Passion with Purpose with Gaby King Morse

Join Erin Cox as she flies solo on this episode of Lead and Live Well with guest Gaby King Morse, an influential leader with over 25 years of experience in the non-profit and for-profit sectors. Gaby, now the President and CEO of the Center for Women in Enterprise, discusses pivotal moments in her career, from working in her family's business, to figuring out how to fundraise when the moment required it, to becoming a powerhouse fundraiser and organizational leader. Gaby’s insights into effective leadership, building trust within teams, and the importance of clear and kind communication are sure to make you think, and Gaby and Erin’s stories of the time they shared at uAspire just may make you belly laugh. This episode is not to be missed! 

Hosted by Erin Cox and M. Scott Knox
Edited and Produced by Stephanie Cohen

Chapters

• 0:00 Introduction to the Lead and Live Well Podcast
• 0:52 Meet Gaby King Morse
• 4:02 Early Career and Family Business Challenges
• 5:44 Learning from Family Business Dynamics
• 9:00 Transitioning to Nonprofit Leadership
• 14:40 Discovering Fundraising and Strategic Growth
• 28:18 Lessons from uAspire and Leading Larger Organizations
• 32:52 Joining the Center for Women in Enterprise
• 34:53 Building Trust and Shifting Culture
• 37:17 Leadership Challenges and Breakthroughs
• 39:30 The Importance of Clear Communication
• 50:01 Advice and Professional Development
• 1:04:30 How to Connect with Gaby and Closing Thoughts

Transcript

Erin: Welcome to the Lead and Live Well podcast. My name is Erin Cox, and I'm thrilled to be here with my co host Scott Knox on the Lead and Live Well podcast. We sit down with leaders in the social impact world to learn about their leadership journeys. We talk about their strengths and passions, the transitions they have made in their career, and how they have crafted their own paths to leadership.

Our goal is to highlight a diverse array of leaders and journeys, so that our listeners learn from relatable and compelling examples of what it means to lead and live well. 

So today, folks, I'm flying solo. Scott won't be joining us, but I'll do my best to keep the energy up and the learning flowing. And I know my guest today will help with that because she is full of wisdom and energy. We are all in for a treat today because we have the distinct pleasure of talking with Gaby King Morse, President and CEO of the Center for Women in Enterprise. Hi Gaby!

Gaby: Hey! Good to see you, Erin. It's great to be here.

Erin: Thank you so much for being here. Let me take a moment to just make sure I introduce you properly because we've known each other for years and then we'll dive into what I know is going to be a super fun conversation.

Listeners, Gaby came to the Center for Women in Enterprise in 2019 with over 25 years of experience serving as the visionary leader of both nonprofit and for profit organizations. Gaby has focused her professional life on working for impactful social enterprises, including Discovering Justice, City Year, Crossroads for Kids, uAspire, and now CWE. That is quite a list of organizations. We're going to dive into those. During her nine year tenure at uAspire, she worked with some of the most amazing people to be named later. She was part of a leadership team that built the organization to become a national expert in college affordability, enabling low income students and families to realize the promise of affordable higher education.

At CWE, Gaby and the staff are increasing success for women entrepreneurs from underserved communities through training and technical assistance, research, and the sharing of best practice. Additionally, CWE provides WBENC.

Gaby: Yeah. It's WeBank. It's WeBank certification for women owned businesses.

Erin: Awesome. And actively connects women owned businesses across New England with corporate and municipal procurement opportunities. Gaby is wise. She is fun. She's one of the best networkers I've ever seen and we are going to have a great time today. Welcome, Gaby. Thank you so much for being here.

Gaby: Hey, thanks, Erin. That was a wonderful introduction.

Erin: Well, you're a wonderful person. So that's fitting. So listeners, if you have, you haven't figured it out, Gaby and I, we knew each other before uAspire, but we had the opportunity to be leaders within uAspire. Gaby was the third member of what was then a three person leadership team.

Gaby: That's right.

Erin: That was a good time. That came in to run our development/ marketing/ communications efforts and, and really helped the organization realize new heights. So we'll certainly reference some of those experiences; good, bad, and ugly and beautiful, I suppose. But before we dive into all of that, because that comes a little bit later in your career journey, I'd love for you to just kind of ground us in the steps you've taken.

And you've worked at such an incredible set of organizations in a number of different capacities. So talk us through your career journey and, you know, when, when possible, help us understand in terms of the choices that you made along the way, what came about because of choices you made and maybe what was more due to chance.

Gaby: Yeah, that's such a great question. And I think something that everyone who starts their career needs to know is that it's almost, I don't think I know anyone who sort of laid out their trajectory and that's exactly what they did. So my first real job out of college was at a nonprofit.

It was a research education nonprofit, and I had a job that I think when I look back at it, set me up for this job, set me up for being a CEO. And that opportunity was that I was the admin, the executive support of the CEO of an organization called TERC in Cambridge. And so immediately, right, I was the young whippersnapper who, you know, I was excited to sort of be in the middle of it all. And ready to do whatever the CEO needed to support him to move forward. And it's just, you know, there's so many moments now as a CEO that I can connect all the way back to that. First job. 

Erin: I love that.

Gaby: I think a CEO or anyone who is an executive director, you really have to be sort of a generalist in a way, but you need to bring something specific to the table.

So you kind of, you know, you can't just be a generalist, at least with a small nonprofit. You can't just be a generalist, but you need to at least have a strong knowledge of the other pieces and how they all come together, right? So you might be a great fundraiser, but you better be ready to be the finance person if that's necessary, right?

So, that really set me up in a beautiful way. And then a lot of things happened before I actually then was not in a nonprofit and I worked in some for profit situations, but the one that really resonates and I'll talk about is that I actually worked for my family business. I worked for my mother and my grandmother.

And it was actually, my great grandfather launched a business and ran a summer camp up in Maine Julius Bloom launched Camp Fernwood and I was Third, let's see, one, two, three, fourth generation of that family business. And it was a beautiful business. And, you know, as Erin said, I, I do like, I do have a lot of energy.

I like the goof of camp. I love kids. I love working in teams, all that stuff. So in many, many ways, it was a perfect role. And I enjoyed it tremendously. The thing that was tough for me was really the family business dynamic. And anyone who's in a family business knows how important it is to, to dive into that full force forward and talk about it.

Make sure that everyone has a really clear understanding of roles and development, all of those things. And I think at the time that just was not that wasn't in place, you know, I love my mother, I love my grandmother, but that kind of clarity for the business was not in place. And I thought, you know what?

I love this work, but I don't love the management structure and how I feel within it, you know, because it's just, it's complex, right? So that could be a whole nother podcast. But when I talk to other people in family businesses, they are very similar, it's not, it's not unique. But the ones that really do well in family businesses usually have an outside consultant helping with those kinds of dynamics.

We didn't have that. So I decided... probably made the hardest decision, this was definitely not by chance, made the hardest decision in my work life, which was to leave the family business. I had been there for six years, and had done some really fun things like starting another summer camp, which was really amazing.

But it wasn't, it wasn't good for me. Sort of, I love building things and I really needed to feel free to make the decisions I needed to make to build. And I was weighing way too much, way too young in my career around trying to please other people. Right. Which wasn't anybody's fault, but my own, but that's what happened. 

Erin: And that's a natural thing I think to dip into when you're dealing with family dynamics in terms, like the people pleasing thing is a real thing and they can exist a lot in the nonprofit sector and especially for women in particular. and then you layer on family dynamics and the pride you feel in the business that they've built, but also perhaps the level of disappointment and what kind of connection you feel to doing the actual work makes total sense.

Gaby: Yeah, I think it was. I mean, there's so much about it, but I think it's also like the expectation that this is what you're going to do for the rest of your life. Again, in my mind, that was the expectation. I don't know. I can't speak for the people around me, so you feel responsible for the future.

Erin: Yeah.

Gaby: So anyway, story for another time, but I'll just say the hardest thing I ever did. And was able to do it with. Love and good connection with my family, which was probably the most important of all. And so from there, so that was absolutely a strategic decision. Very, very hard. And I went to business school during that transition because I needed more confidence in my own abilities. The other thing that happens at a family business is you're like, do I deserve this role? Or was I just given this role?

Erin: Mm.

Gaby: And so business school was an amazing opportunity. I went to Babson, you know, entrepreneurship. I just, like I said, I love to build things. It was very inspiring. And then from there, I was ready.

I was ready to go. I had my confidence and I had, you know, some new skills behind me. Did a little bit of for profit work. It was during the dot com insanity. I worked at two different tech companies. And I was really more marketing and sales than anything else. Which was super interesting and super fun and really hard.

And I remember thinking at one point again, so I guess this is a strategic decision. This is really interesting, but I'm not super inspired.

Erin: Mm.

Gaby: interesting issues. Like I got to see Steve jobs talk like there's all these really amazing things. Right. But I'm like, I'm not super inspired to sell peer to peer networking software.

Erin: Yeah. It sounds like some level of purpose was missing.

Gaby: Yeah, I mean, again, I love, I love computer programmers. I mean, they, they taught me a lot about sometimes you just need to be very calm and cool and your decision making. And I can be very all over the place sometimes. They really helped me hone in. At the end of the day, I was like, I just, I'm not feeling it, not feeling it.

So I actually went back to TERC just to talk to the people that I worked with, you know, now we're talking at least 10 years later, because I wanted to understand why I was so happy there. And I was so happy there.

Erin: In the executive assistant role. 

Gaby: In the executive assistant role at a nonprofit. And I think what I discovered is that at a small nonprofit, you are given the opportunity to do just about everything.

Erin: Everything. What a great way to learn what you're good at, too. I had one of those roles right out of college. I didn't realize how generalist it was. I still reference those days because I was like, Oh, yeah, I could have taken that role in so many different directions.

And where I ended up taking it makes so much sense based on where I am now.

Gaby: Yeah, where were you?

Erin: I founded the Tufts Jumpstart Partnership.

Gaby: Oh, yeah, yeah, yeah. Well, I knew you were at Jumpstart. That's, yeah, that's great.

Erin: And what I realized, I mean, in, in, in total truth and disclosure, it was a role that was about supporting, you know, early education development for young children. I was a child development major, which made sense, but what I really love doing and excel at is recruiting students and helping them feel like it. Reaching their hours requirement for AmeriCorps 300, 600, and 900 hours was quite unquote totally doable. I had this whole plan, totally doable. I brought in, you know, so many students such that Tufts took on the program as a fully established part of their Tisch Center.

But I remember like I would come in, and like to evaluate what was happening in the classroom and nothing was going wrong, but I didn't belong in the classroom. I definitely belong in the, you know, in the, in the nonprofit growth and administration space. And I was like, okay, I see that now. So not child development, but organizational development. Got it.

Gaby: It is, it is important to learn along the way the things that maybe aren't your strength, which, which is actually a beautiful thing, if you really can be, that's fine, because then you just look for amazing people that do that thing, right? You're like, okay, so you had to look for people that get into that classroom.

Erin: Yeah, I had to bring on the team leaders who really were good in the classroom, but actually I didn't realize this connection. Not that it was a family business, but my mom was a preschool teacher and director. So there was some aspect of like, she's good at this. I should be good at this, but you know, the development piece that was most interesting to me was not in the classroom anyway. So you went back, you talked to the TERC folks about what was so exciting.

Gaby: And I was like, yeah, I was really happy here. What am I going to do to get back into an organization like this? It was very general. Get me into a non-profit. I mean, I knew nothing about the different kinds of nonprofits and just got me into one. And so I was able to get into another educational research organization.

And I was the head of marketing for a software product that they had, right? Because not just it's a, your tax designation is a non profit. Many non profits, and I think this is a really good thing, have a revenue generation, have pieces of their programs or they have products that they sell. And so this was an organization that focused on using technology to help people with learning differences.

And we had some different software products. So my job was actually very similar to what I had been doing in the tech sector. I was going to trade shows and marketing and talking to different groups to sell and do, and, and doing training definitely did a lot of training going to different schools and different groups on this particular piece of software.

And it was great. It got me back into the nonprofit sector. It was a lot of fun. And so here's something that happened by chance, very happy there, as I had my first child. Before I went out on maternity leave. I had been working with the developers for the next iteration of that piece of software. And it was a huge learning curve for me.

Again, nonprofits over and over again. If you want to learn, if you want to be thrown into something you've never done, and everyone trusts you to move it forward, this is your, this is your place. So all of a sudden I'm becoming a software producer which I really did not know much about. But had a lot of fun, understood the consumer very well, and then was working with some great programmers.

So we were pretty much done with that next version when I went out on maternity leave. When I got back, it turned out that that software was sold for seven times annual sales to a different educational company. Right? Which was an amazing thing for the non profit. And when you know, the head of finance brought me into his office to tell me that I was like, "That is amazing!" Uh-oh.

Erin: Uh oh. Uh Oh. Maybe not amazing for my job security.

Gaby: But it really was, you know, so obviously my job wasn't necessary anymore. I was the head marketer and developer of this product. I was very proud that it sold. I was actually kind of amazed, you know? 

Erin: Can we just pause on that for a second because I think that, that mindset of like, bad for me, great for the team, and I'm so proud, like, not to say that lots of things are bad that have happened in your career are bad for you, but like, I just think it speaks to your team, your, your team first mindset.

Like you, I think you're, you're always about what's best for the greater whole. And I think that's a perfect illustration that I didn't even know about.

Gaby: Yeah, it was definitely a very it wasn't easy, right. but I wasn't, it wasn't like your job is over today. I mean, I, the organization was so supportive of me and just said, you know, we're not letting you go. We really would like to support you to find your next job.

Right. So, that was unbelievable. And obviously, we had some extra cash around. 

Erin: Someone had built something good, so there was cash. 

Gaby: Right. so this was, this was a chance. So I was actually that night going to have dinner with friends of mine and my husband and I was speaking to my friend Paige and I said, you know, I, I just want, you know, I might be feeling a little emotional right now. So... But, you know, I need to find a new job

Erin: mm,

Gaby: And Paige said, okay, well, you know, we got you come on over. So I had dinner. I hadn't really gotten to know her husband very well. But anyway, we had this wonderful dinner and then he said, he said to me afterwards, you know, I'm on the board of this nonprofit and we're looking for a director of operations and I think you should apply.

Erin: mm, 

Gaby: That's just luck. That's not a strategy. That's not anything. That just happened. So I got that job. That was at Discovering Justice. So that, that was wonderful because I'll tell you that was going from a research organization, which is pretty structured, to a real entrepreneurial social enterprise, you know, that was that had a mission, which was to bring civics back into the schools and was really open about how it was going to get it done. And so had some really amazing strategies already in place. I never knew something like that existed, right? Because I have only been in research organizations.

Erin: Mm hmm. 

Gaby: like that it was that job that really helped me hone in on what I love to do and, in fact, introduced me to things I didn't even know I would love to do. I went from being operated on. We definitely had a moment, which is kind of how I met you, Erin, a moment where the organization almost went under and was able to find amazing consultants. Don't forget, there's people outside of your organization that know things that can really help you. And went from being operations really to becoming a fundraiser because we had, we had fundraising issues.

Erin: Mm hmm.

Gaby: I, I remember coming home to my husband when I was told we had three weeks of cash, which I remember thinking, why, why are you telling me? I'm the operations person. I'm not, I'm not the person who brings in the money. But when I went home to my husband, I said, Oh gosh, you know, I love this organization, but it looks like I'm going to need to find a new job again because we only have three weeks of cash. And my husband, who's a sailor, said to me something that I hold dearly, because it really is true. He said, "Calm seas do not make for a great sailor."

Erin: Mm.

Gaby: And I was like, damn, he's like, I was like, you know, come on. I just want to crawl into a hole. He's like, get in there. Like you love that place.

Erin: Aww. So wise, Michael.

Gaby: Oh my goodness. I know. It's good to get Michael into the story. So honestly, I was like, okay, I have nothing to lose.

And that's when I became a fundraiser. You know, and, and it was, like, in a sense, the biggest break of my life, right? Like, so in a sense, by chance, because it's not something I thought I wanted to do. I didn't even think about it. I didn't even understand what it was and how you did it.

But once I started fundraising and all of its shapes and forms, it taught me that if I really cared about something, I really cared about a mission, I could get the resources to help build that mission.

Erin: Mm.

Gaby: And that is incredibly motivating, powerful, and inspiring. And I think the rest of my career, like, I guess I'm focused more on the early, but I really feel like that's what set me up because from there, there were things that were by chance, there were things that were strategic, you know, that I got to really think through, but I always knew, it's a weird thing to say, I had my own back.

You know, I knew that I could, I could play that role. And it doesn't mean you always can bring money in when you need it, not by any stretch of the imagination, but I knew that I could take my own passion and my knowledge about a particular issue and share that with people who had resources and they were interested in getting involved. And that's just an incredibly empowering thing.

Erin: Absolutely. Well, it sounds like that was such a pivotal moment for your future, but also kind of like a full circle moment for everything you've described up to that point. Like you, you learned about executive leadership, you learned about business best practices and you went to Babson, you did marketing for a nonprofit quite successfully leading to the sale of the product. And all of those things combined now kind of like. helped you realize this. Number one, you can do fundraising. I think anybody who has known you in the last, I don't know, 10, 20 years would be shocked to know that you didn't always know you were a fundraiser. So that's just, I think it's so helpful to hear the origin story of that for you. Because for the rest of it's like, yeah, she's not only a fundraiser, she's a powerhouse fundraiser.

And you learned it when your back was against the wall. Three weeks of cash. Wow. I mean, in some ways it was probably good that you didn't totally appreciate what that means and hadn't seen, you know, cash reserves in too many other organizations. But I think that's such an inspiring and helpful story, both in terms of what we can realize about ourselves when our backs are against the wall and how it can be a moment of real expression and clarity around our strengths.

Gaby: Yeah, absolutely. I mean, like I, like I said, I consider that, you know, if I was a Broadway it was my big break. 

Erin: That's right before the intermission. And you are kind of an actress. You do perform. We don't have to get into that.

Gaby: I do love to perform.

Erin: You can do a plug for your band at the end.

Gaby: That's true. Thanks. We'll do that.

Erin: So if you really care about a mission, you can get the resources to support it. And that also kind of speaks to that purpose you were missing earlier on. Like you, you realize when that purpose is paramount for you.

Gaby: Yeah, you're right. I was not as good in technology sales. I'm not as driven. I'm not as driven to do it. It doesn't. Yes, you are correct.

Erin: Why matters? So after Discovering Justice, there was City Year, is that right?

Gaby: There was City Year and I wanted to go to a really big nonprofit. You know, I was like, okay, I get the small scrappy. Love it. Love it. Let me go see how the big organizations do it. 

Erin: Well, that, that was the one at the time, right? The big one.

Gaby: Yeah, it was. And I actually worked, I didn't report to Michael Brown who's the, one of the co-founders, but I basically worked directly with him. I was Director of Major Gifts all of a sudden for City Year National. The thing that's so interesting about it though, and I only stayed there one year is that City Year was very big and everyone had their super specific roles and I found that too narrow for me.

It wasn't like I learned a ton of things at that organization, met some amazing people but I didn't feel challenged.

Erin: Yeah. You need a little room to move.

Gaby: Yeah, 

I felt, I felt more constrained than I felt excited.

And I just, you know, within the year knew and chance fell again. I guess there's a lot of chance, Erin. I may, maybe, I don't know.

Interesting. I don't know what other folks you've interviewed, but I was having lunch with a really close camp friend of mine, Deb Samuels, Deb Donahoe Samuels. She and I had been camp counselors together when we were in our teens. And she was working at a camp as a director. And I knew I needed a co director, like. And there's things about her. She and I were a good team because she is a little bit more empathic. I would say that one of the things I always need around me is someone who's a little more empathic. 

Erin: Mm. 

Gaby: Because she'll get a sense of morale, we need to change some direction, you know, where I, I think I'm getting better at it.

I've learned from people like Deb. I've learned with, you know, from people like Adam Ranke that Erin and I worked with, that for me, it's one of my blind spots. I can walk through a room where everyone's, the morale's terrible and I'll be like, what a great day. That's not really helpful as a leader, actually.

You need to kind of sense what's going on. So we were having lunch, And she was at that time, she was the director, she was the executive director of Crossroads for Kids, a non profit that had a camp and served kids who Didn't have the means and she was doing really amazing things. she just had sort of a tragic thing happen with it wasn't, she didn't fire her head of fundraising and the, and the woman did not quit either, but she had an absolute. I think, I don't, it was something in the family, something, you know, I don't know if it was a loss of a family member, I don't remember, but it was big enough that Deb was saying, you know, I don't know if this is, I don't know if she's going to stay. I don't know if she can stay. And so I need to figure that out.

And Gaby, do you know anyone who is available who might be able to help? And, and she goes, and I, I'd love to work with you, but you're at City Year and you're probably really happy and it's all good. And I just said to her, you know what, Deb, I'd be happy to do that job. I was like, if you need somebody, I said, I'm not that happy.

You know, I'm not feeling challenged enough. And, and so that was my next role: going to crossroads for kids. That was a great opportunity, but logistically not feasible. And so that's an important thing in jobs as well.

The, the camp on my commute it was 90 minutes each way

Erin: Ouch.

Gaby: Really needed to be there and it was good in terms of working for someone I knew well to say, you know what? Let me get this strong and up and running, but I don't think this is going to work for the long haul.

So, I was there for two years and, and that gave me the opportunity to be very strategic in my next move. And that is when I went to uAspire.

Erin: Woo hoo!

Gaby: So that was very much like I knew, first of all, I had met Bob Giannino before. In fact, he had offered me a job when I went to City Year, but. It was very similar to Discovering Justice in my mind at the time. That's a small organization. He had big dreams. I thought he was amazing. And I said, go to the big org. See, see what that's like. Like, don't just like, don't go to something that's familiar. Go to something that's unfamiliar.

Erin: Mm hmm.

Gaby: And when I put my head back up and I was at Crossroads and I reached back to Bob, He had done so much in those three years. It was a different organization. He had brought on Erin Cox.

Erin: Mm hmm.

Gaby: He had the place of just, it was going places and he needed someone to oversee fundraising and marketing.

Erin: It was going all the places, whether we meant or not to whether we meant it or not. 

Gaby: It was going to all the places. And wow. So. I'm going to say that was strategic and I nailed it. That was a great ride. That was a great ride. So I worked with amazing people. We got to build something. We supported each other. You know, there's always ups and downs, right? But I was there for nine years. And that's where I really got to, I guess, try out and observe different strategies, right? Like really different. We really did try. A lot of things, some which didn't work, but some that worked beautifully. And it was, it was really an amazing, amazing ride. And then my

Erin: I would say that was true across also, like, not just impact models, but I think you brought in such creativity to development, marketing, and then also the leadership of our Massachusetts work, like the creativity existed everywhere. Maybe too much at once at times. Probably was my job to reign that in, but I was having a great time.

Gaby: Well, that's the thing, but the, the, and that was an interesting balance between you and Bob, but Bob was like, bring it on, bring it on, bring it on. Right. And so it was learning. That, yeah, we could be really, really creative and, you know, Erin, thank goodness. And we need to focus if we're gonna, if we're gonna get where we really want to go.

 And I got to play a lot of different roles, and hire some great people. And wow. I mean, that, that was, that was a lot of growth. And so. You know, when I had been there for nine years and I, I think the bottom line for me was I was ready to lead something. I just felt that Bob was not ready to leave.

I don't know if I would have been the right leader, but I was like, wow, I would love to do that job. Like that just, I really felt that. And, you know, you can't kind of go to your CEO and say, Hey, look, I'm ready to lead. Are you ready to move on? You know, you don't, that's not really a conversation you have.

Right. And, so I started looking for an organization that I could lead. And I thought a lot about Bob Giannino first coming to what, what was then Access and then became uAspire. Because he found the right organization for him and he saw something much bigger than what it was and he jumped in. And I thought I need to have that kind of lens as I'm looking, I need to find something that I don't need to be running and successful.

In fact, arguably, maybe not my best strong suit. Like once something's really up and running, like really putting in place those key systems and all those kinds of pieces, probably not my strong suit. My strong suit is building. And, so I wasn't afraid again, knowing that I could fundraise, I wasn't afraid about the money.

I was afraid of everything else. What is the board, you know, what is the, you know, the board in particular and making sure, and and was it a good product and was it a solid mission and could I really get behind it? Because even though like. The work I do now, which is focusing on women from underserved communities to, to be able to launch and build businesses, right?

Beautiful mission. Love the women that I meet. But when you first come across a new mission, and I was so steeped in the uAspire mission, focusing on young adults going to college and making sure that they could afford college, right? I was just, it was in my heart, my head, my stomach, everywhere. And so no mission felt like an absolute home run.

And I think, I kind of more rationalized the mission, but what happens, and this happened with Access uAspire, is that as you get under the hood and really start to understand a different area, a different social need, the individuals that are impacted by that. You become a believer. I did know that I needed to take the leap, even if I didn't feel that at the beginning, because honestly, I remember coming to work for Bob and saying, I am excited to work with Bob Giannino. I'm really excited to work with Erin Cox. College affordability... I don't know. Right. 

And then, and then I just became such a passionate advocate for the work that we were doing. So. I knew that would happen in time and, and the center for women in enterprise, it kind of had some amazing, interesting, I'd say bones about it.

Like it had a lot. What it didn't have are some of the things I could bring. And so that was really exciting. It did have a wonderful board. And it still does. I hope we've been working together. I think it absolutely has an incredible board and that's so important. So important. And I could talk about that for an hour and I won't, but it's incredibly boring.

That's what made me want the job really, really wanted. It was when I met the board chair. 

Erin: Oh, wow. 

Gaby: Karen Copenhager. And. I just was like, we could really do interesting work . This leader is amazing. The women, the women I had met during the search process, the other members of the board, I hadn't met everyone, but I was like, these guys are, these guys want to get it done. They really want to do big things. And they have, they have been a part of the organization for a while.

But they, but they weren't stuck in their ways like that at all. Like, you know, I sort of was pushing on those edges and I was like, huh. The organization had grown tremendously in the last probably five to eight years before I got there. And it was kind of a mess in an infrastructure sense. Again, big infrastructure, not my strong suit, small, messy infrastructure problems. Oh my gosh. Super fun. 

Erin: You're all over it.

Gaby: I, yeah, love it. And definitely had some financial and fundraising needs. So I thought, you know what, let's do this thing. 

Erin: Mm Mm 

Gaby: So very much a decision, right. It's more of a strategic decision. And it's, it's, it's been amazing, not, not easy, right? Like this is my first rodeo being you know, the CEO with the fiduciary board and the responsibility of the organization and making payroll and really moving a vision forward. And we could have a whole nother discussion on what is strategic success and what's just darn luck, but there's been a mix of both been a mix of both, and the organization is really, really thriving right now and I'll tell you one thing, the really interesting piece coming from uAspire, to the center for women in enterprise is I just sort of assume that culture just came with the person, right?

So, so uAspire had, and I'm, I hope still has a, just a beautiful culture, a culture of non hierarchical in general, right? Really supportive of people at any level or space within the organization to have a really interesting idea. That is at least worth listening to, if not, maybe to think about seriously, right?

It wasn't all about Bob Giannino decisions, right? And it was for whatever reason, it, it, and maybe because it had grown so fast it was very, the staff were very discombobulated. And so there was just this feeling that the leader was going to make the decisions, you know, sort of across the board.

And I do think it was a little bit about, That moment in time for that organization, but I thought, you know what, I'm going to come in and they're going to see that they have power and we're going to start building this thing together. Well, that takes a while. You know, I'm about 5 years in, I would say 3 years in, we were starting to get there.

And now I just, I really feel it. We just did a strategic plan last year. It was the second one I've done with the organization. It was completely different. It was staff driven, you know, the first one really had to be driven by me because the staff wasn't ready, maybe didn't even trust me enough. And I was like, I gotta put some things in place we have to at least have a plan so we're moving together.

This last one, totally every department has its hands all over it. We did this together. And that has. paid off in amazing ways because the staff is really owning the implementation. It's just, it's incredible, 

Erin: I wonder what you, yeah, it sounds like that's really been a journey of, of trust building and shifting culture. I wonder if there are either key moments or key like mindsets or approaches that you applied to that, that you would kind of say were key to success.

Gaby: Yeah. It was first building the leadership team, the right people on that team and that team needed to trust each other. And that's not an easy thing either, because. that doesn't have a lot of strong, supportive internal capacities, you know, around HR and management and all that kind of stuff, it doesn't feel good.

It's not anyone's fault. It just doesn't feel good. So, I had incredibly talented individuals that were like, what do you mean you want me to. What do you mean we're going to meet once a week? That just sounded insane to people. Now we meet, now we meet twice a week. Because we get so much done and it makes sure that we're, we're in, good lockstep with each other. But, so I would say one of the biggest things, and that was not easy. That was not easy. People did not trust me even asking them to do certain things. You know, I think there was a general feeling that we can't wait for you to lay out the strategy.

And I was like that's not how this is going to work. I am not an expert in helping women launch and grow businesses. I'm a builder of organizations, so we need to come together and use all of our skills together. But I would say one of the biggest breakthroughs is we did use an external consultant, one that we used at uAspire. Danielle I'm going to not say her name correctly. Maybe you can help me. Giannone?

Erin: I think that's right. She is at the Pinnacle Leadership, if folks are interested in looking her up, I should have her on this. Yeah.

Gaby: Oh, you should. Anyway, she worked with me through a couple of retreats with that team. And I would say it was her in combination with Brené Brown.

Erin: Hm.

Gaby: So if you want to understand how to build trust and have really hard and real conversations, dive into that. One of the biggest things from Brene Brown, and that Danielle really helped us understand how to implement well, I'll just use the phrase, which is "clear is kind."

Erin: Oh, I say it all the time.

Gaby: Clear is kind. In fact, it's so, it was such a big thing and I'm holding this stone right here, because I got for, for holiday, I got every member on the leadership team, a, you know, stone, like a beautiful stone that you hold and you can, you know, it just feels great. And it has engraved in it, clear is kind, and what's so nice, and I have done this, is when I have to have a really hard conversation, I have it in my hand. And that has just proven to be true over and over again, and it's probably the thing that hurts organizations more than anything else, is that people are not clear with each other. 

Erin: Beat around the bush. Not clear about priorities. Not clear about expectations.

Gaby: What's Yeah, what's not working. 

Erin: Exactly on that point, I talk to leaders all the time either in the team or the executive coaching I'm doing, and they want to know, like, how long is it going to take? Right, like let's have a retreat or let's have like three sessions bang through it and boom, the trust will be there.

And then I think they're more skeptical. I often see the younger generation who's like, well, someone just said this to me in a team session yesterday. She said, what do we do while we wait for the trust to build? And I was like, Nope, we can't wait. We got to engage in behaviors that help to build trust. This is not something that happens to our earlier conversation by chance. We have to, we have to make the choice to dive in and figure it out. How long would you say it took your team to get there?

Gaby: Gosh, I'm gonna have to ask them. Maybe I'll ask next week. 

 Oh, I guess I would tell you this. We are still working on it. You have to keep working on it, but I would say we got to a real groove... two years.

Erin: How did you know? What was like a key tell for you where you were, where you saw a different possible future?

Gaby: We, Oh, you know, we had started you know, I guess the other key piece, even without trust, you can hold each other accountable in a caring way. Right. And I think that's a big, big thing. And it's funny, Erin, we, we, we talked a lot at uAspire, we're like, we got to hold, we got to hold each other accountable.

And I remember, I remember being in that room going, how do you do that? How do you do that? I don't know how to do that. It's like, how do you hold anyone accountable? I was like, if they don't do it, do you put it like a dunce cap on their head and put them in the corner? Like, how does that work? But now I think I completely understand it, which is just every time you meet, you check in with each other about the things that you said you were going to do. You ask people questions like you said last week you were going to do XYZ. How's that going? That's it. There's no dunce cap. There's no pointing fingers. 

Erin: It's a consistent follow up. 

Gaby: It's consistent check in in a caring way because one thing that's key, I am not a finger pointer. We are all in this together. Like we are Don't, you know, maybe I'll write a book: Don't Lead Alone. Like, don't be alone. Don't feel alone. And believe me, sometimes I do. Then I remember I've got a team, I've got a board, I've got people ready to help me with whatever's bothering me or troubling me right now,

Erin: Mhm.

Gaby: Even if it's something that you know, maybe you can only work with one person because it needs to be, you know, sensitive information, but there is someone in your organization. If there isn't, you better find one and develop that person, but you do not need to solve these things alone. And I feel really strongly about that. So I guess when I knew that things were really working like that, that I just, I felt like not alone at all. I felt like I had my peeps and they had each other. They were having meetings, tons of meetings without me. Solving things left, right, and center. Part of working with Danielle also was how to give feedback to each other. And we did that. We did that. It is not easy. It sucks. And it's the best thing you can possibly do. And we do that over and over again.

And I guess here's another piece. No going around the back, right? If I have feedback for a team member. Well, let's just say as a CEO, right? People will come to you and say, so and so has done such and such and I'm so pissed. Right. And my inclination is, Oh, I'm going to go to that person and I'm going to fix that.

But no, so wrong. Right. You say, gosh, how are you going to bring feedback to that person? What's your plan? And I don't always succeed at that. If I try to jump into the fray and try to help something between two leadership team members or a leadership team member and a staff member, it's absolutely not the right thing to do.

It happens. It's like my, my gut is I want to help, I want to solve. No.

Erin: Yeah, well, it builds this expectation that all roads lead through the leader. I'm working with a couple leaders who have centralized themselves in the way they run their organizations and I think this was in some ways necessary for many organizations that were particularly impacted in the pandemic. Like somebody needed to make the decisions and run the communication and figure things out. For many organizations, especially place based ones, they were in crisis for a couple years. And they're coming out of that now, and they're realizing that what we're referring to as this hub and spoke model, like the leaders at the center, and the pathways just lead from the leader to the individual people who run the functions. But those functions don't have pathways to each other unless they go through the leader.

The leaders are realizing like there's a weight to this, both a heaviness and an inefficiency and we're transitioning that to more of a, in this one organization, it's all women, so we're calling it Ladies of the Round Table. More of a model that's based on a circle where everybody has pathways to each other, but you need to figure out how to build them.

It's a really hard transition because the leader needs to figure out how to decentralize themselves, but still step in on the things that are most important for them to decide or lead on. And that can be hard to figure out. 

Gaby: No, absolutely. It's really interesting hearing you talking about that because the way I see my role now is people will bring stuff into the leadership team. You know, again, I'm a little bit too much of a Brene Brown, but rumble, right? Like, like people's jobs is to really bring in their perspective.

And that was another evolution, right? For my finance person to really believe that her opinion on the program was really valuable. She's been there for over 10 years. She understands the program. Just, you know, she's sometimes at the beginning, she's like, well, I'm just the numbers person. I was like, you know, you're really so much more than that. Like you really understand how the program affects fundraising and the expenses and like, we need you to come in. Right. But what I would say is like, we need to rumble. And if we can't figure it out. all leadership team members being pretty much equal, if we cannot get to a solution, I will make the call right or wrong. I promise that's my role. I will make the call based on the information that's on the table, because 

Erin: That's the fallback plan, not the default.

Gaby: That's the fallback plan. And that is about saying we're going to leave here with clarity any which way. Now, the, the, the issue with that, right, is I might push for clarity too soon.

Erin: Wait, I can't help but think about how we decided on our new name because I think it's a perfect example of what you're talking about. So listeners, picture this. Circa, I have no idea what year it was. I don't know, 2014, 2015, somewhere around there. were meeting as a leadership team, and we were grappling with a name change because then called Access, we were no longer just about access to higher ed. We had a suite of programs that covered grade 7 through 16, if you will. And we needed a name that represented this broader vision and national potential that we were starting to realize that Gaby was head of, of development, marketing communications, and we were a group that at times struggled to make decisions.

I think that's a fair statement. And so Gaby was working with outside groups And, you know, we had done all this work. We're basically at the point where we, we, should have been ready to make a decision. But we weren't. And so picture this. We all learned that day that our big conference room, the Center for College Affordability in our old office space. We learned that day that that room had a lock on it, Gaby, because Gaby locked us in until we made a decision. And I was, I will never forget that. And I think it's a great example of you, like, not only, you know, appreciating the timeline and the need to make a call, feeling the readiness and just providing clarity and a push to get folks to lock in. And we did,

Gaby: We did, in fact, to, to, to give credit where credit is due, we, I think we had the name, I think I locked the door when we didn't have the tagline. Yep. And I have to say Erin Cox pulled it out because I have to say, once I locked the door didn't take long. I don't know if you guys all panicked or what,

Erin: If you take away anything from this podcast today, feel free to lock your colleagues in a room, because it'll really inspire decisions. Yeah, no.

Gaby: You're the one who you just threw out, "Prepare, Afford, Succeed." And we were like, boom, done. 

Erin: People had trains to catch. I was, maybe I was just the first one to speak.

Gaby: Yeah.

Erin: But it happened. Yeah. I think it was just also a sign of not only your, your leadership and you're willing to push a group, but also you did it with, with I don't know. I still, I, I, obviously I crack up when I think of it. I was like, that was bold and we needed bold. We needed to be bold at that moment. 

All right, Gaby I feel like we've pulled apart so many of the different strengths that you bring to the table, but I'm curious to hear you sum up your strengths as a leader. What do you think about them now? Cause you're also like an accumulator of experience and learning. So my guess is they've evolved over time.

Gaby: Yeah. Where I. Where I see my greatest contributions, let's just say I now feel like I really do know what it takes to build strong teams. You know, I've always loved working with teams. I've definitely had some success with teams before being at CWE, the Center for Women in Enterprise. But now like, I'm like, you know what, I really can do this.

And if you have the right people, it's amazing, right? It's just amazing. And it's the most powerful thing to feel your organization is to have that, that really, because also, and then can that team build its teams, right? I would say that's a really hard next step. And I would say at five years, were there too, but I would say two years ago, it's like, how does that happen?

How does your amazing team now build their teams? Right? So there's all these mysteries of life so I'd say that's probably the number one. Number two is I was just thinking about, I think Erin, we did one of those strengthsfinder things 

Erin: yeah. 

Gaby: and, it came out that I was woo, 

Erin: Love the woo! There's no strangers! Only friends I haven't met yet. That's your tagline. 

Gaby: And so I want to say, I want to say strategic woo. I mean, I love people. There's no question about that. Getting better at, at choosing where I need to be and how I need to be and that kind of thing. I love telling people about the organization. I love getting them engaged and involved and I can frame a vision, right?

So woo is, yeah, I got that. I got that. And then I would say that the third thing is that I, not only have the ability, I absolutely am committed to delivering difficult information in a timely manner, you know, with compassion. And that's a hard one. And I struggle with it because there's nothing, there's a lot of things that are information you need to deliver to folks is hard.

For example, letting someone go incredibly hard, right? Or telling someone you know, that the thing that they did, let's talk about what worked and what didn't work, but let's talk about it. Let's talk about it the next time we meet, not in five months at a review, right? Because you have incredible potential. And here's some things that I think you could do so much better. And how can I help you work on those things, right? So it's really remembering at all times why you were given this role as a CEO. You were given this role to move the mission forward. You were not given this role to be the one that's most liked in the room. You weren't given this role just to employ people. 

You were given this role because a group of volunteers, passionate volunteers who have other full time jobs, asked you to move that mission forward. And so that gives me the support and the strength when I hedge on that to really be consistent and in communicating clearly and kindly.

Erin: I love that. Can I, can I connect all those ideas for a second? Because they're coming together for me around this concept of just seeing the potential of people, of organizations, and people inside and outside. Like, it would always impress me when you would you would go to all these different networking meetings or all these different events, and you'd come away not only with like, you know, five business cards or what have you, but you with each person, you made meaningful connections and found a way to connect them to your work and to be helpful to them.

Like, I think that your creativity comes out in, well, one of the ways it comes out is just in like seeing the potential and building the connections to have people advanced, to have organizations advanced, to have a mission advanced. And I, I always just was so impressed by how you put those pieces together. And you also just seem to have so much joy when you're doing it. So Woo makes total sense for you.

Gaby: In fact, joy is one of our organizational values, which is, which is so funny because when you think about COVID, right, we all needed joy. And, I even had a staff member, cause there's so much stress during COVID of course, who came to me and said, I feel like you're forcing me to be joyful. I remember thinking, oh gee, okay, we got it. Oh no. I was like you know, and I think we've gotten much better at defining what we mean by each of the values, but like, yeah, joy. The work we do in probably any job, right? If you're going to do it really well, there are just things that are really hard about it. And, and if it's worth doing, we're going to do those things, which means we need to find the places to have joy together, because we got to sustain, we got to sustain.

 You can't just be thinking about all of the problems that you're trying to solve. You have to like, look at your colleague and go like, that was so much fun. Like that brainstorm with that whiteboard. That was awesome. Let's do that again. Right? So, yeah, joy is important.

Erin: Love that. I know that you have thoughts on some of our other topics, so I want to, I want to jump to another one. How about the best advice you've ever received or given? I feel like you've offered so many different pieces of advice already.

Don't go it alone! Calm seas don't make a great sailor. Or if you really cared about a mission, you can get the resources to support it. But, what else comes to mind? 

Gaby: Yeah, and clear is kind. I think in addition to that. Oh, well, when we were at uAspire, we had different centers for you know, basically moving our program out and I oversaw Massachusetts. I was the Massachusetts Executive Director. So I had a board. It wasn't a fiduciary board, but I did have a board chair, David Hadden who had been with the organization, I think, since its inception. And he is one of those people that knows management. I learned so much from him. But he took me out to lunch when Bob said, you know, when, once it was decided that I was going to be the Executive Director, because I had been really running marketing and communications, but Bob needed someone in that role.

And I was excited about it because I was like, okay, okay. I've never been an Executive Director. And David Hadden said you have to figure out everything that you don't have to do and make sure you have someone wonderful to do it as soon as possible. You have to delegate in a way you never, never even could imagine. And I don't think he said it exactly that way, but it was basically, if you don't delegate, you're dead.

Erin: Yeah.

Gaby: And it's just true. You really have to question the things you're holding onto. And I guess here's another thing, Erin, that Erin Cox taught me, and I can't remember under, it might've been something you had taught the whole organization, which is, is that a have to, or is that a preference?

Erin: Mm

Gaby: Remember? You know, like when you're managing, when you're managing someone, do they have to do it that way? Or is that your preference?

Erin: Mm.

Gaby: And gosh, darn it. I realized how many preferences I had.

Erin: I just did a management training with a group this week, and yeah, I think I've evolved how I phrase it, but it still feels really important. I also flipped it around for them and because we were talking about management philosophy, and I was like, I gave 'em all these questions, to think about in the positive, and then I was like, now think about your pet peeves. What really pisses you off?

Gaby: Oh yes. 

Erin: Cause there's probably some form of an expectation in there. And then we got into, is that expectation a have to or a preference? And you got to be honest.

about that. gosh. Talk about a pet peeve. I don't know if you remember this, Erin, but when I, whenever I ran an event, right, or someone was running the event and I was overseeing them, let's just say, I would come to the event and I always move all the signs, which is just why I did that? So, yeah, you really have to think about your pet peeves because some of them, you know, honestly might be for you.

They might be. And we have to be clear about those, right? Because that's kind. Because otherwise you're going to be pissed. And people won't know why.

Gaby: Absolutely. I have some real things around materials, but I'll tell you, I will tell you, I have let a lot of it go. 

Erin: How did it feel to let it go?

Gaby: Now I've seen materials that kind of blow me away, right? So there's partly that's that. I don't let it go like the woman who oversees our marketing, she's working with a marketing firm externally, and, and they're just, they've just, totally raised the level of quality and all of these things, but we still develop a lot of things in house that don't have her or that marketing company's touch on it.

And if it's something coming directly from me, I am a little bit all over it. And I think I learned that in my very first job going back to TERC. There was a woman there who I adored, who was the head of communications. And she taught me a lot about design in that sense.

And no, I am not a designer. I would be absolutely lying, but boy, do I have some strong feelings about people's attention span, not having attention. Maybe it's because my attention span is small. I don't know. But There's too much coming at us. So if we're going to really get stuff across, we have to be super, well, I guess clear, but also where's the eye, where are they looking? What's, you know, what's going on? So, but yes, letting it go and seeing the amazing, like we have a new website and, and the social media that our organization is producing. It just far exceeds anything I would, you know, but, but it is a pet peeve, right? So

Erin: That's it. Well, and you're also giving us all hope that you can grow out of your pet peeves. So thank you for that. 

Gaby: You can, yes, you can.

Erin: Gaby, I I know you've been so invested in your own learning, so I'm just curious, are there any tools, articles, resources, trainings, you've mentioned a couple of people, but other things that you've used to support your professional development that you want to suggest to listeners?

Gaby: You know, when I was at Discovering Justice and I became a fundraiser I guess, I did go to one of those, and there's a lot of scholarships out there, it was the Harvard Business School's SPINM program, which I think was, I can't remember what all that stuff stands for, but it was for social entrepreneurs.

Erin: The executive education program. 

Gaby: Full week, very expensive, but still, like, scholarships available, and I went to two programs there and they really, they were intense. And they really moved me forward in significant ways 

Erin: Mm. 

Gaby: And gave me an external network that I didn't have. 

Erin: Okay. 

Gaby: So I think, I think there's different programs like that. It doesn't have to be at Harvard. I'm sure they're all over the country with different business schools. so I think that's one. Read Brene Brown, if you can. I have this book, Dare to Lead. She has a lot of books, but they're very dense. Like we did that as a team. So there was a lot we could talk about.

Oh, I know. And you know, this one, Erin five dysfunctions of a team

Erin: Oh yeah, that's a good one. Speaking of accountability, 

Gaby: That is great, so that's a parable for anyone that doesn't know that book. And I can't remember.

Erin: Patrick Lencioni. 

Gaby: Yeah, It's short. Your whole team can read it in a pretty short period of time.

And there's so much in there to work on as a team. There's so much in there. I remember the first time I read it, I thought this was just silly. And now I feel like it's one of the most brilliant team development books I've 

Erin: yeah. 

Gaby: had the pleasure to work through.

Erin: I think one of the gifts that book offers up is that it just, it normalizes that the kinds of things that you're struggling with as a, as a leader and as a team is, is just common. Sometimes you don't want to know that you're just like everybody else, but it can be helpful when you feel like you're beating your head against the wall.

So yeah, those five dysfunctions are powerful examples and ways to work through it, which really, and I think you've offered so much in your, in your talk here around a key part of, of that whole framework, which is building trust. And doing that through intentional, consistent, repeated effort.

Gaby: Yes. Well said,

Erin: Gaby, how can people find you, connect with you, learn more about you? What's the best way?

Gaby: What is the best way? Well, I'm certainly on LinkedIn, so reach out. Make sure you, you, you mention the podcast, which would be cool. Then I can tell Erin I love, you know, if, you are, particularly if you're someone who either is a new leader and you're looking for connection you know, please reach out you know, my, my calendar sometimes is nuts, but it's really fun to see if I can help in any way. But also I learn. There's so much to learn from other people, right? So you could connect with me on LinkedIn. And you know, get on the CWU website and take a look if you're building. And you know, we work for profits, right? It's very interesting that we're a non-profit that helps for profits to build. But definitely I'm, I'm there and you can find me there and you can email me and let's connect.

Erin: Excellent. That's a truly generous offer from an incredibly skilled and passionate leader. So take her up on it. Gaby, this is so fun. I could do this for days but really appreciate your willingness to come in and share your journey with all of us.

Gaby: Oh, well, thanks for inviting me. This was a lot of fun.