write it because it felt like I know that this is true. And when I talk to people, we all have the same, yes, I know what you're describing, but I didn't I didn't know where that argument was anywhere in the world. So I wanted to try to make it. Wow.

SPEAKER_00 22:21

Oh my gosh, I can't wait to get this book. And you know, you're so right. It is so much harder to decipher, you know, our biases with other groups of people to think of what is authenticity. And then you're also pinning your bias with the rest of the country and their biases in their check, their checklist of like, yep, yep, this this can't, you know, this candidate fits all of my boxes of being authentic. And then it's like you have your lie radar meter going, he's not from this county, or you know, this isn't his sports person he likes. So therefore, you know, it's just it's so difficult to, you know, convey that to make them feel trustworthy and worthy of that position.

SPEAKER_01 23:13

So oh my goodness, and it intersects in such an interesting way with like pop culture, right? Because our stories are also how we learn what they expand who we. Know in different communities, right? So many people. When I was growing up, you know, in the 80s and the 90s, people cited the Cosby show as such a meaningful non-black people considered that of the first black families they knew. That's the power of television, the power of storytelling. When Joe Biden said that he supported marriage equality, he cited willing grace. The ability to tell our stories and tell them in fulsome ways absolutely impact how everybody sees the world. Because if I can't rely on I've seen enough women presidents in my lifetime, you know, I've seen more of them on TV, right? So it it intersects with how are we allowing people to tell various stories on television through movies. And so it's a very similar thing. I think that creators of color and creators who have minority identities also deal with a similar issue where not all the stories they want to tell get read as authentic because everyone is wanting the same stories reinforced. And the problem with that is what we need is a broader set so that we can see that there's a lot of ways to be black in America or to be right. Like we've got to show when we see how important those stories are on our political lives and our social lives and our economic lives, culture has to be a piece of how we're expanding what we consider authentic stories.

SPEAKER_00 25:11

Amen to that. And again, to have those different pieces, multifaceted experiences that will open up the scope of others of thinking who is truly authentic because they have multiple, you know, mediums to show them different evidence of representation. Oh my goodness, Mike. Right. This is so, so fun. Okay. Last couple questions for you. Where can we find all things Maya Rupert? And where can we get a copy of your book, The Real Ones?

SPEAKER_01 25:45

The book is out and down. It is it's uh so to you know, go to your local book bookstore and pick it up or order it online. The easiest way to find everything I'm doing, you can go to Maya Rupert.com. You can order the book from there. You can also see, you know, my limited series podcast is they are unavailable. All episodes are are out now. We talked about how women of color are running for office in unconventional ways and winning. And see more of my writing. You know, I I often will I write, I will be doing it more, but yes, like I'll write op-eds, things like that, and that's all available on the website now.

SPEAKER_00 26:25

Love that. And I will definitely have that in the show notes for everyone in the description so folks can continue to follow you in this great work. And one last question for you, Maya, before we wrap up. What is an example of a real one in our community that is doing all the things? Yeah.

SPEAKER_01 26:50

A real one in our community. I mean, I will say this. I dedicated the book to my sister. My big sister, Imani Ripper Gordon, is the president of the National Center for LGBTQ rights, formerly the National Center for Lesbian Rights, if folks are more familiar. That's a national organization that engages in impact litigation, public education, legislation to work on behalf of the LGBTQ community, but specifically from a feminist lens. They were feminist-founded, and sort of that remains a huge part of their of the work that they're doing and really pulling out the intersections of the ways that you know misogyny and like continues to hurt folks in the LGBTQ community and beyond. So she leads that organization with a level of grace and thoughtfulness and just she comes at it from such from such a space of abundance and it shows in all of their work. And so I'm I've got to name her.

SPEAKER_00 27:52

Oh, yes. Oh, it's so nice to have, you know, a big sister to look up to and to deliver her flowers. That's amazing. It's my favorite thing in the world. Oh, that's amazing. Oh, Maya, this was such a fun and thought-provoking conversation. And it did, it got me in my spirit because I'm like, yes, being in those shoes of as an educator and leader in my community, it's just been amazing to, you know, feel like, yes, I'm heard. I can't wait to get your book and you know, highlight it and share it with folks so they can also, you know, share the real ones. Because yeah, our real ones need to stand up and show up and show out. Yes. You know, yes. Oh my goodness. And yes, thank you all for listening today. Thank you, Maya. And if this conversation resonated with you, I invite you to take it deeper. My mini courses and cultural responsive lesson plans are designed to help you, educators, to move forward from intention to action. And those are also in the show notes below that you can find. Don't forget to subscribe and share this episode with your colleagues and the real ones in your life. And until next time, keep centering culture and leading with purpose. Bye bye.