Analiza: Welcome to the women of color rise Podcast. I'm Analiza Quiroz Wolf, proud Filipino American executive leadership coach and former CEO of a nonprofit and Captain in the US Air Force. I'm also the author of the myth of success for women of color's guide to leadership. It's based on the lessons learned of many women of color leaders, including those on this podcast, we talk with successful CEOs and C suite women leaders of color and learn about their leadership journeys. I'm on a mission to support having more diverse leaders at the table. If you're a woman or women of color who want to sit at that table, you're in the right place. Now let's get into today's show.

I am so excited to be with Dianne Morales today. I've been following her career, and she is incredible. She's an Executive leader and social entrepreneur with a focus in education, social justice and equity. She's the founder of still rising, helping organizations increase their impact with marginalized communities. Dianne has over 20 years of experience, including being CEO of Phipps neighborhoods, and getting this running for New York City mayor in 2021. Yes, I said it. She did that. She's been recognized, including the Hispanic lifestyle. She was named Latina of influence, and she was also recognized by 100 Hispanic women nationally. Dianne holds graduate degrees from Harvard and Columbia and all the things, Dianne, I am so excited about you being here. Thank you. Thank you. Thank you.

Dianne: Thank you so much for having me Analiza. I'm excited to have this conversation with you,

Analiza: Diane, I always start with identities, because I believe there's so much power in who we are and where we come from. Can you share your identity and how it shaped your own career?

Dianne: Sure my identity now, how I claim it is an Afro Boricua. I was, you know, raised as the youngest of three in Bed Stuy Brooklyn to Puerto Rican immigrants, the youngest of three by a decade. So like by a generation, kind of, you know, youngest, and also felt a little bit like the only child, you know, blue collar family, working class family. And also, I will say that a very strong ethos around kind of like the village mentality, you know, I shared a bed, a bedroom with my grandmother until the day I left home for college. Never had my own room. And yet, there were also always people staying with us, extended family, people transitioning from incarceration, people transitioning from the island to come to New York in pursuit of, you know, the American dream, just, you know, people out of work. So there was always an extension of the family or of the village that we sort of had living with us. And I think that deeply informed my sense of kind of responsibility for others in a way that was just generous and almost mindless, in the sense that it was just sort of a given, that that was what we would do and how we would do it.

Analiza: Dianne, I want to talk about this rise because did you think back when you were growing up with your abuela, this beautiful community that you would be running for mayor. Like, was that even in the cards? Like, where did that come from?

Dianne: I absolutely do not, absolutely not. You know, I don't think I even thought about being able to be a CEO that just didn't, wasn't part of our world or our experience, or our community, although, you know, the women were the badass CEOs of their homes. And you know, the thing for running for office, for people for over a decade has been telling me, you know, you should run for office. You should run for office. And literally, my response was always like, have you met me? Like, that's not me. I'm not diplomatic enough. You know, this just sort of not my thing. And I think that there was a point where that kind of flipped to kind of like, well, that's exactly why maybe I should think about doing this, because people like me are not part of the process, and people like me are not represented. And there's something to be said for challenging that sort of expectation and that kind of like profile, and that sense that you have to be anointed or selected in order to run, because there's something undemocratic about that. And I also think that throughout the course of my career in working in sort of social impact type work, trying to sort of, you know, the social justice work, I got tired of feeling like I was tinkering around the edges. And, you know, like the work, no matter how successful, was really just a drop in the bucket, because there are still these, like, massive systems and structures that were a constant, sort of counterforce to, you know, any progress that we made. And so. So I think the idea of both challenging the system and expectations about who gets to run for office, and also the potential to be in a position to say the things out loud about what is wrong in some of our systems, and try to really push for that, I think all of that ended up kind of outweighing my sort of initial kind of rejection of that possibility that makes sense.

Analiza: So Dianne, I want to go to make it this, even for me, understanding what you're sharing is one I don't have to look like and act like the people in power right now. In fact, that is why I should be in power. So one is that's the reason I care, and my lack of mirroring is actually a strength. Two, that no one needs to say you're ready. I can declare that myself. And then three, let's get real. If we want real change, it has to happen at the system level, and that's got to be power, political power, right?

Dianne: Yes, yes. And I think that one of the things that I sort of learned I was challenging and then sort of learned in the process, is that a lot of the spaces that you know, that I identify with in terms of values and, you know, policy positions and those things, a lot of those entities, a lot of those groups, a lot of this movement, actually ascribe to the same sort of processes as these sort of institutions, you know, governmental, political institutions that have actually created some of the harm, right? And so for me, there was always kind of like a tension there in like, how is it that we can be talking about creating this sort of, you know, see scale change, but yet adopt the same systems that, you know, the oppressors have used to identify and decide who gets to do what, and who gets a seat at the table, and who gets to sort of raise their hand and say, I want to Do that. And so I think for me, that continues to be an issue, because we continue to sort of play by the rules and ascribe to the rules that have been imposed upon us. And while I get it, I also don't get it right. I feel like we really kind of have to push for sweeping change, and I'm not sure that we figured out how to do that.

Analiza: Dianne, we're going to bring up some quotes here. I know you have a quote I want to share one by Audre Lorde for the Master's tool. We'll never dismantle the master's house. So I just think that's exactly it. Let's talk about the house. And I actually got to think about new tools. And to do that, I got to get into places of power. So, I mean, I think it's, like, somewhat obvious, but yet we don't talk about it this way. And you and I have been in the social justice world, education world, for so long, and yet it's not like, hey, Dianne, what are you running for? It's more, what other role, what other partnership, what other funder Can we go after and we don't go after this whole other dimension? So I just want to say that's so important. I'm glad you're raising it. I want to talk about Audre Lorde, because she brings in so much. I'd love for you to lift up a quote that might have strike you?

Dianne: Yeah. I mean, rather than a quote, I have a piece that I read or revisited about six months ago for the first time in, I don't know, a really long time. It was one of her sort of towards the end pieces, the transformation of silence into language and action. And in that she talks about sort of getting this like diagnosis, this cancer diagnosis, and how it sort of increased her sense of urgency and also kind of freed her to find her voice and give language to things that she might not have otherwise done, because there was this sense of urgency around time and kind of like, why am I holding back? And she died, there is a quote in there about, you know, how her silence was going to be much more harmful to her than whatever sort of consequence of verbalizing what she had to say. And I have to say, when I read that it was probably February or March, it felt like the first time, and I also felt like it cracked something open inside of me and made me connect with something that I wasn't even like fully conscious of, which is the idea that I had, you know, when things with my campaign went south, there were a lot of layers that we could sort of peel back and unpack and analyze, but I think the most important thing for me is that I did not stand in my truth, and I did not speak my Peace and my voice. I deferred to others, and I was so fearful of you know, public conflict, and of you know further being in the crosshairs, that I withheld my voice. I think it wasn't until I reread that piece this past spring that I understood fully. How much harm it had caused me to sort of erase myself and defer to a narrative about me that was being created by others, and that is something that I will never do again. You know, the lesson has been so powerful and painful. You know, the journey for me to sort of come back to and find my voice has been a long and painful one. And I think one of the things that I regret the most is actually not finding the power in the moment to stand, you know, 10 toes down in my own truth, and feel like I could tell my story.

Analiza: I mean, Dianne, you bring up so many powerful points. One I want to come to is this idea of consequence, because it sounds great, right? I ran for office when I was in high school and college, and it's posters, you know, free stuff, and then you kind of promise things and whatever, you know, maybe you do some or maybe you don't, but this is a whole other ballgame where your reputation is on the line. People are saying things that are not true, alliances being formed, people that you trust, maybe they're showing up and maybe not. And so you know best. And so I'm curious if you might share, what was it like for you?

Dianne: Yeah, it was devastating. I mean, you know, it's a reminder of, like, it takes 30 years to build a career and just, you know, a couple of days to have it kind of be really, really cracked at the foundation the things that were being said to me, that the thing that was most painful is that the things were that were being said about me spoke to the very core of who I am, right about not being anti worker, anti black women. I mean, all of the things that I am and that, you know, comprise so much of the core of my identity. And so it was, it was wrenching. And the thing about that too, that's really interesting is that it wasn't actually, and this is the other sort of lesson learned for me. There were two camps, right? You know, the folks that were sort of pounding the pavement with that message, and then there were the ones that had my back to the very end, and I feel like I failed them too, by not standing in my truth, right? You know, this speaks to, I think, some of the polarization within the movement, some of the all or nothing sort of stances that people take, the inability to kind of see and acknowledge nuance, and also, like the the lack of willingness, in some instances, to engage in dialog that is constructive. And so all of this was playing itself out on a very, very public stage. And quite frankly, I think, you know, and this goes to, I think the notion of, like, I'm definitely not cut out for politics. This stuff was very personal to me. And so I was very hurt. I was really devastated that people felt like they could and should say those things about me, and in many instances that some of them had never even talked to me, ever, ever, it felt more like, oh, well, this is, you know, this is the thing to say, and so I'm going to get behind that thing to say. And that's really harmful. And I think that's one of the things that in terms of lessons learned that I feel like we need to reflect on in order to strengthen, to strengthen any kind of justice movement, right? Because if we can't sort of have these conversations amongst ourselves, if we're going to continue to sort of peel away anybody who we think doesn't 100% conform with what we want and what we believe. I don't know how we can build a coalition. I don't know how we build a real, meaningful movement. And I think that's problematic.

Analiza: Dianne, there are so few women of color who have been in those seats and experienced what you've experienced. And I'm curious, you know, we want more of you, right? And we want people to actually get the role, and then, because of that, then we can lift the next person, generation, and others up. And so I'm curious, having had the experience you've had, yeah, and imagine you do it again. And I'm curious, Diane, just taking her in now, but imagine you would be right, and you're like, Okay, I've learned. I'm going to go into this with a different frame, a different tactic, a different whatever those different things are. What would you say that advice would be, those moves would be that you'd make?

Dianne: Yeah, that's a really good question, I think. So first of all, it wouldn't be me. And that's not because of the way things went down. It's because I was always very clear from the beginning that this was a one and done proposition, that I was not interested in becoming a career politician, that, you know, this wasn't sort of a stepping stone for me to something to something else in electoral politics. I just. That's just really not kind of who I am. And I think the way things played out affirm that in many, many ways. You know? I think that's an interesting thing, right? There's some, some of the pragmatic stuff, right? Like, no matter how compelling the sort of the movement and the vision is, you do need people who understand the electoral systems and structures and who can kind of build the team, the structures and the processes to sort of execute a campaign successfully. I think, you know, because I was such a marginalized, sort of outside candidate, I didn't have any of that right. I didn't have people that were seasoned in running campaigns that sort of understood that, right? I think there's an important thing, you know, I talk about sort of rejecting institutional, you know, history around what's what's supposed to happen and what's not, but it's important to have folks who know what those things are, so that you're making an informed decision to reject that right, rather than sort of trying to build something from nothing, right? And that is really kind of who we were, you know, who my campaign and my staff were. I think there's still a lot to sort of celebrate and applaud for that, because we built what we built, despite not having any of that, not having any seasoned or experienced, you know, political folks connected to the campaign and so. So I think there's that. I think there's really understanding the context of the political landscape. It is vicious, it is ugly. And the extent to which there was, you know, they call oppo research, right? People sort of digging and looking and trying to find something that they could sort of pin. There's no amount of preparation that can really get you ready for what that looks like. You can talk about it, and you can sort of get an intellectual understanding. But being in those crosshairs is a whole other ball game. I'll give you one example of that, because the media is not above this either. There was a reporter that was trying to write a piece on me. It was sort of a, you know, a profile piece, and she was working on it for several months, and probably talked to about, I don't know, 1520 people, but she wasn't getting any dirt, right? And so it just wasn't interesting to her, you know, and she just didn't want to run with the story. She had to go 10 years back to find someone who I had terminated from a job, and focused on that story, that part of it right, the person sort of who was aggrieved, talking about feeling like they had been unjustly terminated, and blah, blah, blah. I mean, no mention or conversation about the fact that this person had committed a federal offense, right? But then the story ran right. And so there is something about that sort of context, and the sort of wanting to, like, gotcha kind of thing, and we do it to ourselves too within the movement, right? Like, you know, I remember early on being sort of questioned and challenged, like about my legitimacy around the things that I was saying about who I was or what I wanted, despite my decades of work in service to the community, right? And it was sort of the folks from the inside, if you will, who were sort of leading that questioning early on as well. So it's, it's one of those things that's really, really difficult, especially if you're coming at it from the perspective of trying to dismantle, right, or challenge those systems and structures. You know, I recognize that I put a target on my back from day one, right by saying I'm not of the institution. I'm not, you know, but I think there has to be a better way for us to put up candidates that are more reflective of us and what we want, and be supportive of them along the way,

Analiza: It stamps a few of the things I heard. Diane, it takes a certain persona strength, a special person, to be in politics, and that actually a queer arc in politics can be very powerful. That you got to know the system to change the system, and that it's ugly, and you got to look, I guess, spotless and far any little spot they can blow out of context. So it's incredibly difficult. I want to go to this point you had mentioned earlier, which is community. It's such a core value of who you are, and you have built that throughout your childhood, your life, your career, and yet, people in your community, people who you work with, who you're like this is they're gonna know I am absolutely about equity, because we've been in the trenches together, and yet they weren't to be counted on. Can you talk about that? Because we're trying to talk about coalition building, multiracial. Coalition building, right? You got me? I got you, yeah, when we go out there, left and so can you talk about that? From your experience?

Dianne: I want to be fair. There were people who had my back from day one to the very end to the finish line, unwavering, unequivocal, and it was based on them and their support that I was able to actually finish the race. So I want to be clear about that. There were also people who were afraid to get caught in the crosshairs of, you know, what I'll call cancel culture, as controversial as I know that term is, who were just afraid of being attacked publicly, of being, you know, targeted in any kind of way, of having their future opportunities impacted. And so there were a lot of people who were sort of quietly reaching out to me and expressing support, and, you know, and asking me not to, you know, not to leave the race. And, you know, affirming that they believed in me, but really kind of cautious and afraid to step up publicly. And I think, you know, the way I see that is that's a problem. That's a problem for the collective to deal with, right? That we do that, that we can sort of do that to our own and make it so that they're afraid to stand for something that they believe in. I think that's problematic. I don't think that we're building right. I don't think that we're strengthening and building when we do that. And I think that that's something that we have to really, really closely examine and grapple with and have some difficult conversations about, so that we can move forward in strength and unity.

Analiza: Yeah, because the reality is that there's a consequence. And what are we willing to do together? What am I willing to give? What am I willing to sacrifice and take a stand for? I don't think we've had that conversation because we're in these rooms where we're having retreats. We're like, it's all holding hands, and then when it comes down to it, I'm like, shoot, I might get in trouble. I'm not gonna back away. And that's real. So I think real conversation about that is helpful, so that when we get to that, those times we can say, we call we're going to call on you, like, right, together, right?

Dianne: And what is the process, right? What is, what does the process look like? I think one of the things, one of the greatest sort of ironies for me around this stuff with the campaign, was that, you know, one of the values, one of the things that I sort of put forth in my proposals and my policy platform was the notion of transformative justice. And when it came down to it, I felt like the community did not understand how to practice that. What does it mean, and what does it look like from a process perspective to you know, identify something that you think is problematic, and go through a process to address it that both heals the harm and also brings everyone together, rather than isolates and alienates.

Analiza: Dianne, do you mind sharing a concrete example? Here's how we could use it in this case?

Dianne: Yeah, I mean, you know, I'll give a perfect example,I can give two examples. Actually, one of the guys was accused of sexual harassment. We called him out on that. And there was a conversation, I thought it was being handled by one of my staff members in terms of next steps, right? Because there was a conversation around, an initial conversation around, sort of him needing to own responsibility, and there needing to be a process around, you know, reconciliation, right? What that would look like for him to repair the harm that he had caused before. I knew it. It felt kind of like nothing was going to be good enough, other than having his head on a platter, right? And while I understand right as as as someone who has also survived sexual assault, I understand those feelings. I also understand the tension when the vision that you hold, the ideology that you hold prioritizes repair over punishment, right? And so that was a sort of really specific example that was striking to me as someone who could both sort of empathize with the folks who had been impacted, but also was holding this sort of larger, longer term ideal in mind for how it is that we wanted to move things forward. Does that help?

Analiza: Yeah, that is tough, tough on both sides. I can see how you're trying to explain that to people. And yeah, people feel strongly.

Dianne: Very tough, very tough. And you know, not a lot of time invested, not a lot of turnaround invested in sorting out the process for that. And, you know, I know, I'll be honest. You know, as the candidate, I wasn't focused on that process, right? I was out. I was face, external, facing. I made assumptions about my team. How handling that and sort of navigating that process that was wrong, that turned out to be wrong, right? I thought that there was clarity and alignment around what needed to happen and how it needed to happen, and that I had folks that could handle that, and that's not what happened, right? I will find out in two weeks, right? Like, you know, people are sort of with pitchforks, kind of like, you didn't fix this, you didn't fix this. And, you know, there was a little bit of, I was definitely taken aback, because that wasn't my understanding or expectation of what was going on. But when it came down to it, I was held accountable, as probably I should have been, right, for it not being addressed. But there's also a tension there, right in terms of being held accountable when you think you have people that are doing their jobs.

Analiza: And to be clear, well, yes, we should be held accountable. There's also double standards with what you're held accountable to because of who we'll say we are as women of color versus another candidate who doesn't share our demographic. I was wondering, Diane, if you wouldn't mind, could you give some reflections on how the campaign is going, given that we have a woman of color who is going for the top seat, and is there any connection? I'm just going to leave it open to you in case, yeah, because you have experienced this and to see the debate, to see all of that come live. What are you connecting to?

Dianne: Yeah, I did watch the debate. I watched in the privacy of a hotel room because I was so anxious about it that I didn't trust that I could be in company. Can I have to say that the sort of pervasive thing that I was thinking about as I was watching and listening to her was how hard she had to work to be controlled or risk coming off as an angry black woman. That, for me, was sort of the headline, right? She had to, I mean, and there were some, there were some good moments that have become memes, right in terms of her speaking directly to him. And, you know, some of the things that were unspoken, but like understood in terms of what she was thinking, but she had to exercise a level of self discipline and control that I would argue we have never seen a presidential candidate have to exert right and that is because she's a black woman, right? You know, at times where she could have rightfully interrupted, or, you know, talked over him, or, you know, expressed some outrage, she was very controlled, and, you know, and she called him out on things right, like what, you know, she when she talked about him being a disgrace, and she talked about even the delivery of that you have to, you know, you play the tape back, was very controlled, and so I was very conscious of that. I also, you know, the other thing I'll say is that I'm conscious of her being judged as a woman around being commander in chief. And what does that mean she has to say and do and exert in order to demonstrate that she can sort of keep this country safe. And, you know, she talked about the military. And, you know, the interesting thing about this is that these are things that make me kind of cringe, to be honest, right? I don't want to sort of, you know, have us focus so much on having the most powerful, strongest military in the world. We already have that right, but I understand and I recognize why it's important for her, in particular, to assert that, because I know how she's going to be judged. Cross

Analiza: our fingers here, Diana on how things go. I so appreciate you sharing this incredible journey you've been on and you continue to be on with your organization, still rising as we are for you. We are for you, Diane, we're gonna take a little beat, and if you're ready, do some fun questions. Are you ready for lightning round?

Dianne: Let's do lightning rounds.

Analiza: Alright, chocolate or vanilla?

Dianne: Chocolate all the way

Analiza: Cooking or takeout?

Dianne: So I prefer cooking, but I'm not the cook, so I'm cheating a little bit on that one.

Analiza: Would you rather climb a mountain or jump from a plane?

Dianne: Climb a mountain for sure, two feet on the ground.

Analiza: Have you ever worn socks with sandals?

Dianne: In the house.

Analiza: How would you rate your karaoke? Skills on a scale of 1 to 10,10 being Mariah Carey?

Dianne: Oh, my God, I would say I've got some killer songs. I'm right out there in the seven or eight range.

Analiza: What's a recent book you read?

Dianne: Oh,some of us, Heather McGee, highly recommend it.

Analiza: What's your favorite way to practice self care?

Dianne: I would say that it's probably meditation or working out.

Analiza: What's a good professional development you've done?

Dianne: A good old one that I referred back to all the time and had taken all my teams through, is facilitative leadership by the Interaction Institute for Social Change.

Analiza: What's your definition of a boss mama?

Dianne: Oh, that's so controversial for me in so many ways, a boss mama for me at this stage in my life, is someone who has recognized and is striving to maintain some sort of balance between their identity as a professional and their identity as a mom.

Analiza: What advice would you give your younger self?

Dianne: I would tell my younger self to not hold back, to just go for it, that all sorts of limitations exist much more in our mind than outside in the real world.

Analiza: And then where can we find you? LinkedIn, where else?

Dianne: LinkedIn, all my social media, it's all Diane, D, I, A, N, N, E, the number four NYC. I kept that handle because it works on Instagram, on Facebook, less so on Tiktok these days, and much less so on the platform formerly known as Twitter.

Analiza: And then last question, do you have a final ask recommendation or any parting thoughts to share?

Dianne: You know, in alignment with sort of the theme of our conversation around sort of marginalized communities, women's women of color running for office. You know, someone said to me at the end of my campaign, the first one through gets the bloodiest and as the first Afro Latina to run for office in New York City. I certainly think that that is the case, but I hope that I cracked the ceiling enough to encourage others and to inspire others to sort of follow in my footsteps, and those follow that path, not in my footsteps necessarily, and continue to try to sort of disrupt these sort of norms that have been imposed on us and accepted so that we can create the change that our communities really need.

Analiza: And that's why it's you. It's gotta be you. So beautiful. Diane, thank you so much for this conversation. Thank you.

Dianne: Thank you so much Analiza, it's been a pleasure. I really appreciate it.

Analiza 31:59 Thank you so much for carving out time to hear today's podcast, three things before you go. First, if you found it helpful, please leave a five star review. Second, you can get a free chapter of my book, The Myths of Success: A Woman of Color’s Guide to Leadership at analizawolf.com/freechapter. And lastly, if you're interested in executive coaching, please reach out to me at analiza@analizawolf.com. Thank you so very much.