How Leticia Peguero Builds Cultures of Care and Transformative Leadership in Philanthropy
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Leticia Peguero, vice president of programs, Nathan Cummings Foundation.
In my first days at Nathan Cummings Foundation, Vice President of Programs Leticia Peguero initiated a conversation among the program directors by asking us how the purpose of the directors’ meeting was distinct from that of the program team meeting. Even though I was new to the foundation, my views were listened to and given the same consideration as my colleagues. By the end of our conversation, the directors had unanimously agreed to abolish the directors’ meeting and move all discussions and decision making to meetings attended by the full program team. In creating an opening for self-reflection and reimagination, Peguero encouraged a powerful shift in practice that was grounded in our collective values, and value, as a team. That small encounter with transformative leadership confirmed for me that I’d come to the right place.
Creating the conditions that enable courageous transformation is a tricky thing, particularly in a sector like philanthropy that is notoriously slow to change. In a field where 92% of foundation presidents and 83% of full-time staff are white, many are rightly questioning whether philanthropy is equipped with the leadership it needs to make progress on social justice and racial equity. The sector won’t change with more of the same. It needs people who can be translators and build sturdy bridges between boards, staff and communities. Peguero’s leadership reflects a moral clarity, intentionality, skill and vision that is as durable in a storm as it is on a sunny day.
Though I’ve since left Nathan Cummings Foundation, and Peguero recently announced that she’ll soon do the same, I continue to learn from her plainspoken truth telling, ability to generate the right conversations, and capacity to build leaderful teams. As philanthropy keeps grappling with new understandings of old problems, and what it takes to create meaningful change, I spoke with Peguero about working with purpose and integrity, learning to navigate white supremacy in the workplace, and cultivating ways of being that build trust, care and accountability.
Tell me about the path that brought you to philanthropy.
Leticia Peguero: As I think about my journey here, you could say that I fell into philanthropy by accident. I actually didn’t even know what philanthropy was, but there was someone there who saw something in me and took me under her wing. I was born into a family that had just gotten here from Puerto Rico, and as a kid, I had a particular set of sensitivities that allowed me to pick up on things that were unsaid about what it meant to be in a family of women that were poor, that were workers, and that were piecing together their lives. I am the first generation in my family to go to college, so working in philanthropy wasn’t just an amazing opportunity where I met a lot of great people. It was also discovering that there was this whole other world that existed, and that needs people who come from the communities philanthropy is trying to impact.
Intention is a relatively new thing in my life. In the last decade, I’ve been much more intentional about who I want to be in community with, what I want my life to feel like, and how I want to express love, including through my work. I also grew up kind of adjacent to religions like Ifa and with a belief in African deities, and if you believe in that sort of thing, which I do, it has been almost like there’s a group of ancestral women that are always with me and moving obstacles out of my way. These ancestral deities have been leading me in directions that may seem random, but actually aren’t.
What was the purpose you wanted to fulfill by working in philanthropy when you entered the sector, and how has that purpose changed as your leadership has grown?
Leticia Peguero: When I entered philanthropy, I thought it was going to be for a short amount of time. I remember walking into the Robert Wood Johnson Foundation with another National Urban Fellow named Catherine West. We got there early and had been talking with excitement outside in her car, but when we walked inside, it was one of those places that felt like you had to whisper.
I knew working at the foundation was going to be an opportunity for me to learn, and Debra Perez, who picked me for the fellowship, is a powerhouse, so I didn’t want to let her down. I got to see how the sector works and become a conduit for the organizing and direct service happening in communities that I care about. I felt like my purpose was to be a translator between these different worlds. My purpose was to find groups doing excellent work and make arguments for why they should get funded.
Through the process, my leadership has grown and changed. Even though I continue to see myself as a translator, lately, I’m in a place of finding new purpose as I think about the field as a whole and as this moment shifts. I want to make sure my translations are for the right end user. That has often been the case, but sometimes I’ve spent a lot of time translating for an end user that is not who I need to be focusing on right now.
What have you learned that has enabled you to work in alignment with your purpose? From what you just shared, it sounds like you may still be learning.
Leticia Peguero: I’m still learning, for sure. Going into philanthropy is hard for people of color. And for people of color who really care about their community and have some analysis of critical race theory, it’s a hard place to be because you’re confronted with, not just white people, but whiteness in its entirety. I had never worked in a place that was so white, literally and figuratively. So, I had to learn how to stay grounded and to own my own identity.
I also had to unlearn all the things I had learned about what it means to speak with an accent or to wear your hair a certain way. In the beginning, there was a lot of self-doubt. When should I talk? Should I say this thing? Do I tell somebody that they’re wrong about something—because what she just said isn’t really what happens in community. It’s been an incredible journey that has led me to feel really grounded in my identity.
The other side of that is having to then translate that for your community because people have very skeptical feelings about people like me who work in community and then go into philanthropy. Either you’re not cool, or you’re very cool and people want to hang out with you because you know where the money is. It took me years to go through a process to really know who I am in this space, what is mine to put down, what belongs to others, and how to be grounded as I move through these spaces that are sometimes incredibly oppressive and other times are incredibly uplifting.
Philanthropy’s interest in diversity, equity and inclusion has grown exponentially, particularly over the last 18 months, and in some ways, that’s because the sector has been made to confront how it’s been shaped by and perpetuates white supremacy. How do you think about the value of DEI initiatives, and what’s at stake if they fail?
Leticia Peguero: In my opinion, the way that DEI initiatives have evolved is bullshit. I don’t think that was the original intention, but there’s been incredible mission drift and a commodification of DEI that, like anything else you commodify, has made it lose its integrity. In the DEI world, there are some amazing trainers and facilitators that are engaging in the work from an incredible place of integrity, but for the most part, you get people who do really good frauds. There are lots of one-time trainings, box checking, and funders replicating what they see fellow funders doing. None of this is what the original intention was, which was transformation and justice. It was about understanding our biases and the ways white supremacy works in different spaces and places in history. We can acknowledge that philanthropy comes from a legacy of oppression and still do good with the money.
If DEI fails, I think we’ll be in the same place we are now. There are a lot of terrible practices in philanthropy. This is true about dynamics between funders and grantees, but these spaces can also be fairly toxic for those who work in them—and not just for BIPOC folks, but for anyone trying to change things in their institution. Philanthropy is stuck in this old, hierarchical model that we know doesn’t really work. It’s still trying to emulate business practices that come from chattel slavery that even the business world isn’t trying to do anymore. So, if it fails, we stay stuck in place.
The big danger, and we see this all the time in philanthropy, is that when something fails, funders use it as an excuse to not try again. There are still people in philanthropy who say they can’t find Black leaders to fund. There are people who say that they tried to fund Black organizers, and because we still have white police officers murdering young, Black men a year and a half later, that experiment failed, and they move on to the next thing. So that is the real danger if these DEI initiatives fail.
What do those who work in philanthropy need to do to ensure these processes don’t fail?
Leticia Peguero: One thing that’s needed is really good white accomplices who are aligned with a courageous vision of what’s possible. Sometimes, people of color need white accomplices in the room to say the things that we will be expected to say, but that will land differently when a white person says them, especially when it’s said by a white person who has positional power in the organization. Those are moments when people of color don’t have to carry the burden of saying something, and when something is said, it’s heard differently.
As someone who’s been in leadership roles within different foundations where you have facilitated these processes, what are some approaches you’ve found useful?
Leticia Peguero: If I’m stepping into a leadership role, I would think about it like an organizer. The first thing I would do is create a power map of the environment that would provide an understanding of how things got here, who has what power in the space, who needs to be an ally, and who is going to have my back. I would also think about what the pace is that’s needed to make change happen. Without that analysis and vision, we fall into potholes.
I drive and live in the Bronx where there are terrible potholes. When you don’t see one, you get jolted. You’re afraid that the eggs just cracked in the backseat or that your muffler got damaged. For me, I’m very aware of what’s in front of me and what’s coming next. Sometimes, there are opportunities to drive around a pothole safely. Sometimes there aren’t, and you just have to suck it up and brace for the impact. And sometimes, if you’re paying attention, you can create the space to avoid it.
When I was executive director of the Andrus Family Fund, one of our long-term visions was to diversify the all-white board. After doing the analysis, I understood that I wouldn’t be able to do that in my first two years there. There were issues of power and legacy, so we had to conquer those by talking about power and talking about legacy. We also had to get people comfortable with disagreeing and talking about opportunity. It ended up taking four years.
I’ll also say that I’ve gotten comfortable with accepting when something just isn’t my fight. Fragility tendencies, that’s not my fight. I can get people support to do that work themselves, but I’m not taking it on. Leaders have to struggle against the tendencies in our souls to fix everything. I’m very comfortable in my leadership to be like, “Can I get you some help?”
We’ve had conversations about what it means to create a culture of care within an organization. Tell me what that means to you.
Leticia Peguero: After the mass shooting in Atlanta, I reached out to the Asian people in my community to see how they were doing. That included someone at Nathan Cummings Foundation. Then I wrote an email to the whole staff to acknowledge what had happened. I got all these personal emails back saying, “Thank you for naming this.” To me, that is a culture of care.
It’s not enough for me to be suffering at the horror of what’s happened in the Asian community and with Daunte Wright. We have to be able to create space to acknowledge that, for all of us, but especially for Black and brown people, this is collective trauma. Leaders need to be able to name the sorrow, sadness, feeling a lack of safety, or having conflicted feelings about police that may exist in their team. They need to be able to give people the space to name that and be in community with each other. And they need to do that without feeling like they have to fix everything.
That’s really hard to do when people have very traditional models of leadership and this notion that they have to talk all the time. I find myself getting trapped in that, too, but lately, I’ve been very aware of what it means to dial back and create the space for other people’s feelings and experiences. Without it, the image that comes to mind is a suffocating environment. Especially for those of us in the social justice space, to not acknowledge the murders and the murder trials that are happening, it actually feels harmful to me.
Often, well-intentioned leaders who haven’t developed those skills can do more harm than good. What have you seen that doesn’t work, but people keep doing it anyway?
Leticia Peguero: Leaders have to think about the boundaries we need to create to be personable, lead a team, and allow people to have confidence in them. It’s important to be attuned to our own need to be liked. Everybody’s read Brené Brown and wants to have vulnerable moments, but an important question for leaders to ask themselves is: What is the intention behind what I’m sharing?
If you have no self-awareness or very little emotional intelligence, you don’t always know your intention. If your answer is for people to feel like you’re their friend, don’t share. These people might be your friends, but they also need you to lead. Oversharing is problematic because it’s not about the other people in the room; it’s about your need for fill-in-the-blank.
I also think there’s this old-fashioned idea that leaders have to know it all, and that is a lie. One, you can’t know it all, but also, people see through it. And the more they see through it, the less confidence they have in your ability to be truthful and honest. They believe less and less in your feedback. Maybe it’s because I grew up in Brooklyn—before Brooklyn was Brooklyn—but my word is my bond. I believe that if you don’t trust that what I’m telling you is honest, or in your best interest, then I don’t belong in this position.
I’ve worked with plenty of people in leadership roles that I didn’t trust as far as I could throw them because they would say something that was only true until the minute you left the room. That is the thing I see people doing over and over again that feels very harmful. Sometimes I wonder if they know that nobody believes what they say. If they do know, and they continue doing that, I don’t know what to tell you. But if they don’t, how might we create the conditions for them to understand that’s how people perceive them? My experience in philanthropy is that oftentimes people just assume that you, me and everybody else is wrong. That is not leadership.
How do you enable people who aren’t in so-called leadership roles to see and claim their power?
Leticia Peguero: There are tools, like setting the agenda for a meeting, and those little things matter. There’s also helping people to manage up by making clear the ways they have and can exercise their power. So, for example, I always tell people that I’m not going to be offended if they have to remind me to do something. And I know this sounds really basic, but how many meetings have you and I been in where no one asks a single open-ended question? Ask people: What do you think? How can you help me shape this idea? How could we do this differently? I’ve had tons of bosses that like never asked an open-ended question.
When someone wants to challenge something or request a salary adjustment or a title change, I tell them to go for it. I tell them to do the research and come back to me with an argument that makes sense. I might not agree with what they argue, but I won’t shut it down, and I will always provide my own research and rationale for why I agree or disagree. We’re on the same team, so let’s get together and have a thoughtful conversation.
Also, let’s have the conversation in a way that helps them to feel good about it. Do they want to have the conversation in person, on a video call, on a call with no video? It’s important to do things in a way that gives the person agency over their time and the request they’re making, especially when it’s a situation where I have the power to say “no” to the request.
These methods make me think about your work as an executive coach. Sometimes, people approach coaching as a corrective action, but you approach it as a transformational practice. Can you tell me about that distinction?
Leticia Peguero: I do think of coaching as transformational. One of the major reasons is that it doesn’t come from a deficit perspective; it comes from the idea that you have what you need. Sometimes, it’s hidden, or it might be a part of you that hasn’t been allowed to speak. This coaching philosophy comes from a place of saying that there’s nothing wrong. There may be things that we have to think through, shift, or make room for—and that framework is, in and of itself, transformational, especially for women and people of color whose whole lives are spent responding to being othered.
What does it mean to believe your body’s signs that you are tired? What can we give ourselves permission to put down? How can we show up for ourselves differently? One of my clients is a brilliant woman who has been organizing her entire workplace, but she had not called what she had been doing “leadership,” which is exactly what it was. So, to me, that’s what the sacred coaching space can be for people. Coaching can allow us to begin to create the sense of personal agency, or what I call “moments of freedom,” that allow someone to make good decisions within the conditions they’re working in. Moments of freedom feel really important to me in a space that can be so tight—moments to breathe, to decide for ourselves, and to have intention.
It can be difficult to work in a field that operates with so little accountability, and under CEOs that have so little self-awareness, and continue to show up with integrity. What are some practices you’ve embraced that keep you grounded in your values—not just as aspirational ideals, but as daily actions?
Leticia Peguero: The first thing is: I’ve named my values. And doing this has helped me to recognize recently that something in me is evolving that hasn’t been here before. I also feel like I don’t believe the hype about this sector at all. I always tell people that when I started working in philanthropy, I would go to these meetings and, all of a sudden, people thought I was super-funny, I had the best shoes, and my hair always looked good. Sometimes my hair did look good, and I accept that I am pretty funny, but it’s important to interrogate whether or not what we’re being told is reality or if it’s just the hype of working in philanthropy. I understand that this is about my having a relationship to power, and that I have to examine that all the time to stay true to my purpose and my values of justice.
If we don’t have some type of self-reflective practice, whatever that may be, philanthropy can be really seductive. It can make you believe things about yourself that aren’t true, and it can blur your relationship to power. It can make you make really poor decisions on behalf of yourself, your team, and the community. We have to be able to admit what is real and what is fantasy. Knowing and naming your values and being able to honestly question your relationship to power is the only thing that will keep you grounded in this space.
