In this episode, we’re joined by the inspiring voices of Alison Overseth, Gisele Castro, and Erica Hamilton at The Women’s Leadership Council. Our discussion centers around the dynamic landscape of leadership, highlighting our personal experiences, insights, and the ever-important journey toward diversity, equity, and inclusion (DEI) efforts.
We’ll dive into topics that are pertinent for any woman pursuing a career in leadership, specifically current and future CEOs and EDs.
Join us as we get answers to the following questions:
- What’s the importance of defining a North Star to guide your decisions and actions?
- How do you maintain and balance your peace and well-being in such a demanding job?
- What mental shifts and practices are necessary for leading an organization?
- What bright spots and challenges will we see as the next generation enters the workforce?
- What are some hard-earned tips for recruiting, managing, and changing your board?
- And how can we drive authentic change through cultural shifts and ongoing DEI efforts?
“[H]ow much are we pursuing excellence and how are we passing on what we have learned to another group of people? […] As an organization that at one point was not so visible and now it is, it comes with different pressure points… I didn’t know I signed up for that. I did, I actually did by being a women leader.” Gisele Castro, CEO of exalt
Important Links:
http://exaltyouth.org
http://www.pasesetter.org
https://www.memoinevergot.com/
Support this podcast: https://anchor.fm/nonprofitlowdown/support
Episode Transcript
RHEA 0:00
Welcome to Nonprofit Lowdown. I’m your host, Rhea Wong. Hey, podcast listeners. Welcome to another episode of Nonprofit Lowdown. Today’s episode is a little bit different than the usual. It actually is a live conversation that I was facilitating with three incredible women, Erica Hamilton. Alison, Overseth and Gisele Castro.
In this conversation, we share the ups, the downs, and the pains of being an executive director and running a nonprofit. I think you’ll really enjoy this conversation, as did I, and stick around afterwards and you can participate in the activity that we do. So let me know what you think. Thank you, all of you for being here.
I am Rhea Wong.
I’d like ambition is to be Asian, Oprah, so making it reality. I’m delighted to interview my friends, my colleagues, my sisters in arms. Yeah. Erica Hamilton, Gisele Castro, and Alison Overseth. I did have a beautiful intro, but I don’t have wifi so y’all are gonna have to introduce yourselves. I know, but if you don’t know, you gotta know.
So let’s start with you Erica.
ERICA 1:21
I’m Erica Hamilton. I am CEO and founder of a small strategic advisory firm called The Memo I Never Got. You can take from that title what you need to I, my background sort of. Motivation for starting that firm was to basically take the wisdom, the trauma, the experience, the insight that I gave working across sectors and in a variety of positions, including being the ED of City or New York for a number of years.
But to take that and to really try to apply it to working with leaders who hold identities that I deeply care about. And I would work with for free if money was no object and I had no bills. Right. And so I’ve been doing the memo I never got for the last few years. Native New York firm live in Brooklyn with two children, about to be an empty nester.
So empty nest in audience looking for advice.
ALISON 2:05
Wait, did you found an interesting group of women who get together regularly? Founder of the women’s leadership?
GISELE 2:17
[00:02:17] Gisele Castro: It is a pleasure. As soon as I walked in, I was like, wow, this is powerful. I could feel the strong energy. I am Gisele Castro, the Executive Director of Exalt. We work with young people who are court system involved, ages 15 through 19. I’ve scaled the organization successfully during political climate, during economic downfall, during the biggest challenges, and we have done extraordinarily well.
And we’re about to launch a new strategic plan, and it’s exciting to be here this afternoon. And over to you, Alison
ALISON 2:50
I’m Alison Overseth, the CEO of the partnership for afterschool education, which I’ve done most of my adult life. So 13 and a half years as c e o, 12 years before that as chair of the board.
And we actually stay relatively the same size, so it’s a different kind of model. So we say nimble and we’re. Small. We have 13 full-time staff, two, two and a half million dollar budget, but with a large footprint. So we work 1600 community based organizations throughout the city to improve opportunities for kids living in poverty.
We’re happily with many of you closely, and I’ve been part of the Women’s Leadership Council for five years, six years anyway, and it’s the best thing ever. And you have all given me such good advice along the way. So anyway, it’s a delight to be here and to see everybody.
RHEA 3:30
We were taking a, about. How we wanted to structure it.
We have 50 minutes. We could talk about a lot of things, but there are two things that we really wanted to come out of today’s conversation. One, how to survive and thrive in this hard-ass job. Two, sharing hard won wisdom. And each of these ladies have individual and unique experiences. So I’m just gonna start off with a fun one, which, and this is for all of you, my best friends know blank about me and not a lot of people do.
ALISON 3:55
I am a total crier. Anything. And actually bizarrely not always at. Sad things. It’s like the happy things, but I weep and get choked up really a lot.
RHEA 4:05
That’s okay. Nice room for emotion here. Elle, what about you?
GISELE 4:08
I’m going to say that my very good friends know that I have a really good sense of humor and I’m always so serious.
So this is why it’s a big deal.
ERICA 4:19
I’m gonna go with. Really good friends know that I’m a creature of habit. Mm-hmm. I, I crave the joy of things that are familiar and so I always get clowned and we go out for what do you order? What do you drink? It’s always the same day.
RHEA 4:39
This is. Spicy question. So Erica talks a lot about your North Star. What do you mean by a North star and how do you use it to both guide your decisions? Mm-hmm. And to check in along the way, because sometimes we can lose our way.
ERICA 4:52
This concept, I often talk about when I’m working with CEOs or EVs or even when I was sitting in that seat, especially in these roles.
I think one thing that we often don’t take the time to do as leaders is to really, before we dive head first into the deep end of the work, is to step back and really take a minute to think about. What is the North Star? What is the actual legacy I am trying to achieve By involving myself in whatever it is I’m about to involve myself in?
Whether I’m running the thing, whether I’m sitting on the board of the thing, what is it that is motivating me to invest time and energy in terms of what I want to achieve? Why I think leadership of this thing is important and for me to own it. And I think it’s really important to define that for yourself and then dive into the pool because it’ll give you a north star to keep you grounded when everyone else around you, including the 12 year olds that work for many of you wanna.
Why what you’re doing is wrong, why all those decades of experience that you have are no longer relevant. And so it just gives you something to really ground onto and then creating space to check in with yourself because that legacy definition will change over time as you learn more, as you evolve. As you grow.
That’s right. But always centering that because it will just. Give you that space and that thing for you to stay centered on. No matter this chaos that’s going on around you may create in terms of imposter syndrome or the doubts that will creep in this thing will give you an anchor to hold onto. In those times of pressure.
RHEA 6:27
Some of us are thinking about succession planning and legacy, so how does the North Star connect to this idea of legacy?
ERICA 6:33
Yeah. The one thing I would say, I think especially sitting in this job and especially holding identity of women, we tend to want to do too much. We tend to wanna do all the things.
Everything we see that’s broken on the landscape, we think is our job to fix it. And there’s something about doing this activity to define legacy that will also hopefully compel you to clarify priorities. And the hardest thing you have to really realize is. Everything that’s broken is not mine to fix.
Yeah, I’ve got to really,
I need to get this one all day, but you’ll really, it’ll help you hope and hopefully you have someone, you have this circle and you have a person that you can go to help you really commit and align, but it’ll help you again figure out what is the work you need to be doing, investing time in so that you are not.
Burning yourself down, grinding yourself out, leaving nothing for anybody around you to get that needs from you in your personal life, and also leaving nothing for yourself to pull from.
RHEA 7:32
Mm-hmm. You said a mouthful? Mm-hmm. All right. Let’s talk about work life balance for a second. Allison, this is for you.
Can you walk us through as someone who’s been at the organization for a long time, Forever. I feel like one year equals seven. How do you maintain and balance your peace and wellbeing? Well being this very Dominican up, and I think you mentioned something about seasonal and understanding the generation that you’re in.
ALISON 7:57
I actually don’t think there’s work life balance. I think there’s work and there’s life and you do one at one time. So it’s finding that tapestry, I guess that works for us in our different ways. I have to say I’m used ’cause I married a board member. Right? So we actually do the work together, we do the personal stuff together and it’s like we are an expensive couple to go out to dinner with.
Near my benefit, I’m just saying seriously, a lot of the people I care about most, many of whom are in this room, but others in my life. Very much care about what I do at work. It’s if you actually at some level don’t care about other people’s kids, it’s less likely we had things in common, and that’s both personal and professional.
Some of those things overlap in different sorts of ways that I find really fascinating and good and helpful. What we are talking about generationally is. So I’m 64, my kids, my baby is now 27. That’s freaking me out. And on a second marriage, a good marriage which, so we can talk about the experience of the bad marriage because I couldn’t have done the things I’m doing now with that person and I can do different things now.
And so all those things. But I also know, ’cause we a number of adults in really different places and like I looked with the young women who were on my team who had young kids at home during. Covid, there’s less things you can take on. I’ve had two of our staff have been going through the I E P process with their kids with special needs.
It’s really complicated and I think that we often don’t give ourselves enough grace to just say where we are in life and to recognize that these are not nice to haves. These are critical to who we are, but recognizing that there are different times and different places for what you can do and what you might want to do depending on everything else that’s going on.
I. Remember being in a job that was really nine to five when my mother was dying. Mm-hmm. And that was really important to me. Mm-hmm. I was able to spend time with her because it was not that all consuming sense of things. No. And I think we don’t talk enough about that. We know women take on disproportionate amounts of.
The personal care anyway, but I think that there’s a, in fact, I’m delighted right now. There’s a woman who was working with us when I first started at Payson. She, her son was eight and she’s got no interest in being an executive director. I’m good at this, but I never wanna be an executive director. Now he’s in high school and she’s looking at executive director jobs, and now’s her time for that.
But it wasn’t before. Yeah. And so I think as we imagine our capacity to do things both personally and professionally, we have to think about that. And there are a lot of systems that could be a whole lot better in terms of childcare and everything else that could support us, but it’s also pretty personal, right?
And if there’s a special something going on in life, I think we have to appreciate that. And I will also just say, It’s really nice to have love in your life. It’s like really nice to have relationships you care about and it’s really nice to spend the time that needs to be there for that. And that’s important.
And then I’ll just finish with my other work life balance. It’s coming from a retreat we had some time ago. I will say Hot B Bath every single night. I just need that time. I just need that.
RHEA 10:56
Ms. Elle, this is a two-parter for you. Hey, go for it. For those of you who don’t know, exalt has been on a rocket ship, so I think Giselle, when you started it was like under 500 K and then it is what, 6 million now?
Eight. Hello? Yeah. Okay, so talk to us about, As a leader of the, I don’t even wanna say, fast growing, just like exponentially growing organization. What mental shifts and practices have you had to make internally to be able to lead this organization?
GISELE 11:30
I love this question so much and thank you, because I live it and I breathe it and it starts with, The why, like knowing why do you want to take on a massive challenge?
And for me it’s the juvenile criminal justice system in New York and abroad. My story is that I wanted to become a journalist. I believed that I was gonna travel the world and be on media with you. Uh, but then my older brother was impacted by. The system and he got out of it. And this is how I met Allison when I decided, let me go back and rethink my career and went to Bank Street and my nephew was in Florida, arrested and sentenced to 10 years of prison, and he was 18.
At that point in time, I understood with absolute utter clarity, I must do everything possible to dismantle this system. And what that is to me is that the US is still number one in mass incarceration. And that to think very clearly about system change, it means moving so many people forward. So then there goes this.
Story of creating a design, a concept, which is an ideology, it’s a framework. Then really thinking about all the people that will be invested, and it starts with your staff is also looking at the governing body. It is all the people who will play a role in philanthropy. It is an internship sectors, and then it is understanding systems.
And for us, one of the biggest systems was creating a court advocacy model where we had first the das in Manhattan. In Queens and in Brooklyn, reduced sentencing, and these were serious felony offenses. When I get to see the data points in so many ways, that is in dollars and cents from, it was a $900,000 budget with a $400,000 deficit.
What that said to me was that a lot of people will quickly say no to our young people, and what I understood. Stood was that I was always so proximate to the issue. And when we understand these big questions of life, it is at a certain point it is that what fuels purpose. And I think that a lot of times we are always thinking about what drives us.
And then at the core, what are we so afraid of? What are we deeply afraid of? What I was afraid of Ria? Yeah. Was I believe that I would fail until I understood wholeheartedly. The system, society, America has failed so many people. Mm-hmm. So it was my perspective that I said I will not participate and I will not perpetuate a cycle.
I will think very clearly how I would move something forward. So then when I understood that I would get a lot of noss, I source an opportunity to convert people, for people to really understand that at this moment in time, the climate has not changed for any one of us. I would say that then the levers that I pull are the court system, the education system, philanthropy, the young people themselves, and more specifically is myself.
And I’m gonna close that with this one At night, I have to close my eyes. I put my oils, the doTERRA Lavender Council, my chest, and I just sit in my lovely bed that I barely get to enjoy, and I pop my pillows. And I understand that I have to breathe from deep inside what I call my chakra, my deep level, and always ask myself this massive question.
How am I today? What has scared me? And when I wake up, How am I gonna do this again? And that is the most intimate conversation that you have with yourself when you understand that you’re driving change. I understood this other thing. I did say I was gonna stop it and here I am because I’m gonna be 50 and in three weeks and it’s like, woo.
And I understood a lot that you pay a price, right? That you pay a price. While I was leading the organization, I have fire surgery and I also understood. Stood what happened at my last surgery when I was going to the, or when I was being rushed in, and I said, today was my last day. It would have been enough.
And at that point, that is when I began to understand, I am glad that I took on such a concept that is difficult. And I think that is what it is. When you understand who you are and what fuels you and what scares you really, truly frightens you go ahead and confront it because it is only you that you’re dealing with to move people forward.
RHEA 16:18
You spoke about levers. Yes. One of the levers being staffed. This question is for Ms. Erica. Mm-hmm. Let’s talk. Let’s talk about the babies who work for us, the Gen Zs and millennials, I have feelings about that, but they are more vocal than ever for the Gen Z. This is the first generation that’s entering the workforce without having had a job before entering the workforce.
So, question for you. What bright spots do you see and what challenges do you see? I try to start optimistic.
ERICA 16:51
Yeah. I think, and again, I. Channel it through my experience and the experience of leaders I work with now on the bright spots. It is interesting. There are quite a few folks I’m working with now who are going through this moment of having to rethink their organization structure because of some physical pressure.
Right. And a client recently had a meeting and it was energetic. I’ll say that on Zoom. And one thing I said to the client when we finished, I said, I first wanna take a minute to be grateful for some of the blessings of that meeting. And they were like, what? What? Seriously in this zoo? And you know, I said to them, I said, listen, the first thing I’ll say to you is, which is do your question.
People were engaged, like the people were asking questions, really trying to understand the why behind things. They weren’t necessarily throwing up. I, we can do it better, but there was a lot of curiosity and inquisition and I said, when you’re going through these moments, one thing that you never wanna see is silence.
Or disengagement. And so to that end, I will say, especially in this moment, I am seeing a lot of hope in terms of these groups of people are trying to channel their energy into trying to figure out how to be a part of the solution and part of what we need to do on the leadership side and speak out.
Constructive ways that we can create for them to distribute some of that energy. And also, quite frankly, for them to get a little bit more visibility into the complexity of the situations that we’re dealing with. Everything isn’t just a, oh, you didn’t think of this moment from a younger person to a older leader.
I will say I still see that energy. I see that enthusiasm. I think trying to figure out as leaders, how can we continue to try to pivot it into being used in constructive ways. I think also thinking about how do we disabuse folks in that generation from what I think is this lens that they walk into many situations with thinking I could do that better with no basis, no like, Data or experiential basis to say that.
And so how do we create pilots or spaces where they can feel heard, right? But we can also help educate them on this is the full detail of a situation that we might not have exposed to the whole staff, but we’re gonna share with this committee for them to understand and we want your input. The times where I’ve seen that happen, I have seen a lot of instances where you will inevitably get those generations of people to realize, oh, this is harder than I thought.
And not that the world of work should be about teaching them, but to the point you just raised with that stat. As leaders, when you’re bringing these generations in, like unfortunately the work does become about teaching them. Yes. More about how to lead, how to show up. My favorite thing to talk with leaders about is really teaching staff about the moments in leadership when there will be no winning solution.
Like literally, I have a menu of shit to mix. Mm-hmm. An A is dark colored B is like, sorry if anybody, I’m not a propan person. But disusing, again, these generations of thinking, there’s a winning solution and you just didn’t know how to get to it. Sometimes there isn’t a solution that’s gonna create a win for everybody, and so we have to pick the least a traumatic option and it means somebody’s gonna lose.
So it is how are we creating those constructs for them? How are we taking the one person or the two people you might find in your organization who are part of those generations who are phenomenal? I don’t know if you ever come across these people where you’re like, oh my God. How, how do you think this way?
Why do you think this way? It’s so different than your generation. And how do we engage them in the process of speaking to their people and helping to translate? So it is not just us talking heads, trying to convince these generations how to think differently or the way that they’re way they operate needs to change.
So not doing it alone is the other thing. Like how do we enlist them in pause in a way that’s productive.
RHEA 20:46
I’m gonna ask about the board. It can be complicated, right? They can be a sale or they can be an anchor. Allison, I’m gonna start with you because you not only lead your P Board, but you also lead the Smith College Board, so that’s a very high caliber, high octane group.
Anything that you feel like you can share as far as hard ones hits on recruiting, managing, and changing the board.
ALISON 21:10
Bravo for making it two weeks.
RHEA 11:34
We could spend hours on this, but I think when starting at the beginning, Is the best chance to have a functional relationship and a healthy relationship on a board starts before their board members.
So it really is being clear for everybody on why this person, what you need. I’m the C E O. You are a board member. You are important, but so am I. And we have very different roles. If we’re successful, you are doing what you do really well, and I’m doing what I do really well. And a lot of that is going to be mutually supportive to have good things happen for kids in New York City in this case.
And I think that those earliest relationships cannot be underestimated. I had a board member suggest somebody the other day that he thinks should be on our board at pace, so I meet with him. He seemed nice enough, he had. No good questions. Invite to our benefit as a guest, not a thank you note, not a suggestion.
No enthusiasm. I just don’t get it. What do you think this rule anyway, and? Telling my board member, I don’t, I just don’t think that vibe is happening here and recognizing what we need as an organization. So there are times when you’re 500,000, you need something else at 8 million. There’s just different levels of sophistication and what you need.
But really assessing that on a regular basis at pace. We have never had a give or get nor term limits. And one, because from the get go wanted to be able to have economic diversity on the board. Mm-hmm. And managing the board I think is really important. I’ve had chairs who are really good at doing that and chairs who are less good at doing that.
And then it falls to me, which is just annoying. Mm-hmm. But managing the board, it’s gotta happen every year. Even if your term’s not up, you should expect to hear from someone on the board if you haven’t attended many meetings, or if you have not gone to a program, or if you have not brought friends to the benefit.
Just holding those standards in place on a regular basis. I think that we all know this. It’s not, I’m not saying anything magical here, but staying on it matters because then it can be really functional and what you’re talking about with the, uh, with the younger people on our teams, if we can lift up the board members who really get this and do it well and try and move them to leadership positions, then you’re modeling the behavior as opposed to yelling at the people who aren’t getting it done.
I have found time and again that if we’ve got that modeled behavior, everyone else rises to it. And I love occasionally bringing, we’re bringing two new board members right now, and they’re both coming from very different perspectives, very excited. But I can see already some of the past board members are raising their game because they’re seeing it and they’re watching it.
I as both as the chair of the board at Smith and c e o at Pace, we think of our boards as this. Big, annoying, time consuming thing, and I just can’t say it’s enough. We have to have individual relationships with each and every one of them, and it just makes such a difference. Best when we could do it in person, but even if it’s over zoom, where I’m like literally looking you in the eye saying, you’re gonna chair that committee.
This is how we’re gonna stay in touch. This is what I hope. Give me feedback when you need something. Those things, we create a contract with each person in that own set of ways. Mm-hmm. And that you set the expectations high of what you need. And as the final thing I’ll say in both roles, I just really encourage feedback so when somebody does ’cause in all of our roles, we can be intimidating, I think, but really say no.
If you tell me I’m listening to you, I’m gonna do it differently next time. And you do well. You just build that trust of your leadership in either position. Mm-hmm. But also that you have a relationship with them that is mutually respectful, that you’ve actually listened and that. You’re gonna make change when you think change makes sense.
And so all of those pieces come together. We can talk about firing board members if you want to, ’cause I’ve had that experience too.
ALISON 24:52
Yes. One of the things that has to go with both staff and board and all of these different relationships we’ve had, and I’ve struggled with a number of different things as we all have through the years, and my husband finally put it perfectly one night, he finally just said, you’re expecting things of people they’re not capable of doing.
Some things need to be broken. They can stay broke. We can’t. Do that. And there are times where that really resonates with me, and we find that on staff. You’re like, but you could do this, but they can’t.
RHEA 25:16
Giselle, I know you’re in the middle of revamping your board right now. Yeah. Mm-hmm. Tell us a little bit about what is happening for you. Any lessons learned?
GISELE 25:22
I would say that it is part of a strategy. It’s a long-term relationship. They are assessing you as the leader, your work, your project, your success. Because when I started to think about diversifying my board, These are people who I envision that they will then set the course when the organization is in 2030, and also are the ones who are going to be responsible for a succession plan.
And also there are the people who they represent for us. We just brought in Dr. Vez. We brought in, yeah, the commissioner from the Department of Probation, former Anna Bermuda. We brought in a senior person from Deloitte and we brought in so many other great thinkers and I had to sit down with my coach and I did this work, which was, what is this new profile of group of people?
Anticipating what could be potential wins and also challenges because the wins of the core board is not the wins of this current board. These are board members that they know how to handle a lot of challenges and a lot of the work has been making sure that they could really identify and define their why.
I’m going to close that with this one ’cause I think that this was the unifier. Within our organization, when we onboard people, they have a few readings. Michelle Alexander, the New Jim Crow, Paulo Fairy, the pedagogy of the oppress, right? Brian Stevenson. Just Mercy, and whether someone has read it or not, but it’s like it’s grounding everyone.
But then more importantly, keeping them at a high level on what is governance policies. Fundraising fiduciary responsibility and then very quickly giving them a win. The person who leads Deloitte, she will be with 20 of her staff on Friday. In the organization launching a volunteer program. Then the next one on Wednesday we have our gala will be standing up on stage making the final fundraising appeal.
So it is raising the standard and giving them a win that’s visible. The other thing is that I started to diversify the board in terms of race. The first process was a challenge. The board was not ready. The second one, I think that the board is ready, but I think that at this point there’s going to be massive changes.
I guess that is something that I am anticipating that when we’re thinking about systems design change, what are some of the great opportunities that we will get to see that hopefully we. Model and share our lessons learned. A lot of them good. And then a lot of them big challenges. Yeah.
RHEA 28:14
You have a coach, and I think we all need to recognize that people need coaches.
You’re not just born knowing how to be an ed. We wouldn’t ask Serena Williams to step onto a tennis court without a coach. So I think that’s one thing that. We should really be advocating for. I wanna talk about changing the culture of boards. And Erica, do you want this question, particularly as it pertains to d e I?
Because I think obviously post pandemic, post George Floyd, post B l M, all of these boards, which were very white. We’re sitting there being like, oh, we have to do a thing now. We care about d e I now. Mm-hmm. And so I think there was a big rush to train people in d e I. All of a sudden, I don’t know how effective those efforts have been.
So how do you think about leading a board through. Real change as it pertains to D E I issues and how It’s a verb, not a checkbox.
ERICA 29:08
I think one of the most important things to start with is the c e o can’t be the person leading all that work on their back. They can’t do it for the staff and the board and the funders.
It’s like ridiculous. The first. Step, I think is even ascertaining. Where is this board in terms of their ability to have someone on it, also step up to lead it, to guide it to be spokesperson in terms of belief and commitment, which is what a lot of organizations have tried to do and are still trying to do.
I think it’s impossible to go from. We’ve done nothing, like the board has never even uttered this topic, except when the staff brings it into the room. From that to now we’re gonna, we’re gonna be like a hella woke and a board. We’re allies now. We’re all allies. And so I do think first, and this is back to the c e o, really being honest about where they are, where the board is.
I think it’s starting to work with the board, like having a conversation about. The journey the board is gonna need to go on, and if the board is not in a place where they’re able to do it. I think also recognizing that part of the work that needs to be done is helping to recruit four people into that board so that the CEO isn’t carrying it alone.
And then I think it is about bringing in, because I have not really ever seen this done successfully unless you have a sitting people and equity officer on your team. I think it’s then hiring the help that you need to facilitate these conversations. One of the things that makes me so sad when I hear it is when I will have a c e O of color come to me.
And tell me that the expectation they’ve got from the board is that they’re now gonna lead d e I work. And I’m just like, what the what? What is happening? And that means creating a budget for that work, like investing in it to the degree that you need to. It means also doing real diligence to hire people who are trained and experienced.
Not just who say they are and hold certain identities ’cause that’s a disaster to do cleanup on aisle five after it’s done. And I also think something that’s powerful that enough boards don’t take advantage of and CEOs is use the network to figure out whose board has done this or is doing it. Can I lean on you and maybe bring you c e o in and your board chair to come and talk to my board about examples of how this can be done.
I think boards often hear best from other board members, as stupid as that is, and it’s exhausting. As a C E O, especially of a nonprofit, if you don’t have somebody on your board who can speak to the board and you have to do that work, you’re carrying the wrong weight. That’s not the work you should be doing and the windows closing.
As with all things, I think we have these flashpoint moments, and then the way I think about it is literally, it’s like somebody just started a stopwatch. And it’s like, everybody better engage on this topic as quickly as they can get all the funding you can because with every minute that passes, this is what’s happening.
It’s like the mission impossible, dynamite fuse, and it’s gonna shut and be done. And so it feels like we’re in that moment, especially as we head into the election and all the foolishness that’s about to start.
RHEA 31:58
Let’s talk about fundraising.
My favorite topic, as we know, obviously having relationships with funders is a key part of your job.
I would say probably the most important part of your job. I think we can go down the list of the million ways in which we’ve had dysfunctional relationships with funders, but let’s keep it positive and we’ll start. Allison, actually, this will be for all three of you. Can you walk us through a story about a funder that felt like a true partnership?
ALISON 32:26
It’s about relationships, and that comes first, but I think that’s true in fundraising, individuals and institutions, right? Mm-hmm. It’s do we see eye to eye? Do we have things we care about that are the same? Do we have something we can work on together formally or informally? I feel it that way on a lot of levels, I have to say.
’cause after we were talking the other day about this, Rhea, we don’t have any funders anymore who are in the kiss the ring area. It’s like I, life is just too short. I’m really willing to work hard on our mission and make sure that all the things are happening. But the sucking up thing I just don’t have time for and.
Now, I haven’t been in the position where somebody’s saying, here’s $4 billion and if you suck up, you could get it. ’cause that might be different. But part of what I’m really taken with, and I have to say, I think of a billion, billions, it’s expensive. But what I’m taken with is that what the real cost of raising money is.
And in part because we now have funded by Robert Stern Clark, I don’t know if any of you are Philly. Mm-hmm. Awesome. Trust-based philanthropy. Mm-hmm. And what it means is that my proposal to him is making a copy of a proposal I gave to another funder and my reports to him is an hour and a half conversation where we just chat, which is basically free consulting for us.
Mm-hmm. Smart, capable supports us in a zillion different ways, but when I literally think about the economics of. That, let’s say it’s $50,000 grant is worth a 75 or $80,000 grant from anybody else. It’s like all the paperwork, all the annoyance, all the worry, all the concern, all the planning, all the things.
And so when I say that I have less of these funders that require a ton of that because. That money’s very expensive to get. Mm-hmm. If you’re having to spend all that time making them feel better about themselves, it’s expensive to us, and I remember when I first got to Pace, we had a couple of $5,000 grant makers.
I’m like, we’re spending $10,000 to get 5,000. We’re not applying for those anymore. We’re done with that. And anyway, so it really is a cost issue, but there are real partners out there and they’re introducing you to other people. They’re putting a good word when you’re not in the room to other funders, they’re creatively saying, oh my God, have you met these people?
You guys could have a fun partnership. Not telling you you have to, but introducing you to people and resources. And thoughts, and that’s really powerful. And then we’re doing the work together.
RHEA 34:34
And something you mentioned about costs. It’s not just the cost of what it takes to administer the ground, but the emotional cost.
ALISON 34:41
it’s just exhausting. Exhausting. They make you feel crappy about yourself. There’s a lot of reasons I should feel crappy about myself, but not because some funder thinks I should feel crappy by myself.
RHEA 34:51
If there are any funders that make you feel like your soul pigs suck about your eyeballs, you gotta go.
GISELE 34:54
I think that. Now that I think I know, ’cause I lived it, I have said no to funders because the work itself is that difficult and that challenging. And it is a relationship and I agree with you that it is a, call it trust philanthropy. And I remember with one funder that started off with us at $75,000.
A year. It took a while, but this person had to travel, sit with me, have lunch, observe a class, go into a courtroom, go into the school. But they were really learning and that’s when they knew it was like, this is a good partner. Mm-hmm. This is someone who was going back and thinking through. Who are the other people that Exalt should be introduced to?
And long story short, after Covid when I developed like another strategy, he says, this is remarkable. I’m gonna fly in, spend more time with you. And the same process occurred brought in his entire trustee, and I had. A proposal of $2 million and within an hour they approved it. Oh, that’s yay. Yeah. And then from there, it’s now how can we support an education and a national framework?
So I, I would say that because it was intentional, deliberate, and slow. At the point in time that we’re gonna scale for a bigger impact. They know what we are able to offer. And I also think that they began to see like what are our challenges and how can they either meet those gaps or introduce us to other people?
And it has been wonderful because. It’s the perfect model, right? It’s like the perfect model of having someone who could start with a small, that’s not a small grant, but could start with that level of grant and then think through long term, which is sustainability for an organization.
RHEA 36:44
And I think to add to your point, when we are operating from a place of fear and scarcity, we say yes to money, we probably shouldn’t because we believe that no more is going to come.
Yes. And instead, if we’re actually able to, to your point, stand so strongly or. Our belief system and our value system and say no to money, that does not align. We say yes to other money.
ERICA 37:06
Oh yes you do. So I’m just gonna ground that thought in a different perspective, which is sometimes you gotta say yes to that money that you’re like, I really don’t want, because you might not have the benefit of the surplus or other funders to go to.
So there’s a reality to this. I agree with everything that has been said, but I also just wanna acknowledge. Fact that sometimes even your, no, maybe you’re accepting the money now and in your mind in two years I have not taken this damn money from you. Yeah. I just wanna Yes, agree sort that bit. The other thing I’ll just say that I increasingly see, especially in the seed I sit in now, ’cause I work a lot with foundations and grant makers, So this game is, it is about impact, but it’s also about nepotism and relationships, right?
Oh, yes. There is so much power in a funder going to another funder, more so than us going to funders. It is mind blowing when you see it, and sometimes you see speed, like you talked about. You were able to do it in an hour. I’ve seen that happen between two funders and six and seven digit gifts on a one hour zoom where I’m like, Wait a minute, did you just get that other funder to match your million dollar gift?
What just happened? And so I say that to say, I think one thing I would definitely encourage us all to do more is for the funders that you have identified who you think of as partners. Like these are people actually I trust. Not only do I respect how they grant it, but I’ve come to actually really like these people.
He is reaching out to ask for help more than we do now. I find so many funders are literally not all of ’em, but so many of them are literally in a space of, okay, what can we do beyond the check? So they have the desire, but they don’t have the clarity on the need, and they don’t have the short list of who should I focus on?
And so by asking, and at least like you’re not asking in a way where you’re dependent, but you’re at least planning a scene in their minds. Of here are some things we’re working on that we might be having trouble with, whether it’s connecting to a specific funder or specific initiatives you’re trying to invest even outside.
One thing I’ll say that’s been interesting is sometimes even outside grant making priorities, so I’ve seen funders like get really excited going back to succession planning when a leader tells them, I think my time is up. And I think I got one more year in the seat. I’ve seen funders step up and be like, okay, you need a grant for a search firm, you need a grant for a coach for transition.
That’s not part of your mission statement, but somehow funds are available. But I just wanna put that out there just as a reiteration, like I think one of the best quotes I’ve ever heard from a woman leader like 20 years ago was just don’t ask. Don’t get. So my idea in life is, It’s not my job to say no to myself.
If you’re somebody I trust, I’m gonna at least make the ask. The worst thing you’re gonna say is, no, that’s not too bad.
RHEA 39:50
Let’s talk about the role that you play relative to the larger community. And so I think the job of an E D R C O is really freaking hard, and there’s so much that not only are you doing, but so many expectations are put on you by other people, whether it’s your board, whether it’s voters, whether it’s the community.
So I guess the question is how do you. Build onto yourself when a narrative isn’t your narrative. Is this a possible task?
GISELE 40:16
Yes and no. It’s understanding life cycles, that this is like a temporary, hopefully, process that you are in this role. Knowing that you’re going to change and to shift and to evolve.
I was experiencing this not too long ago when I was able to recognize, wow, I grew this organization and we’re gonna go through this process again, and then the expectations are higher. Something else that I began to experience early on. I remember when it was recognized that I was the first Latina running a juvenile justice organization.
The pressure that I had that you just can’t fail. When I was like the first woman of color leading, I didn’t know that was a pressure point and a real one that I was representing so many people I never knew that I was representing. And then now that I get to see so many women of color leading. I think that the responsibility becomes, it feels like different, and these are expectations that no point are written in your job description.
At no point do you know what you really are walking into, and I will start to transition with this. It’s this deep question. It’s like how much are we pursuing excellence and how are we passing on what we have learned to another group of people? Your question wasn’t that, but I think that as an organization that one point was not so visible and now it is.
It comes with different pressure points that, you know, like once somebody was like, oh, I didn’t know I signed up for that. Oh, I did. I actually did. By being a woman leader.
ALISON 41:59
I’m gonna go back to actually Erica’s North Star I, my why is really clear in my mind. Mm-hmm. And at some point that becomes my superpower because there’s all this noise around you and other people say, but you should do this, or You’re good at that.
Thank you. Or maybe, but it’s gotta really sit here and when I’m clear on that, I’m good. It’s, it might be a yes, it might be a no, but it’s. Is it makes sense. So for example, it matters to me that I have younger people on my team that I hope are actually developing into awesome people and awesome professionals.
So that word here and there, that way to include them in a meeting, they have no business being in all of those other things. It’s like that’s not gonna show up in pace metrics. But it’s an extension of youth development at some level. But that matters to me. It actually, I think that’s important. I got a zillion mentees and I love that.
It’s not in my job description, but I feel like it strengthens the community and it’s good. And I guess I’ve gone through all those phases, like I need to say no more often. And you know what? I keep coming back. I love, yes, this is cool. I got so much to learn, and there’s all these amazing people out there.
I always learn something and I’ve met somebody new and that really powers me, which actually is bizarrely. Selfish. I go back to there’s a lot of people who wanna define what your success looks like, and I think coming back to how you see it is really powerful. The one other thing I would say, I don’t think we talk enough about that, and I say this to this group ’cause.
This is why we’re all actually here. This is a very generous group and I think that part of being a great leader is being generous. It comes back to you so many zillions of times, and part of the reason I’ve talked to Eric about this since I first got involved, you’re like, this is so awesome. The number of times that one of you has stepped up to say, yeah, I can help on that, or I do know the perfect person for this or that, I consider this somewhat uniquely.
Women centered actually. That idea that if I give, it’ll strengthen all of us. And if we’re strengthening all of us, we’re strengthening me and my purpose, that builds something really powerful. So that whole idea of working with community is not a, it’s just not a burden. It’s the community is what’s fulfilling and is allowed to lift up and help me be successful in the ways that I think I can be successful.
ERICA 44:03
The way I try to think of it as in my leadership, my ultimate goal is to never have regrets. About how I’ve led. I can make mistakes. I’m not brilliant, I don’t know everything, whatever, but to never have a moment where with the set of information I had in front of me. I chose the decision that didn’t reflect the legacy I’m trying to build and the values I hold.
Even if I’m the only one holding that point of view on how we should move, I can’t have the regret. So that’s number one. The second thing that’s important for me, and it is personified in this group, which is so beautiful, is I’m a creature who I crave the comfort of community, so, The thing I say to people is I’m a person.
I always keep gales to my Oprah, meaning I, I’m a pretty strong personality in terms of, and especially as a black woman, the package I come in, people don’t always feel comfortable being direct or being like, Girl, that idea, not good idea. Not good. And so when I find those people who do that and like Lisa Holton, Melissa sitting on this couch, or a couple of examples, but when I find people who do that, I tend to keep them close.
’cause in those moments when I’m like super clear, I still wanna have a space I can go where even people like this community represents to just sanity check myself and make sure that my Oprah moment is not making me blind or deaf to something that I should be missing. And so that’s the other thing I’ll just say.
If you’re that person who benefit from getting opinions from people you trust, Make sure you keep those people close and reach out often. ’cause often it’ll certify what you’re gonna do and make you more confident and also able to withstand whatever happens as a result of whatever it is you do or the decision you make, and not in a way that makes you stand in the sense of failure.
Or extreme doubt of imposter. It’s like, okay, I made a mistake. I’m gonna learn from that and I gotta keep going. Pick yourself up faster.
RHEA 46:01
so much wisdom. Ladies, all last question in the last two minutes that we have. Yes. Okay. What is the. One thing that you wish you had known before you took on this job?
ERICA 46:11
Yeah. Everything that’s broken or every gap that exists is not mine to fill.
RHEA 46:17
I’m gonna add my, not my circus, not my monkeys.
GISELE 46:20
The being told no, like someone saying no to me. It’s okay.
ALISON 46:24
Yeah. It turns out I’m thought a risk taker, which I didn’t think I was, and assessing my own sense of risk and then pulling my team in to be like, this is not a risk if I ask you to do this.
It doesn’t work out. It’s on me. It’s on, and I’m good with. That I’m so happy being wrong and I’ve learned something and it’s amazing. I didn’t know that was a thing until I got some things wrong, but I also realized how powerful it’s in the leadership role to take other people’s risk aversion away, something to hold them back.
RHEA 46:54
Ladies, thank you so much for everything. Thank you. Thank you. We have a little activity te for you. What we would like to do is for you to pot up and say three or four. There are three questions we’d love for you to answer. Number one, what is one big takeaway for you? Number two, actually, I’m just gonna give you two.
What’s one takeaway and then. The second is what’s one thing you might try to do differently as a result of this conversation? Sound good?
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