In this episode, Derryck Fletcher, Chief Operating Officer of the Y in Central Maryland, explains how he oversees a portfolio that works like several organizations in one, from early childhood and Head Start to before and after school programs, Y family centers, community health, and talent development. He shares how a random job search led to a long career at the Y, and how managing a bank call center taught him skills he now puts to work for the community.
Listeners will learn why leading people first is a core leadership skill, why the Y hires people with deep expertise, and how data and continuous quality improvement guide major decisions. Derryck explains why AI belongs in back office work rather than member facing roles, and he corrects common myths about the Y, from swim and gym assumptions to nonprofit money. This conversation is a valuable resource for leaders scaling mission driven organizations.
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[0:16] We are back with the Heart and Hustle Podcast. Mr. Derek is in the house from the Y. There's so many of them though, Derek. Where exactly are you located in the United States?
[0:25] There's so many whys. We're the why in central Maryland. And so we're anchored in Baltimore, â the heart of Central Maryland. I'm really excited to be with you today, Ephraim.
[0:35] Same man. Wha what was your title at the Y in Maryland?
[0:36] I'm the operating officer.
[0:37] C O O and and and how long have you been doing that?
[0:43] I've been in this role for four years. â it's my thirteenth year with the Y, and it's incredible to believe that I've been here this long. Never imagined.
[0:52] Yeah. I mean, that's a very, very long time. Is it because you were a a â a member of the why and that's what kind of brought you to this line of work? Like what get you to the why for thirteen years?
[1:03] It's so interesting. So I came to the Y because I was looking for a job, â really, truly. And â I felt led with really no history with the Y. Like I kind of knew of the Y and â I knew the song by the village people. And â I just felt led this one evening to go to the Why's website and look for
[1:27] Ha ha ha.
[1:28] Job postings, job opportunities. And we were looking for a leader here to come in and lead our before and after school division. And so I applied. And after a really long search process, the rest is history. When I came here, I thought that I would be here for five years max. And 13 years later, here we are.
[1:49] Was there like anything that you went to college for that kind of led you to here, or was this you just grinding it out?
[1:55] Just grinding it out. I mean, my my background is in youth development.
[2:01] Wow.
[2:01] And so â obviously nobody serves more kids other than the public school district than than the why. And so I was familiar with the work of the Y and thought that there would be some significant growth opportunities there. That's what attracted me to the Y. But still, you know, being a young, progressive, ambitious millennial, â I really thought be five years max. What I did not expect was the opportunity to find home. I found a
[2:29] Yep, yep. Yeah.
[2:30] Where â I could grow and thrive, but also make some incredible change in our community. So here we are.
[2:38] Shout out to you. You mentioned millennial. I mean, shout out to us millennials. â you know, I actually just spoke to putting on an event and I spoke to the mayor of a certain â area. And when I spoke to her, realizing we actually walked the halls together, same school. She graduated in 07. I graduated in 08, and she's the mayor. And I'm like, let's go. Like, let's go to the millennials right now. We are definitely taking a seat at the table. Was it difficult when you took the seat at the table?
[3:04] Right. We changed it one. It was incredibly difficult. â I will tell you though, what is more difficult now. What's more difficult now is no longer being the youngest person in the room. â what's difficult now is having unc status. My kids joke me all the time and remind me that I'm a millennial, but I'm an elder millennial, as they say. â and so like seeing this new group of emerging leaders that are coming into the room and pulling up their seats at the table. And I'm quickly realizing that I'm no longer the the you know young whoopersnapper in the room has been really disconcerting for me. I've been talking about it in therapy.
[3:42] Mm. I love it. No, I mean, listen, the unk status, I definitely I get a little I feel some type of way when I hear that. Like, yo, don't do that to me, bro. I'm I feel young. Okay. I still look good. You know what I mean? Stop don't do that to me. But â yeah. But no, man, I I â I appreciate I appreciate you the hard work you put in to kind of get into this role, right? To continue to fertilize the future. What what what does a CEO seat look like? What is your day to day job â with the why?
[4:14] I'd be like talking to you. Well, it's â a little bit of craziness every day comes with its, you know, own surprises. The great thing about the why is that I have this opportunity to use â my business acumen and my strategic brain and my desire to, you know, to to win, right? Like and and and really be effective while being able to do that at an organization that has a charitable mission. â but
[4:39] Oui.
[4:40] That but the opportunity to do that at scale. And so my job as the chief operating officer is to support all of our many operating verticals. The WIS work is so significantly vast. â it really feels like we are about seven or eight different organizations rolled into one. â and so each leader of our lines of business report into me â and they're on my team. And so that includes our early childhood division, which includes like our preschool work and Head Start and Early Head Start and â pre K to our school age youth development programming, including our before and after school work, our community school work, our teen engagement work, as well as the the work that we do in our Y family centers. â So it's like what you would traditionally think of when you think of the Y, where you go with your your key
[5:34] Mm-hmm.
[5:34] Tag to kind of check in, â as well as all of our dynamic community health work. There's a considerable amount of work that we're doing to really address chronic disease, â as well as â to support folks in our community related to the social determinants of health. â With a big bucket of work around social emotional learning, and then some of our strategic talent work also sits in my division. So that includes talent position, workforce development, our learning. and leadership development. And so I'm I'm really blessed to be surrounded by great colleagues who are â competent, smart, and incredible at what they do, but also really good humans that I get to do life with every day.
[6:20] Love that. Good humans is important because that that's yeah, it makes a difference. It definitely does, man. â
[6:24] But It does make a difference. You know, it makes making talent decisions really easy at my seat. So when work for such a large organization, by the time folks get to me in a search process, they've already been vetted. They are are we already know that they are competent, that they're good at the job, that they can do the task. And really what I'm looking for is is there values alignment? Is there mission alignment? Is this somebody I want to be in the foxhole with? Right. And so â it's it it it's the best. This is by far the most challenging job I've ever had, but also the most rewarding one.
[7:04] Yeah, for sure. Were you in the corporate world before this, the for profit?
[7:06] For a little bit of time I w I was a banker. â the financial institution that I used to work for it doesn't even exist anymore. It was bought out by
[7:14] Okay, okay.
[7:15] a really large bank whose name has to do with the name of our country. â but bef before when I worked there I was â actually a manager in the call center and so I y you know, led a team of folks who sold credit cards to people. â and so what I do now is very different. Very different but I've
[7:37] Okay. Yes, it is. I used to be the Derek, I used to be the guy taking phone â phone calls, but for the airline industry. So believe me, I get it. I get the call center vibe, the the phone calls. I I tell you what though, I sometimes actually miss being on the calls. I mean, yours is probably completely different, but mine's just helping people. Sometimes there was this time where you could really help somebody make a difference. Those are the times that I really enjoyed. I I didn't enjoy the calls that people just were entitled and disrespectful. You know, I enjoyed them calls. I was definitely â You got one more chance, or I'm disconnecting this call, right?
[8:09] But you know, but I can only imagine 'cause nobody calls the airline call center absent of an emergency, right? Everything is so self service. If I'm calling the call center, it's because I'm stuck somewhere or I can't get it to do a thing. So I imagine you have to deal with tons of people in crisis.
[8:25] Correct. Yeah, yeah. What what do you think that cost center, just leading that cost center actually taught you that you still use today? I can imagine every part of your journey, there's something to learn there.
[8:34] Absolutely. So it taught me â the importance of being able to use my powers for good. So in the call center I discovered â what I'm good at. I discovered that I
[8:45] Got
[8:46] â can lead and inspire people. I discovered that I could probably sell ice to a Eskimo. â and I just discovered that I like winning. â and I don't like doing things if if we're not gonna be number one. And so working in a very competitive environment, I realized was where I could thrive. Now at the end of the day, not necessarily using my powers for good, right? Like â my my job was to teach the folks on
[9:17] Okay. Yeah.
[9:17] on our team how to sell folks credit cards that they didn't need. And once they got the credit cards, how to convince them to â either transfer their balances from other credit cards to us or how to get them to take like cash advances that they probably didn't need. â and and that as I look back on it felt like incredibly predatory, â which is why I couldn't lend my life right to that. â
[9:43] Correct.
[9:44] And so what I have discovered through a number of different turns, right, like here at the Y, is where I can take all of those hard skills and use that to support building our community.
[9:57] I love that. And and one of the things you mentioned is just like getting the leadership. â you know, I once I realized that I was a leader, I'm like, â wow, I am. Right. And it really starts to change just the way that we think, the way that we start to operate, the way that we realize people are actually looking at us. Natural leaders, a lot a lot of the times, like these, we just have these qualities about us. But in you being a leader and and finding that. what leader did you find yourself being? There's so many different ones out there, man. You know, there's the ones that are on the front line, putting in the work, but i and, you know, s always remembering what it where they come from. But you also seen Derek probably some other leaders, you know, that are are the complete opposite. What are your values as a leader now?
[10:39] So You know, I've had the benefit of working for incredible leaders and I've learned something from every leader for whom I've worked. â and I take different pieces of them with me. â what I think is central for me is leading people first.
[10:59] Mm-hmm.
[10:59] â it it's about the people. And what I've I've learned two things as it relates to leading people. Number one is as a leader, my subject matter expertise should be in leading and inspiring people. â then I go on my team and look for folks who have the specific subject matter expertise to do the thing, realizing that I don't need their subject matter expertise because they know how to do the thing. My job is supposed to be to lead, inspire, and to support them. â and so really leaning into that as an expertise and building that muscle and remembering to put the people first. â and then recognizing that the outputs will come and then eventually the outcomes will come. But you know, recognizing that when folks are supported, when they are happy, when they're in an environment where they feel like they are seen and they know that they have an opportunity to thrive is actually when they're most effective.
[11:58] Yep. Yep. I like it, man. I love I I love it. I love that â you have really good values. You've made it as far as you have in the C suite space. â clearly not the end all be all because you still got so much so many more years ahead of you, bro. Like you're definitely CEO, maybe within the next five at least. You know what I'm saying? If you choose. If you choose. I can imagine it's there for you, Derek. I could imagine don't know. Just speaking to existence. You never know.
[12:19] No, I mean like I am thank you for saying that. â I'm blessed to work for an amazing CEO right now who just celebrated his twentieth year and I keep begging him to give us twenty more. â he has literally changed our our organization. He shifted the trajectory of our organization. our why, our association was actually on the verge of insolvency when our boy bought him in â 20 years ago. And to see where we are now is clearly it's not the same organization. I have learned so much from him and am learning so much from him. â and what I appreciate most is that he's a tireless leader. â and so we're constantly pivoting and we're constantly growing. â what I also recognize.
[13:08] â wow.
[13:09] recognize in leadership is that â there is an art. to to to being number two. â and I've appreciated that in in this role is that â he is an incredible number one and he gives me space to be number two and to own our operations and to really lead our operations while he's out front â leading the strategy and pressing hand to flesh and and and and doing all the things.
[13:54] Yeah. Love it. â yeah, so that means you're in the right seat to take number one at some point. Got it. Got it. Thank you, Derek. Nah, I just joking. â what makes him what makes him so good, Derek? Like what you you mentioned him just being able to make those changes, you really being a part of it because you spent a lot of years under â you know, that umbrella. What was making him so good? What what was the changes that he was doing?
[13:59] â John has a great eye for talent. â and so John believes in hiring people who have really deep expertise in in a particular area and then moving out of the way and letting them lead. â one of the key things that he shifted was around
[14:25] You have a iPhone. â Too bad for you, bro. It's all about Androids, but we'll we'll let it slide, Derek. Just 'cause we're talking about your your CEO. We'll let it slide.
[14:27] I do I do have an iPhone. I do I do have it. And some somebody somehow penetrated the D and D, so I don't even understand how they have it. And it's and it's not a
[14:40] â Hey, they call twice. It's usually â you gotta call two, three times to penetrate, right? Yeah, yeah.
[18:00] It is like this number was not a number that's on my D and D penetratable. â so I apologize about that. But our our our CEO shifted our culture to be one where we as I understand it, we used to hire folks who were jacks of all trade. â and we really looked for everyone to be a generalist. And what happened was we had a lot of folks that knew a little bit about a lot of things. â and he readjusted our organizational structure â and really set up lines of business where we had â a head of each line of business who had deep expertise in that one thing instead of folks being responsible for all of the things within a region. And that just allowed us to scale very quickly. And so what he has taught me is that â I hire really smart people
[19:29] Got it.
[19:30] That I respect. â I actually have this rule. I don't hire folks â who are in a role that report directly to me unless I truly believe that they are smarter than me. Like I have to believe that they are smart. Now there's something that that I'm supposed to give them, right? Like it's still my job to inspire them and to coach them. And we all work on individualized development plans and I'm here to see everybody thrive and want to see them go to the next level.
[22:01] â okay.
[22:04] But I have to fundamentally believe that they are smarter than me if they're gonna sit on my team. That's been the secret to success for me.
[27:53] Yeah, that was good. I I love it. â you you are right. You gotta get someone in the room smarter than you because if not, then how the hell are you growing, right? Like you're you're really at this ceiling right here. If I get more people that n understand a little bit more, of course you're a leader. We talked about it, right? You just lead others to â success pr pretty much. â how important is data in your role, man? We haven't talked about data.
[28:36] Exactly. Exactly. It's it's so incredibly important. I mean, we have a organization where we â employ up to 3,000 folks at a time, depending on the the time of year. We are serving literally hundreds of thousands of central Marylanders at one time. â Our annual operating budget is around $115 million. And so right like our decisions are incredibly consequential. Every decision that rises to me â are pretty significant decisions. And so we're not out here taking shots in the dark.
[29:21] Wow.
[29:21] We didn't get to where we are. by accident or organically. â it's with an incredible amount of intentionality. â and so our decisions are data informed and when I say decisions, I mean both right like the the development of our strategy, but also around how we revise the strategy. So, you know, I I believe in continuous quality improvement. And so the data tells us where we need to refine things, where we've gotten it wrong, when, you know, the the predictive indicators are not suggested.
[29:41] Mm-hmm.
[29:41] that we're on the right path and knowing when when the course correct and adjusts.
[29:44] Is it easier now, you say, with AI? You've been in the role for some time here. You've experienced I can imagine without AI, with AI, is it giving you is it buying you back time, I would ask?
[29:52] It is. It it and and but it's weird, right? Like so because we are in the people business, â the the the research tells us consistently across the board that folks who consume the services of the why, whether they are in a program or accessing the why. through means that they pay for or whether it's means that are complementary to them that a grant or charitable contributions are covering. People remain with the Y because of the people that they encounter, not because of the actual transactional service or because of the machines in the building. It's the people in the building. And we see that across every single point of access at the Y. And so because of that, we can't really replace our member facing associate roles.
[30:22] Mm-hmm.
[30:22] with AI. Like we we can't have automated, you know, folks at the front desk. We we don't we we don't have â AI â agents supporting our our call center. We don't use AI as lifeguards, although some folks are testing it out, right? Like like we're not we're we're not doing that. We recognize that we need the people. Where we are leaning in and where we are using AI is to support some of our back office functions, some of that
[30:40] Mm-hmm.
[30:40] analysis to really be able to look at a myriad of data points to â you know that we have the folks and with the communities we're serving
[30:41] I love how you pictured that, of course. It's to buy back time to continue to do the more of the things that we love, which is that people interaction, which is meeting people where they're at. So â definitely the right way I would say to use it. And I think every why, if I'm not mistaken, they're they're very different as in the things that they may â serve, right, in the communities. What makes you guys so different?
[30:43] Yeah. Yeah, so well you know, the saying is when you've seen one why, you've seen one why. â the beauty of the why as a federated system and a federated model.
[30:44] Mm.
[30:44] Is that each local Y has the opportunity to be responsive to the needs of that community because we know communities vary so significantly. And so sizes of Ys vary. You have some Ys that are very small and independent, and like literally that one Y is its own independent organization versus Ys that are a part of a larger association. And so we are in in Central Maryland. We're one of the larger associations. Our service area includes Baltimore City and then the five counties that surround Baltimore City in Central Maryland. â so you know, we have an opportunity to have some significant scale. I think what makes our Y different in addition to our our our size and and is also our scope and and the breadth of work that we do. So we have you know our our Y family centers, which are a hub. of community â where folks can come and get healthy but also more importantly be able to connect with friends and and and neighbors and and find a a true sense of community. But we're also doing a considerable amount of work in the early childhood space â and in the school age youth development space. It's it's you know and and all wise serve kids and serve families, but we do a considerable amount of our work in schools. So we do it outside of our of our Y buildings. And so we do it in schools and that work starts when the kids are in utero through early head start and we support them post high school graduation in a number of ways.
[30:51] Yeah, I think in my location, we have a small Y. I go in there and and I'm I could run around it in like five minutes. Like it just for them, I could tell they they focus on school. I could tell just by walking into it. Not school. They focus on swimming. So they got it. I can tell that by the pool they have outside inside. And then I guess they must focus like on the elderly, just because the community I I'm based in was a older community. I think it's probably time for that Y to change it up just because, you know, times have changed. But
[30:53] Mm-hmm.
[30:53] I I I could definitely you telling me just kind of the scope that you guys are doing and how big I'm like, â yeah, that's the one next to me is definitely not producing these numbers. But, you know, with a Derek, you never know, you know. No.
[31:04] Tell them to get us we're we're happy to they can come up and benchmark us. We can help our friends.
[31:09] I love it, Derek. No, this is this is really cool, man. â what do people get wrong about the Y? I can imagine that you hear so many things that people get wrong about the Y World. What are those things you hear that we we should just kinda like myth busters here?
[31:09] And so â number one is people believe that the why is just swim and gym. â I think that so much of what they see about the why is promoting membership at the Y that folks think that that's all that the Y is. â and I also think that folks believe that joining the why is joining a gym when when you're not. You're really joining a community, â a community that is invested in the broader community, a community that is a pillar, â an anchor of the â of the broader community and of the region. â the second thing is when people â see the why, particularly it in in communities where there's a large why association, â they believe that. That the Y either has money or is â or has an operating deficit. When the truth is neither of those are actually true on its face. â While we do have a charitable tax designation, so the IRS would consider us a nonprofit. The reality is without margin, there's no mission. â So we have to, you know, generate some sort of profit in order to remain in the black and keep our doors open. Open. â so you know, as any business entity, â we do have to make business decisions to ensure that our organization is sustainable. â we can't, you know, just be frivolous in in our decision making under the auspices of being a nonprofit. â on the counter to that, we also not rolling in the dough, right? Like, yep, we do have a very large budget, almost $115 million a year is what you know what we expect in terms of annual operating.
[31:10] Yeah.
[31:10] revenue. â but the the margins are actually pretty thin because all of it is reinvested into the work of our mission. All of it is invested into creating â community for every person to be able to find a sense of belonging
[31:10] Mm-hmm.
[31:10] and be able to thrive, to give every kid â equitable access to opportunity. That's what we're doing here at the Y.
[31:10] Yep. Yeah. And and all of this, as you mentioned, it comes really from partners in the community. We talked about the internal partnership, right? Of you guys at the C suite level, but that external partnership of keeping those relationships alive and and allowing them to see the impact that is being created within their own communities. I mean, kudos again to the leadership of being able to maintain relationships, build relationships to get to a hundred and fifteen million dollar budget. Am I lying here? Like it's all about relationships building as well, right?
[31:11] It is all about relationships. I mean that that is actually our work, right? Like our our work is community work. It is about â human-to-human contact. â and that is actually what differentiates us in all of our lines of business from other folks that do the things, right? Like there are sure, there are other places where you could go learn to swim. There are other places where you could go work out. There are other places where your kids could go when you need child care. There are other places where your child may be able to go for camp. There are other places where you can go for tutoring or the other places you can go for workforce development, right? Like there's always some other place where you can go but the beauty of the why two things one is there are no other organizations that are doing all the things â and being able to impact and support a community in a very like layered way that's responsive to the individual individualized needs of that community but then also secondly like we recognize that it's not about the transaction that we're having the folks that we're engaging it's really about the relationship Yeah.
[31:12] I love that man. And â I w cause you mentioned a little earlier about you just being able to sell ice to Eskimo. I â really want you to think about some of the programs that you guys offer, â or even some of the I guess group classes. We talked about the relationships, right? They're being built in some of these classes. What are some of those â classes you got to really sell me here now on some of these classes, you know, that people can attend at your Y?
[31:12] Well, the first thing that I would do is find out what you enjoy. and find out what you need. â and I can guarantee you that there is something that will bubble up that we're offering â that both meets the need â as well as entices something â that that you enjoy doing. And so â it it it really depends, right? So it's like, hey, are you looking to get healthy? Do you need to get healthy? Is there â a chronic disease, right, like that you are navigating or one â where the doctors told you, you know, that you're at risk. help you navigate that. â are you struggling with social navigation? We can introduce you to some friends, right? Like we got nutrition classes. We got stuff â that you know will keep you happy. It's opportunities for you to volunteer. Do you want to mentor some kids? Because we got some kids that could use a caring adult that they're not related to. So like, you know, come on. Like whatever it is you need, we we got you right here at the Y.
[31:13] â it. Okay. Yeah. I love it. Meeting people where they're at, it looks like what you guys are doing.
[31:13] That's right, absolutely.
[31:13] Yeah. â Derek, man, as we wrap up, man, what what where can people really be of â of assistance? You know, how can people also invest back into the Y the same way you guys are investing back into your own communities?
[31:13] Yeah, three ways. Number one, join your local Y. â join the community. â And you know, we when you do that, you are investing into your broader community, but you're also gaining access â to I think a a a real gym â and something that will benefit you and your family. Secondly, donate to your local Y. â hopefully you join us, but even if you don't join us, or even if you do join us, right, like making â a additional tax deductible contributions to the Y really becomes a force multiplier. and what we're able to do â and how we're able to support our community and thirdly volunteer at the why â you know the the work is â really deep and it's really meaningful â but there are real opportunities for folks to to lend hands to help and support whether that's helping us at you know more episodically through like a community cleanup or another one-time event or whether it's being a consistent volunteer One of our freshmarts where we are offering nutritious food free of charge to members of our community, completely powered by volunteers. â or whether it's volunteering in one of our mentoring programs here in Central Maryland, we are also the local Big Brothers, Big Sisters â affiliate organization, and so we're supporting hundreds of young people here and providing them with a one-to-one mentor. â and so we we need more volunteer mentors in order to be able to serve more kids effectively. So come join us. Come donate, come volunteer.
[31:14] I love it, Derek. It's been a pleasure talking to you, man. Thank you so much for the insight on what you guys are doing at this level. â all spoken to some different wives, and you guys are definitely knocking out at the park. And I I can't wait to see where else you go, man. We talked about we planted a seed, CEO. So you know, maybe, maybe in the next couple of years. Guys, if you go ahead.
[31:15] No, I'm laughing at you. You're a comedian.
[31:15] â got it, got it. I was gonna wrap up, man. You have anything else to say that you want people to â leave with? Words of inspiration, words of wisdom.
[31:15] No, I I mean I appreciate the opportunity. I think the the the wisdom â now that I told you I have unk status, â that I find myself often given our young and emerging leaders is recognizing that the jobs that we sit in, â they are leased, they are rented. â we have the deeds though to our names. And so there's an opportunity for every leader to really decide who they want to be and how they wanna be remembered. â and that's our legacy. â more importantly, remembering that â who we are at work is never as important as who we are at home. â I had a boss. remind me one day as she was telling me to go home that on my tombstone great boss â would not be what was inscribed. It would be husband, it would be father, it would be son. The people at home are the most important folks.
[31:15] We'll leave it right there. This is Derek. I'm E Frain. Make sure you guys like, subscribe, and comment. And we'll definitely catch you on the next one. I appreciate it, Derek.
[31:15] Thank you, sir.
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