Nonprofit Leadership Secrets: Anat Leonard-Wookey on Scaling with Heart

[0:16]  Welcome back to another episode here on the Heart and Hustle podcast. Today's guest, she was just a kid organizing spices for refugee family and now she's running programs that shelter 7,000 people a year. Anat, that is amazing. You helped welcome a refugee family when you were just a kid. What do you remember about that moment that still lives in your bones today? I can only imagine that it's an easy story to go back to.

[0:40]  Absolutely. I didn't realize it at the time. Um but I uh just how impactful that experience was. But with my parents um as part of their temple um in the in the early8s um we sponsored a family fleeing religious persecution from Russia and we didn't have any connection to these folks other than um a shared community um and a shared hope. Um, and as a kid, I remember um my mom um kind of looking through our weekly grocery list and figuring out how to squeeze in some spices um for this family. And then um I was helping to set up the apartment before they arrived. And I was organizing the spices on the spice rack and I was helping to make the bed um of a kid that was about my age who was coming to a brand new place. and um just having gone through so much and it really showed me the power of what people who come together can do for each other. Um it doesn't have to be because we know somebody or they did something for us, but just that um community that that faith and hope and knowing the impact of safety um it really just hit me at like

[2:11]  So, so giving back has kind of been really passed on right from your mom and what she was doing and now you get to do the same thing. can imagine kids and family you're teaching them to do the same things just a better world for people like yourself this you know a leader and before the master's degrees and before the executive title when did you first feel that like this is this is my work do you remember

[2:34]  yeah so um after I graduated undergrad I my first like real full-time job was um with a nonprofit that helps survivors of domestic violence and their children. And I worked in a transitional housing program. So, you know, safe location, that war panic button on my neck um and really helped um the moms and the kids like regrown, take a breath, feel safe um and work on their next steps. And then at that organization um I became part of uh setting up a visitation center. Um and it was through that work that I met social workers for the first time. I was like that's what I want to be when I grow up. Like that's what it's called. Um and I applied for my masters in social work. Um lucky enough to get into Colombia and that brought me to to New York. But that was that was really real like where it cemented like oh it's a thing.

[3:45]  This is it. Yeah. I I love that it wasn't about the paycheck, right? It was truly about oh I found purpose. I found purpose. Right. Like I found what I could really do that doesn't even feel like work to this day. Does it ever feel like work? Everything that you're doing.

[3:59]  Uh some days are harder than others but I wouldn't be doing anything else.

[4:06]  Yeah. I actually for the you know running a board myself so for the last two days we've been dealing with a situation that's been a year and a half problem and um we finally got it resolved yesterday right we've we took myself and the vice president said you know what we're just going to figure it out we still had a member today says hey so where do I do I need to do this today I'm like it's taken care of like let's go ahead and please let go that problem cuz it was stressful you go into meetings and it's like the same conversation's over like could we just please just get away from this so it is some days are definitely better than than than you know others. Um but it is cool. It's cool that you be you're in a space where we truly give back. Um because that's to me it's what fills my cup. Do you feel that it fills do the same for you as well? Like it fills your cup.

[4:48]  Absolutely. Yeah. Absolutely. Um, and in those moments of hard, um, the thing that always kind of lifts me back up is being able to spend time with my staff and, um, at the sites where the work is happening. And just to kind of see that, um, let go of some of the drama and the politics and, um, all that stuff and, uh, and reconnect with the why. What what are some of your values as a leader?

[5:23]  Um so the first is authenticity. Um it took me a really long time to understand that I didn't have to be perfect. Um that that was uh somehow my expectation of myself and no one else's. Um, and so it took uh it took some time for me to take down my walls and show my real um and uh and the great in that and the messy and the mistakes and and all of that. But being true to me um and showing that vulnerability with folks um really allows them to feel safe to show their true. Um and this is with staff, this is with clients, it's really kind of with anyone. And it is so powerful to be able to um offer safety through that authenticity to build trust um and then do great things.

[6:31]  Um okay.

[6:32]  Oh yeah, another one. You got another one

[6:34]  always. Go with the other value. What's the other value?

[6:38]  Yeah. So integrity um is another huge one for me. Um, and that shows up in a lot of ways and I think it can mean different things to different people. Uh, but for me it means um saying what I'm going to do and doing what I'm going to say. Um, to be really dependable. Um, and to own my stuff. Um, when I make a mistake, it's really important that I name it, that I repair it, and that I learn from it. Um and uh and if I'm able to do that kind of in my position in title um I believe that it creates a sense of safety for others to do that as well. Um and really looking at mistakes as growth opportunities um and uh just keep it moving also not getting stuck there. I love the first one you said is authentic because truly I think as a leader you just have to be yourself, right? Like people work with people and they can see through the BS when you're not when you're not yourself or when you're just I see a lot of people also micromanage as a leader and I was like why do you do that? You know like you do not you have great people you just have to lead them to do the thing. You're not the smartest in the room but all some people just need leadership. Some people just need a foundation, a structure. And if we could be that for someone else, believe me, everything else kind of flows and and just being our true selves. But even being our true selves also helps on the front line, right? Like never people never to be afraid to ask us questions to just come up to us. And I think that's also what happens when you're so real and you're just yourself. Um, so I love that. That was your first one because anytime I have a conversation, I'm like, I don't need the corporate side of you. I want the real side of you, right? Like I don't know. No, that's like you get into corporate, you almost become somebody that you're not in a sense. I'm pretty sure you've seen that plenty of times, right? Lived it probably. Um because we are we we have to that's what we're I think you know when I think about school I think school teaches us that you know they like you're going to have this nineto-5 you gota to do certain ways and in reality you go out in the world and realize like it's actually not like that you know or or it's something that we created and I'm happy that you now have a team of people that think like you because now we're actually building up leaders that are not having to um put on a mask or you know play this role. I'm a COO. You are not the person that always loved doing what you're doing. you just now have a title. So, I like that. And now you're leading the, you know, you're running one of the largest interim housing programs in Silicon Valley. How does this happen?

[9:08]  Yeah, it's been an amazing journey. Um, and a bit of a roller coaster, right? Um, as is I think life. But uh I you know from from my masters I was in New York um uh for for 12 years and I figured if I can like really uh succeed in social work in New York then I can probably do it anywhere. Um I only had you know Sinatra in the back of my mind on that one. And uh um and it was it was wonderful. I learned so much. Um, I uh became a clinical coordinator for a men's shelter on the Bowery and kind of to your point that people can see through you and won't take any BS. Um, those folks and those experiences taught me so much and I am so deeply grateful for that. Um, and uh, and just kind of kept growing. I loved working with clients, but I also really loved supporting staff. And there was a lot of crossover in how I could um kind of use my skills to to do that um in in all the ways. And so uh then I was ready for a change and and I came to San Francisco um and uh and it was much more of a culture shock than I thought it would be. Um,

[10:39]  I love San Francisco.

[10:41]  Yeah, it's wonderful. But, um, there are some different communication styles, uh, here than in New York. And, uh, I kind of joke that the first thing I learned was to not honk my horn um, as a form of conversation because that was not how it was done here. Um,

[11:00]  yeah, you New Yorkans, listen, I don't know what it is. I mean, it happens in Boston, too. Just the horn is always going. I'm like, what is that? Doesn't happen in Florida. I'm just saying that's you. If someone is beeping the horn at you, that's probably them cursing you out because you cut them off or something. But New Yorkans, it's just like the day everyday thing.

[11:17]  Yeah. It's a It's a conversation.

[11:24]  Yeah. And so coming to San Francisco, um I I was lucky enough to be at the same company in New York for 12 years. And uh I feel like that's so unusual in in our day. Um but I was looking for something similar and I found an amazing organization that was um supporting folks exiting homelessness and um got to work with amazing people and just truly amazing clients. Um and uh and then that chapter ended. Um and I found life moves. Um, and so I I get to say that I'm new to Silicon Valley, um, but I'm not new to the work and it's been really amazing to um, learn and bring, um, my expertise at the same time.

[12:17]  Hey, real quick, have you enjoyed the podcast? We first want to say thank you and we also just want to give you a little insight of what we're up to at Francis. Some don't even realize that we're working with organizations to help them use AI to create that real human communication experiences. Whether that's actually supporting your your families, those patients or the entire community, we're actually creating tech that connects. Check it out. Francis.ai.

[12:44]  And you're overseeing now like 40 programs if I'm not mistaken from our past conversations.

[12:48]  Yeah.

[12:49]  What are some of these programs consist of?

[12:52]  Yeah. So, we do um a lot of interim supportive housing and that's what we call uh our shelter programs and it it's intentional um because when folks think of shelter you kind of think of I don't know maybe three hots in a cot um and not a lot of safety and not necessarily a lot of services or support um and that um our work has evolved so are beyond that. Um, and we're really um proud and excited about our approach to serving folks who are unhoused. Um, so all of our new sites, we have uh over two dozen interim supportive housing sites from Daily City to San Jose. Um, so spanning two counties um and uh and lots of people Um, so all of our new uh builds include private uh rooms um and private bathrooms um and whatever possible at least basic cooking facilities. Um, and that is that is so powerful um, for someone coming in to be able to close their door, take a breath, take a shower um, you know, and and sleep and and have that security and and safety um, as as they start moving forward in their goals. Um so we do interim supportive housing but we also do a ton of wraparound services. We have children's service specialists to work with um our families with kids. Uh we do u mental health and behavioral health support. A lot of employment uh support. We have homeless prevention programs. Amazing um street outreach teams um throughout Sonteo County. Um, we also have some permanent housing programs, rapid rehousing. Um, it really is this uh kind of amazing um web of services.

[15:14]  It's almost like you you you get every level kind of checked off the box, right? From the the young kids to like you mental health, behavioral health, like you really touch all aspects of life if I would say. Um, and I like that. I like that. And then you've also mentioned the last time I spoke to you that you guys were implementing AI and really not to steal time but to save time. What are some of the things that you're also exploring in that field because there's not a lot of nonprofits that are kind of advanced in the space of technology especially something like AI. What are you guys doing over there?

[15:43]  Yeah. Yeah. So we are dipping our toes into the AI waters and I'm super excited about it. So, we're working with a consultant to build I'm not going to use the right words, but kind of build this AI universe that we get to populate with our um evidence-based practices like harm reduction and trauma informed care and strengthbased um uh care. um and then also include all of our contract requirements and our funer guidelines and um sometimes city ordinances. Um and so kind of throw throw all of this into one place and then say, "Hey, we need a policy on TV testing and we want it to be the same um to the greatest extent possible across our 40 programs, but we know that there were going to be some differences, too. So, let us know about that. And then the the goal, we're just in beta testing right now, is that it will give us the policy and the template that we feed it

[16:50]  um and it will get us about 80 or 90% of the way um to to great and then we use our staff or community experts to get us the rest of that way to 100%. But when we look across all of our programs of all of the policies and all of the different uh expectations um or rules or laws that we need to comply with, it could take staff years to to do this um in a way that we are building this AI tool um to do in hours um once we kind of get get it lifted up. So, super excited to harness something.

[17:38]  I love I love that you laughed when you said or kind of chuckled when you said feed it. That's exactly what you got to do. Got to feed it the data, you know? So, I can tell that you're an AI expert almost because you're talking the AI language like we got to feed the data into the system. So, yes. No, I love it. And it is true when you really use it for the good. Um realizing how much time it does save. There's so many things that just drives us crazy as an organization. is like if someone could just do these pieces, we can show up, you know, where we really want to show up and do more of the things that we really want to do. And it looks like you guys are finding the ways on how to do that. How do we continue to be on the front line and let the back end just kind of almost work on itself? Because that's where the fun part is, is where we get to really work with people. Um I don't want to be looking at papers and dealing with computers, you know, that's that's not the stuff you want to do. So, I hear you. I'm so happy that you guys are in that um process.

[18:28]  Yeah. What other things do you think that when you for the line of work that you guys do when AI is there anything else you've heard or or could even imagine where it could help out? I would love. So, so kind of as you you joked about, nobody loves documentation, right? Nobody almost nobody I think loves paperwork, right? But it but it is a really important part um of our work. And when we work with people, we need to we need to document that, right? We need to understand what we do. We need to understand the impact. We have an amazing impact and learning team um that digs into those more research and data focused questions. Um but we can only do a great analysis when we have great information, right? Um and so I would love to keep exploring a way that we can use um you know safe privacy protected notetakers um or other AI tools to do the documentation part um of what our staff are doing with our clients um to again preserve their time to do to do the work uh right the the the direct services that we're doing um and not write you know as many notes themselves. Um so that's something that I think uh you know is is starting to happen within the ecosystem right when I go to my doctor now she's like hey do you mind if I have this AI notetaker and I was like great you just get to focus on me yes

[20:03]  um so so that is uh another dream

[20:07]  when I speak to healthcare leaders that's one of the things I'm most surprised of is like what the experience is going to be so different when I go see my doctor you get to talk to me and look at me you know what I look like now. So many times, right? Right. They're just talking to you and you're here and they're just Mhm. Mhm. probably you leave the room, they don't know what hair color you had, what eye color, what shirt you had on cuz that's just how into these notes. So I love I do love even for the board meeting like when we have virtual meetings to have a notetaker in the room. Easy to take a transcript and says, "Hey, give us everything that we need to work on or you like it's just at in seconds." You know, I used to say the Amazon effect, but now it's like the chat GPT effect. like you get this instantly. Um, is it a good thing? Yes and no. Because now I feel like now people's expectations start to change, right? Because now they know that you can get things a little faster. Expectations change. But I'm I'm happy that you guys are really kind of dip into it. And you know, you're a leader that in reality you could stay in the clouds if you wanted to, but you keep your feet doing the frontline work as always. What does that why does that matter to you so much?

[21:09]  Yeah, it's so important. Um and and I think sometimes um maybe forgotten about a little bit, but for me um I can't I can't be the leader I aspire to be if I don't understand what my staff are experiencing in the

[21:31]  um right if I'm not sitting at the front desk and noticing that you know the the arm of the chair is like all torn apart um then like those are the things that sometimes times people are just like, "Well, this is the way it is, right?" And I'm like, "No, let's get you a good chair." Like, "Oh my god, we can do that."

[21:52]  Makes a difference.

[21:53]  Yeah. Yeah. Um and so, uh yeah, it's really important for me to understand that that reel, right? And

[22:03]  I don't think I can even simply just having a conversation with folks to be like, "What's top of mind? what you know, what do you wish you had a magic wand to change? I if if you're not like in the moment and experiencing it with them, then those opportunities um are easy to lose track of. Um and so for me, it's important to to do the doing with my staff. Um and uh and not just for show, right? But um when we opened our newest interimm supportive housing site in San Jose, um we were still ramping up our staff when we started welcoming clients. And so I got to do um an intake, which is what we we call intakes, welcomes, right? Just trying to be really accessible and um

[22:52]  yeah, mindful of our language. Um, and I I had no, you know, I knew the paperwork, but I hadn't done um a welcome with a client before. And so I was like trying to set up the room and making sure there was like water and that like our seating was felt comfortable and I wasn't being overwhelming. And you know, then I I met the client and I was like, "Hey, this is my first time doing a welcome. Just you know, if I'm like a little clunky, I apologize in advance." and he was like, "Okay, like we got this." And I it's just so so sweet and thoughtful. And you know, it was a moment where we ask all the things we have to ask and we go through the rules and like we we work to do it in as open and transparent and like not threatening way as we can. But when I think about what I asked that person to share with me, um their experiences, their um diagnosis, their you know history, we had just met, right? And so it was such um really a reminder of if I'm not real and I'm not offering um if I'm not showing that I am trustworthy and that I'm not actively trying to create a safe space, how could I ever expect somebody who just met me to be able to share their real and it's a situation where I have all of the power and they have none. time, right? I'm like holding this

[24:30]  safe housing opportunity in my hands

[24:33]  um and just really um trying to honor that um and and earn their trust, right? To to not take any of that for granted. Um and it was through that experience that um this client uh shared that he has a 10-year-old daughter. Um and he was asking, you know, could she visit him? and we're kind of going through this is an adult only site that she can, you know, kind of see the space from the parking lot. And he was like, "No, it's good." He's like, "It's he he said, I can't wait to tell her that I'm going to be in a safe place, that she doesn't have to worry about me being on the street."

[25:13]  Wow. Um, and just recognizing not only is this opportunity changing the the dayto-day reality of this client, but also impacting all of his loved ones. Um, just you don't necessarily see that.

[25:33]  Yeah. Yeah. Yeah. So very involved in in not just one person's life, but in in everybody's life, right? people that that just kind of need that reset, that restart um that you guys are part of that. I I ask for leadership thoughts when you think about things that you did not learn in a boardroom or in a classroom cuz your leadership style is very different and I love it. But what are some of the things that you felt that you did not learn actually in a boardroom or in a classroom that you truly just still instill in others and share with others?

[26:06]  Um absolutely. So, I hope that this has changed since I've been in a classroom. But, um, just being able to make mistakes and seeing mistakes as a sign of strength and not as a sign of weakness. That was something that was never talked about. And again, it kind of like felt like I always had to be perfect and that there was one right way to do things. And now I'm like, there are so many ways to do things and they all have shades of right in them, right? So, so what is what is my approach and how can I keep checking in with folks if if my approach is working for them um right to like have that as as a true partnership um and understanding. I also wish I think it's kind of connected but I wish I somebody told me that people in powerful positions right with titles with money they're just people like there's right like there's uh they're not necessarily any different and so like they're not on a pedestal. You don't need to put them on a pedestal. Just be real um and respectful, right? and all of that good stuff. But I think I felt um like, oh, they're they're just different in this like magical unicorn way. And

[27:33]  um I don't think that's true.

[27:35]  You're right. I think that from young ages thinking of if you don't get an A, then are you really good enough? Right. You didn't get a 100. So that means you you didn't do well. You only got a 89. H you could do better. It's like so it's like they want you to always be at 100 and it's not always the case. That's that's not true. And and just continue to show up if if that's how I look at it. Continue to show up. You know, you'll continue to learn. Opportunities will present themselves. And I don't know that we've had those conversations enough as we're in the school system as well. So now I you are right. It's they should teach that it's okay to get a C. Hey, this maybe maybe next time you get a B. It's good, you know. But so I mean especially I think our parents I think about my you know my my mom was probably lenient but there's parents that you didn't get an A like what do you mean you know so it's also at home as well I feel like it's a little bit of both but it goes back to just how we're kind of taught these things for so long and they really were never right then it creates so much anxiety and depression and all these different things and that's a whole another conversation. Okay, we we could go down that we're not going to go down there. No, I I uh I appreciate I appreciate this conversation because it has truly um share gems for other leaders. We're in a space where, you know, the country is living in in a like what do I supposed to do? But when they get to hear raw conversations like this, it's like listen, you're not alone in some of these conversations, right? We we all have great programs, but I'm pretty sure there's also those times it's like, oh my god, these programs could be cut, you know, as well. Um where do you guys when we when we think about today's society in the space do you feel that AI could help going back to AI you think it can help in the space you know because a lot of people it's like we have to start to cut things but I think this is a great time where tools and these resources could be to our benefit like for those that are maybe not involved into AI what is your message to them because I think there's also fear around the word AI um people scared of it but it's been around for a very long time. What What are your thoughts and what are the words you say to people that may be in that space of just fear

[29:43]  understand what they're afraid of, right? Like um is it around replacing jobs? Is it around um not controlling private information? Like is it I could be many many different things, right? So understanding what is what is at the heart of that fear um and then uh is it is that fear based in reality right like what are the chances of that um actually coming true and I know for for us the ways that I think of harnessing AI it won't be replacing people but it will be um creating more time hopefully for us to do the work that AI can't do, right? All of that human touch and understanding. And so how can I especially in times where often nonprofits are being asked to do more but without more resources um for us to keep getting savvier around preserving our staff to do the work that um must be done and only they can do and kind of um yeah easing that administrative burden um that we also need to comply with. that uh we can do a little different.

[31:06]  Okay. And I What's the heart and hustle um in your leadership today? Like how do you keep those both alive?

[31:14]  Yeah. Yeah. So um I think one of the ways that I do it is I keep thinking about what I'm doing, how I'm doing it, and is it working? Right? So, one of the things I've started doing is uh what I call my Monday message. And I wear a social justice work appropriate t-shirt every Monday. I have like a whole little collection of them at this point. Um and my 5-year-old helps me like pick out which one to wear. Um and and it's my way of showing like an act of resistance um in in that moment. um showing uh my staff and everyone who sees me uh where I stand on things that um I am someone who's safe uh and an ally for them. Um and uh if I can start a conversation or start someone thinking um that to me is kind of connecting both that heart and hustle um in our world.

[32:22]  Love that. I love that. I love also that you have this 5-year-old that is so involved into that, right? like you're you're teaching her so many good things already. She doesn't even know it yet, but she's going to take all these skills and everything that mom has taught her and the things she was able to see and implement it in life. Um, and I think it's always cool because it's not really about us, you know, it's about those that come after us, whether it's our kids, whether it's other young leaders, whether it's those that, you know, we touch like you mentioned in the conversation because there's so been so many times as you mentioned, I'll wear a shirt that says know your worth, right? And people would just like I was one time I remember going to a restaurant and I walk in just to pick up my food and he's like yeah I know my worth and I just starts yelling and I'm like yes I love it right because it allows people to go back into these moments that sometimes they wouldn't think you know and and for someone as bold as you to just you know kind of wear it on their their chest. Um I love that as well. I wear this shirt that says adopted. I was adopted so I wear it you know proudly. It says adopted on it and and my my neighbor says man I love your shirt. I love that you just walk around saying that you're adopted. I was like cuz this is a conversation starter. There's so many of us and and when you it's almost like when you find out someone else is adopted, it's almost like this long lost brother sister like, "Oh, you're adopted, too? That's so cool." But when I was young, it was something that was not cool, right? But it is actually pretty cool when you think about it. So, I love that you do that and it is a conversation start and it makes people's day, you know, just doing things like that. Listen, we have to start uh start to wrap things up here. But when we think about where can we follow um what you guys are doing, not just the organization, but also if we can mention your LinkedIn, like I'm pretty sure you're on LinkedIn. I don't know if you're active on there, but we want to be able to follow you. We want to be able to follow the organization and look at those resources. What does that look like? What is what those usernames and URLs?

[34:04]  Yeah, absolutely. So, uh lifoveves is lifove.org. All one word, nothing fancy or hard. Um, and I'm on I am on LinkedIn at I'm not Leonard. Um, and so you can search me and uh love to connect with folks. Um, and just um, you know, whether we're kind of in your backyard or if there are other nonprofits, this is a time just to to connect. If you have a question, if you're not really sure, um if you're wondering how to get involved or what even being involved could look like, um this is a great time to kind of lean in and be curious. Um and uh and sometimes it's as simple as giving a smile to someone you pass on the street.

[34:56]  Julie is you ready to be in the house seat? I have a great question from my last leader me um from livewell actually livewell.org so if you guys want to take that out for those that are listening but I have a great blind question. You ready?

[35:09]  Yes.

[35:10]  What's one value or belief you lead with now that would have surprised your younger self?

[35:25]  I think it was gonna be a good one. It's it's a it's a value of our you shared with this which is the authenticity. I think um like I went to social work school, right? We I feel like we just talked about boundaries all the time. Like have this wall, don't reveal yourself. Don't overshare. Like it's about them, not you. And and that is true. But I don't know if it was my interpretation, but woo, those walls went high and thick. And it took me a long time to understand that if I wasn't letting my true self out, then I couldn't let other people's true self in, right? That it worked both ways. Um, and that's something that's something I wish I had known earlier and I think my younger self would be a surprise.

[36:12]  Okay. And what is your blank question to the next leader we have here on the Heart Hustle?

[36:16]  Yes. Um what is a a challenging uh risky um step you took or decision you made and why um how did you approach that decision and looking back on it what do you think?

[36:32]  That's a good question because you know people don't take enough risks so I would love to know what those risks are. Okay. Okay guys, this has been such a great conversation with Anad and all we ask is that you guys do the small things that truly make a difference. Like, share, subscribe, let people know that these organizations do exist, that there's leaders out there that are truly making a difference in our world and not asking for a paycheck, asking um to just give back, you know, doing it out of purpose because they truly love what they do. This is not it doesn't feel like work. Every time I speak to another leader, I'm always just so impressed on how people say, "Man, I love this. I'm so happy." Sometimes I hear I should have done this sooner. Um because it does definitely fill our cup. So whether it's volunteering, whether it's donating um you know money, whatever it may look like, just just start somewhere. Liking, subscribe, and commenting. My name is Ephrain. This has been a we'll catch you guys on the next one. Lers.