Overview
Molly Graham speaks with Kaya Henderson, former chancellor of DC Public Schools, about leading change in a public system where families, teachers, unions, politicians, and communities all have strong and often conflicting views. Henderson describes how DCPS moved from long-term decline to sustained improvement by setting clear priorities, involving affected people in decisions, and explaining tradeoffs plainly.
She also discusses her current work at the Aspen Institute's Center for Rising Generations, where young people are helping shape programs intended for them.
Key Takeaways
Start with a manageable set of public commitments. Henderson's team set a five-year plan with a small number of goals, including stronger academic results, improvement in the lowest-performing schools, higher graduation rates, and student satisfaction. The point was not to promise instant results, but to give people a shared definition of progress and a realistic timeline.
Major reforms should be iterative. DCPS began with a focus on hiring and retaining strong educators, then learned from teachers that the district also needed aligned expectations for instruction, a common curriculum, and better professional development. Each fix exposed the next problem. Henderson argues that connected reforms compound over time.
People closest to a problem often hold information leaders lack. Community members reviewing proposed school closures pointed out that district maps showed a bridge that no longer existed. Teachers explained that they were receiving conflicting signals from curricula, evaluations, and school leaders. Henderson's role was to combine institutional data with lived experience rather than treating either as sufficient on its own.
Listening does not mean adopting every request. It means showing people what was heard and being candid about what will happen, what may happen later, and what cannot happen. DCPS publicly classified feedback on school closures as green, yellow, or red, with explanations for rejected ideas. Henderson says people can accept hard decisions when they understand the constraints.
Conflict becomes more productive when participants share a purpose. In union negotiations, Henderson changed the setup from opposing tables to a circle and asked everyone to begin by talking about a student who mattered to them. That reminder helped shift the discussion from institutional combat toward a shared responsibility for children.
Young people want partnership across generations. In listening sessions with about a thousand young people and youth-serving organizations, Henderson heard that they want access to mentors, training, internships, and peers who share their interests. They also rejected the idea that adults should simply step aside. As one young colleague put it, solutions sit "at the intersection of wisdom and imagination."
Practical Steps
Publish a short list of priorities, a timeline, and indicators people can track. State what progress should look like before asking others to trust the process.
Before finalizing a decision, present it as a proposal to the people affected. Ask them to test the assumptions, flag missing facts, and suggest alternatives.
Build a public feedback log for contentious work. Categorize suggestions into: acting now, possible later, and not feasible. Give a direct reason for each decision.
Put stakeholders in the same room long enough to work through tradeoffs together. Include people whose interests differ, not only supporters or technical experts.
In difficult negotiations, begin with the shared mission. Ask participants to describe who benefits if the work succeeds, then return to that purpose when discussions become adversarial.
Define your own leadership approach instead of copying a model that conflicts with your values or strengths. Henderson's advice is to identify what matters to you, communicate it clearly, and lead accordingly.
Notable Quotes
"People are reasonable. They're crazy because we don't give them the information. We treat them like children." - Kaya Henderson
"Every time we invited the people closest to the problem to create the solution with us, we got a better solution." - Kaya Henderson
"The solutions that we seek lie at the intersection of wisdom and imagination." - Kaya Henderson, quoting a young colleague
Full Transcript
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Again, people are reasonable. We act like people are so crazy. They're not. They're crazy because we don't give them the information. We treat them like children. We don't see them as real partners. And so when you tell somebody, I mean, I can't do that this month because it's not in our budget, and people are like, Oh, okay. It's quite reasonable. The most interesting leadership lessons I've encountered have come from people who have actually had to create change. People who have spent years trying to improve complicated systems. People who have had to make difficult decisions when there was no obvious right answer. One of the things I love about making work life is that I get to introduce you to some of these leaders, people with extraordinary experience and hard-earned wisdom who often haven't had the time or interest to write a book about it. Today's guest is one of those people. Kaya Henderson spent years leading the District of Columbia public schools. When she took over, it was one of the lowest-performing school districts in the United States. The system had been through years of controversy and intense reform efforts. The scrutiny was relentless. Parents cared deeply. Teachers cared deeply. Politicians cared deeply. And they often disagreed about what should happen next. Every decision seemed to make one group hopeful and the other group angry. Yet somehow, under Kaya's leadership, DC public schools went from being one of the lowest-performing urban school districts to one of the fastest improving in the United States. Graduation rates rose dramatically. Enrollment grew after years of decline. And the district posted some of the largest academic gains in the nation. But that's the part of the story that's easy to tell. The harder question is how. How do you create change when people don't even agree on the problem? How do you decide whose perspective should shape your decisions? And how do you know when disagreement is a signal to change course or simply the cost of leading through something complicated? I've known Kaya for years, and one of the things that I've always admired about her is that she doesn't start with answers. She starts by trying to understand how a problem looks from the perspective of the people living closest to it: students, teachers, families, communities. So today, I want to talk to her about what it actually takes to improve a system when the stakes are high and everyone has big feelings and big opinions. I'm Molly Graham, and this is WorkLife, where we untangle the messy human side of work. Let's get into it. Okay, so first, let me say with great joy, Kaya Henderson, welcome to WorkLife. Thank you. I'm so happy to be here. So you took over as Chancellor of DC Public Schools in 2010, and the district at the time was one of the lowest performing in the country. For people who don't follow education, will you just paint a picture for us? Like, first of all, what is the job of a chancellor? And second of all, what was the situation that you inherited? So most people know what a school superintendent does. Chancellor is just a different name for superintendent. And so I was responsible for, at the time, about 140 schools serving about 60% of the students in Washington, DC. I got there in 2007 as the deputy chancellor under Michelle Rhee and worked for three and a half years under her. And then when she left, I was appointed chancellor. And the district that we inherited was one that had been in a freefall. It was in a death spiral. We were the lowest performing urban school district in the country. We had been in a 40-year enrollment decline, 40 consecutive years of enrollment decline. We were spending money in places that we shouldn't have been. We had 29 different data systems, none of which talked to each other. So, of course, we were paying people who were no longer alive and all kinds of crazy things, and not paying the people who were alive and those kinds of things. Our graduation rate was under 50%, so we were graduating less than half of the kids who were coming through our schools. I mean, our teachers, we were hemorrhaging teachers, you name it. Like every terrible indicator was our reality. And I'm proud to say that when I left in 2016, we were the fastest-performing urban school district in the country. I'm super proud that 10 years later, we are number one in the country for post-pandemic recovery, both in math and reading. Graduation rates are up to 75%, and we had six consecutive years of enrollment growth, so people coming back to the school district, and that has continued since I left. So overall, I mean, we did some hard work, but it was good work. Well, this is what I want to talk to you about today because, I mean, so, so many people would look at a problem like that and think it's unsolvable. And you, and obviously lots of people around you, made a difference, a huge difference, and not just a short-term difference, like a long-term difference, as you just said, like a sustained difference. So I really want to talk today just about how you did that, you know? And one thing that struck me as I was thinking about talking to you today is that I think you were surrounded by constituents who cared, right? Everybody cared, like parents and teachers and unions and politicians and community leaders. But I think so many people wanted very different things, like, or thought the problem was, you know, something different. Yeah. What was interesting is part of the way we were able to garner enough political support and cover was that, like, we were at rock bottom and people were like, just do anything, like, just do anything. And so everybody was just desperate for something to happen. So that was good for us. But then, of course, every single one of those constituents had a different idea of what we should be doing, how quickly it should happen. And we didn't have clear measures of success. So even if we, like, hit one goal, people would be like, well, what about the other 17? You're like, well, wait a minute, this was a big one, and we should— So what I found was it was really important to frame out for people what they could expect, when they could expect it, and chart a steady, sort of steady indicators of progress, because everybody had different ideas of what should be happening when. What I mean by that is, you know, I would say to people all the time, here's what's going to happen over the next five years. Over the next five years, we're going to do five things: one, two, three, four, five. We call that a capital commitment. It was our strategic plan. And anybody who was in the district at that moment could tell you what those five things were, right? They were raise our test scores. They were improve more significantly in our 40 lowest-performing schools. They were increase our graduation rate. It was 90% of kids will be satisfied, will like their school. And I can't remember the fifth one, but it'll come to me in a minute. I mean, it's impressive that you remember four 10 years later or so. Right. And so the idea was, you know, this is what we can accomplish in five years. It's going to take us five years to accomplish this. It's not going to be a straight line up, but in year five, I guarantee that we will hit these five goals, right? And that helped people sort of recalibrate what they could expect. A school system is the most complicated organization. I mean, think about a food service organization, a transportation organization, a facilities organization, a teaching and learning organization, a healthcare organization, all in one, right? A community advocacy organization, a political organization, all of these things in one. And all of these things are deeply interconnected. And so important to help your stakeholders understand what you're doing, what you're not doing. A lot of how we managed sort of public opinion was by explaining to people. We'd invite people in to co-create with us. I would always say, These are not my schools. These are our schools. So we're going to make big hard decisions together. So when we had to close schools, instead of us making the best decision with the information that we had, I would say to my team, Come up with a proposal for which schools we should close and why. And then we're going to take that proposal to the community. I didn't ask you for a plan. I asked you for a proposal. We're going to take that proposal to the community. We have data. The community also has data. We're going to put those two things together and come up with the best answer. And when the community looked at the data that we had, sometimes they would be like, Oh my gosh, yeah, we have to close this school because, you know, the resources are not actually getting to the kids because we're wasting them on buildings or whatever, whatever. Other times the community would say, You can't close this school because... You know, there is, it's a two-mile walk from here to there. And my team would say, Oh no, the kids could go right over the bridge, and it's a half a mile walk. And the community would say, That bridge was obliterated two years ago. It doesn't even exist anymore. How is that still on your map? And so what would happen is we always came to better solutions with the community, but the community also understood that, like, sometimes we were making just the best of a non-ideal decision. And I think by bringing people into that process and explaining to them why we can't do the thing that you want to do, or showing them the data around why we can't do whatever you're demanding, people are reasonable. People understand. And I think we have to stop treating constituents like we have to chew things up and spit them out for them. They can come into this complexity with us if we truly value their input. I want to set the stage in one other way, which I think is really important, which is you obviously took over from Michelle Rhee, who became very famous for some big fights. And you've actually described her as a fighter. And you've also said that, like, in past interviews, that that was what the district needed first. They needed a fighter. I'm curious what you, like, when you said yes to this job, which I know you declined a couple times, like, what did you think that the district needed next? Was it that partnership, or, like, how did you think about that? I am a student of Latin American revolutions, and there is a cycle to revolutions, right? And first there is, you know, dissent and unrest with the status quo, and it boils over and breaks out into usually violence, political violence. And over time, like, people get tired of the violence, tired of people being disappeared and all of those things. And you have to sort of calm everything down and begin nation building or the institutionalization of the values of the revolution, right? And that's how cycles flow. And if you are successful in that institutionalization, then things are cool for a long time until there's dissent and unrest again and whatnot. And we see that happening in Latin American history over and over again. And I think a little bit around that cycle, I think, you know, Michelle's time represented real dissent and dissatisfaction with the status quo. We had to break the existing systems. But we were all, like, teachers were tired of fighting, families were tired of fighting, and I felt like part of my role was to bring calm to the situation, but also to begin to institutionalize. Some of the ideals that we were fighting for in the revolutionary phase, right? And so my job, my role as a leader in that phase of the organization's development was to really bring down the temperature, help people understand that, like, together we could actually make amazing things happen and institutionalize some of the things that we were fighting for. And I, you know, one point of pride is we created and instituted one of the most robust teacher evaluation systems in the country with a pay-for-performance piece attached to it so that our teachers don't have to have second jobs and whatnot. They make really good money, especially if they're amazing with kids. It's performance-based. And we put it in place in 2008, and it's now 2026, and it's still in place. And this is what I mean when I say institutionalization of the ideals of the revolution. I love—first of all, I did not know that you studied Latin American revolutions, but I think it's also such an interesting parallel for, you know, sort of an institutionalized death spiral and what needs to happen in order to truly change it, which is, I mean, I think to your point, it sort of had to get broken and then rebuilt. And in some ways, yeah, Michelle did the breaking or the breaking of the cycle, and then— Or the breaking of the cycle, and then your job was to come in and rebuild. Yes. So you talked about your five-point plan, and one of the things I love about what you talk about is just the fact that anyone, you know, in the district could repeat it, that everybody knew it, because I think memorability is such an important part of sort of sustained and effective leadership. But will you talk about, like, did you walk in with that plan? Like, I know you'd been working with Michelle, but, like, how did you kind of, like, know where to start and decide what was most important? Yeah, that's a great question. So when we came in, we had one theory of action, and that was get great people. And so as we got there and started talking to teachers and principals and central office staff, there was a real problem around human capital. A lot of it was quite technical: human resources stuff, data systems stuff, you know, union contract stuff. And as we started to work on those things, what became clear was, you know, teachers, for example, were like, Listen, we don't know what you want us to do because our diagnostics say one thing, our curriculum says another thing, our evaluation says another thing, our principals say they want—we need some alignment. Just tell us how you want us to teach, and then we can do that. And so we created the teaching and learning framework, which helped people understand where they were against our expectations for teaching. Then teachers said to us, Okay, okay, we get how you want us to teach, but let's talk about what we're teaching, because we didn't have a standardized curriculum across the district. So what that meant, that what third graders were learning in school on one side of town might be radically different than what students were learning. On another side of town. And so in response to that, we worked on a standardized curriculum. Now, because we had these human capital systems in place, we knew who our best teachers were. And so we could say, let's pull together our best first, second, third, fourth, fifth grade teachers. Let's also bring in parents. Let's bring in content specialists, and let's have them work together to create a curriculum that's aligned to the standards. We also wanted to embody rigor and joy because those were two values that were very important to us. We want kids to be happy, and we want kids to be, you know, to have content that is worthy of their time and attention, no more of this drill-and-kill stuff like, we can do better for kids. And together, they put together a curriculum that people are still using. It's outstanding and is part of the reason why we, you know, made such substantial gains. And then folks were like, okay, it's great that we know what we're teaching, but we don't know exactly, like, this is much more than we've ever been asked to teach before. We need different professional development. And so we have to redesign our professional development system. I say all of this to say it was an iterative process, right? We went in with one idea of something that needed to be fixed, and it did, but that sort of pulled back layers of the onion that also needed to be fixed. And so we were able to, in an iterative way, stitch together a series of strategies that were complementary and compounding to help us get to what we wanted to accomplish. And then the second lesson that I learned is every time we invited the people closest to the problem to create the solution with us, we got a better solution. You know, I'd say to my team all the time, we're smart, we're cute, we got degrees and PowerPoints and Excel, but, like, those people who are closest to the problem actually know what to do. They just don't have power, they don't have the voice, they don't have the invitation to sit at the table. And so let's put these things together. 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And in that role, we were sort of drilled with the idea that the single most important in-school factor for moving student achievement is the quality of the teacher. And so I feel like I came into the teaching profession understanding that the most important thing that we could do was focus on teacher quality. And I came into school districts, New York City, Washington, D.C., that were focusing on everything except teacher quality, right? They were focusing on buildings. They were focusing on, you know, these whole school transformational models and all of those things. But nobody was ever asking about teachers and were we getting our—were we keeping the best ones and none of these things. And as a teacher, I experienced the kind of neglect, I would say, administrative neglect, where teachers would come together and be like, Okay, we should do this cool thing. And, you know, a lot of times the principals or the assistant principals would be like, No, we're not doing that. You're like, But why not? This is good. It's, like, sound and okay. So I experienced, you know, having real ideas about how to move student achievement as a teacher and not feeling listened to. And then I just watched—I mean, I just don't—there is no other industry where management doesn't listen to its employees and expects great things to happen. And so one of the first things that we did when we got there was set up teacher focus groups. We did hundreds of focus groups, twice a week, Tuesdays and Thursday afternoons, just meeting with teachers to say, What's going on? What's wrong? What would make your life easier? How can we help? And that's where they said, Look, you need to tell us, like, how you want us to teach, and all of those other conversations were subsequent from that. And what I found is every time we listened to teachers, like— Good things happened. And I think part of this comes out of the fact that I'm not a career—I am a career educator, but I am not a traditional, I didn't go from teacher to assistant principal to principal to district administrator to whatever, whatever, right? Like, I didn't come up and through the system. I was a teacher for two years, and then I went and did lots of other things in education. But it meant that I didn't feel like an educational expert. So I didn't have pride of ownership. I didn't have, like, this is the idea to fix the school system, and so you need to come with me. In fact, in the Western world, I feel like we teach leaders, like, what is your vision? People kept saying to me, What is your vision for the school system? I don't know. I want it to be good, right? Well, how are you going to get it? I don't know. And I'm going to engage people. Like, we say leaders should have a vision, and then they invest people in their vision and bring people along. I couldn't do that. I had to say, who are the best people on all of these topics? How do I bring them together? And sometimes the best people are not just people with credentials; they are people in the community. How do I create opportunities for the best people to work together to co-own this problem and co-own these solutions with me? And I think that's a very different leadership approach. One of my proudest moments was as I was leaving, right before I left the district, there was a mayoral election, and it coincided with a citywide revision of our boundaries and feeder patterns, which, you know, could create civil war when you start drawing lines. People buy houses based on what school boundary they're in. The boundaries hadn't been changed since 1967. You can imagine that in 2015, it was a very different situation. And superintendents have been kicking the can on this because they didn't want to anger people. But we had a system that was just filled with—we were jury-rigging all of these, like, weird workarounds, and we needed to just make the systems change. And we put together a group of people, a task force of people from all wards of the city to figure this out. And this task force, people got on it because they wanted to sort of protect their own thing, right? But what happens when you start to work with other people is you realize that, like, you all are doing this hard work together. I can't shank you, right? Because I sit at the table all the time with you, and we've developed a rapport, and we talk about our kids. So I got to find a solution that actually works for both of us, right? And so these people actually worked really hard, and they came up with, like, the best of a set of non-ideal decisions. And I was like, great, present it to the community, right? This would have been my job, but why not, right? Everybody wants to be in charge. Let's go. So they presented to the community, and literally the community was like, We hate this. Bah, threw tomatoes at it. It was terrible. And then people were like, Oh my God. And I was like, Welcome to my world. But all this means is we have to go back and we have to figure out the next thing. And so they took another pass at it, listening to what their neighbors and advocates had said. They went back, they rebuilt the plan, and the plan was incredibly good, and they released it. And the sitting mayor said he would take the recommendations. And there were three candidates in the mayoral race who were all representing constituencies who they felt didn't get what they wanted or what have you. And The Washington Post did a poll and asked, you know, community members, Would you vote for a candidate who would throw out the Boundary and Feeder Commission recommendations? And people resoundingly said, We would not vote for a candidate who throws out these recommendations. These recommendations were from the community. This is, you know, we've all been engaged in this process, and— It actually changed some of the mayoral candidates' position. And for me, that was, that went to show that, like, the community owned these schools, and they weren't going to tolerate a leader who came in and said, later for the process that you just went through, or later for, you know, all of this work that you did. They wanted somebody who was going to respect their hard work and what they had come together to do as a community. And I was proud. I was incredibly proud that the community, you know, worked to take on this really difficult thing that could have ripped our city apart, but it in fact brought our city together because the people closest to the problems had to work together across lines of difference. We didn't just have DCPS families, we had charter school families. Like, these all, all of these belong to us, and so let's figure out the hard stuff together. Okay. I love this because your themes of just like this deep partnership and deep listening are, you know, are coming through so strongly. And I think if I was sitting, you know, confronted with a broken problem like the one you had and I had to lead through it, one of the questions I would have is, listening sounds great, but sometimes when you listen to people, they just assume that then you're going to do what they said, you know? And you did these, like, very broad listening tours. I mean, you're talking about Hopes and Dreams where you had, you know, boxes all over the city and every opinion, every, took in every opinion and, you know, very broad listening. So, like, how did you actually, A, decide what to listen to amidst all of that? And B, like, kind of how did you handle when you're then saying, thank you for all your input, like, here's what we're doing, and you know some people are going to be pissed off. Yes, absolutely. So important to communicate what you heard, what you're doing, and what you're not doing. So, for example, when we did the Hopes and Dreams campaign, we basically, I mean, imagine 10,000 sticky notes, right? And you group them into the big things, and then, and for the most part, The vast majority of them fit into big themes. Some of them didn't. And we then just, when we sort of laid out the plan, we said, here are the other things that we heard from people. And sometimes it was, we can't do this in this first five years, but it is something that we can do later on. Sometimes it was, we just won't have the money to do that. Like, that's really expensive. And so important to acknowledge what you're not doing. And then I think that, you know, and sometimes you have to get really granular. So I think about, we did school closings in 2013. And we had a website up called Engage DCPS where people could give all of the suggestions that they wanted around the school closings process. And what we did, I mean, this would have been so much easier if we had AI. But what I did was I tasked my team with listing every single suggestion that we got and putting a green, yellow, or red designation next to it. Green meant we were doing it. Yellow meant we can't do it right now, but we may be able to do it later on. Red was we can't do it, and here's why. And so if you were able to pull up that website these days, you would see a written explanation for why we weren't doing all of the red things. And people are like, Oh, okay. Like, again, people are reasonable. We act like people are so crazy. They're crazy because we don't give them the information. We treat them like children. We don't see them as real partners. And so when you tell somebody, I mean, I can't do that this month because it's not in our budget, but, like, I do think that after we rearrange this, we might be able to get to it later. Or, We're not going to do that because research shows that there's not a good return on investment for that and blah, blah, blah. Sounds like a good idea, but research says not. And people are like, Oh, okay. It's quite reasonable. We got to get away from this whole, like, we're the experts. Drop your kids off in kindergarten and we'll turn them out in the 12th grade and they'll be ready. That's how educators have thought for decades. And the truth of the matter is that doesn't work. It hasn't worked. And so let's figure out how to work together. But part of that means assuming the best about people, about teachers, about union people, about, you know, community advocates, about administrators. I'll never forget my first—sorry, you just got me on a roll, but I have to say this, like— The first time we did a union contract negotiation, which was one of my first tasks when I got here as deputy chancellor, the contract was expired. People were, you know, screaming and hollering. And so the union said, All right, let's set up negotiations. And I said, Okay, fine. And I've never negotiated anything in my life before. I took a negotiations class in graduate school, but that was it. And so they were like, Okay, and like the room was set up with like two tables, and we're supposed to be on one side and they're supposed to be on the other side. And I was like, This doesn't make sense to me. Why don't we sit in a circle? And they're like, Why would we sit in a circle? And I was like, So we could all see each other and we feel a little bit different than whatever. And they're like, That's not how we do. And I was like, Well, that's what we're going to do today, right? And so we sit in a circle, and I'm like, Let's start with us all talking about a kid who made a difference in our lives, right? And they were like, That's not how we do negotiations. And I was like, But why not? Like, that's what we're here for, right? Like, yes, we're going to negotiate a contract, but like, this is all about kids. So let's all go around and talk about a kid, right? So we do, and— These people were like, Huh, we didn't know that. Like, everybody on my team is a former teacher, right? We're administrators now. We're all former teachers. We're all, like, people with hearts. And they were like, Huh, we didn't know that you were teachers or that you, like, had kids in your lives who would... And I'm like, Who? Like, did you think that we got cranked out of the, like, you know, school district bureaucrat machine? Like, what is going on here? But I think that because we don't, like, center the crux of the work, like, our purest stakeholders are students. And so if everything is not grounded in students, then you get into these silly adult fights. And by grounding the union, you know, negotiations in kids, then we were able to say, Oh, like, okay, help me understand why you are trying for that, and help me understand how you think that's going to help kids. And so that gets to relationship. And so that allowed us then to create the most groundbreaking union contract in teacher contract history, right? But you have to be at a place where you can assume the best about each other, because that's what it takes to get to amazing solutions. I mean, first of all, I love that story. One of the things I heard you say is sort of like, you have to show people what they have in common, you know, and that if people understand each other, they're way less likely to shank each other or just, like, be only there for their self-interest, you know? I mean, so much of what I hear you saying is, like, partnership, like a real deep partnership. It is. I mean, it is this idea that, like, you alone, a leader alone is not going to, like, save anything or create anything or whatever. Everything that you do takes teamwork. And sometimes your team is the people you hire. Oftentimes your team is that set of people plus a bunch of other people. And, you know, I think it is Kennedy who said, you know, like, Failure is an orphan, but success has many parents. And I think that that's it. Like, you know, my job as a leader is when we fail, it's my fault. When we win, it's everybody's win. And that, you know, people are willing to, like, people want to be part of a winning team. And there's easy ways to do that. So why not? This episode is brought to you by Bill, the intelligent finance platform that helps businesses and accounting firms scale with proven results. With AI-powered automation, Bill removes the busy work from your accounts payable workflow. 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So, first of all, I want to say that how I started this work was we just went out and talked to a thousand young people and youth-serving organizations to say, What could a center like this do? And they said things like, first of all, you have to shift the narrative about us. You can't tell us that we are the leaders of today and tomorrow while at the same time telling us how lonely we are, how anxious we are, how lazy we are, how social media is melting our brain, how, you know, we don't value community and connection and belonging and all of these things. I was like, Okay, that makes a ton of sense. They said things like, you know, we want to be connected to opportunities. We just don't know how. And so help connect us to mentors, help connect us to training opportunities and internships and places where we can learn and grow. They also said, help us find our tribes. Like, we want to be with the people who care about the things that we want to be with. They said, you know, many of us are not waiting to lead. We're not waiting for somebody to say you're a leader. We're doing stuff in our communities now. Help show that to the world. And a lot of that—oh, and maybe the most important thing that they said was... We want to do this with the other generations. And that perhaps was the most surprising thing to me, because I feel like adults get a steady diet of, youth just want you to, like, you've already messed it up, just turn it over to them and they'll figure it out. And that's not what I heard young people saying. One of my young people who works for me says all the time, she says, Kaya, the solutions that we seek lie at the intersection of wisdom and imagination. And I said, Am I wisdom and you're imagination? And she said, Yes. She said, But look, she said, wisdom can't do it by itself and imagination can't do it by itself. And to me, that reinforces my sort of co-creation thing or the intergenerational thing where, you know, when young people and other generations are working on solutions together, we really get the best. And so for me, that meant, you know, out of a team of 10 employees, six of them were young people under 25 who we hired because I haven't been 14 to 24 in a long time, and I want those young people driving the work that we're doing. And so we have an associates program where they come on for a year, they get a full salary and benefits, and they work in the office with us. It's no remote, no dial-in. We are in the office three days a week because not only are they contributing to ensuring that what we're creating for young people is amazing, we are also building them as leaders. So I have the best job in America right now because every day I am in conversation with, in communication with amazing young people. Who are, like, tackling the most strident problems in our community right now. And, you know, the rest of the world could be going to hell in a handbasket. I don't know, because I am focused on helping these young people do what they do. You're in your happy bubble. Okay, I have one last question for you. Okay. So we had dinner a couple years ago, and you asked me, or the table, this question around what we wanted our legacy to be. And I remember sort of being, like, floored a little bit by the question because I had never really thought about it that way. And I want to kind of ask you a similar question, which is, like, when you think about the Kaya legacy, if there's sort of, like, one lesson or one belief that you hope outlives your career, what do you want that to be? I hope that my model of leadership, that other people find it useful. And what I would characterize as the hallmarks of the Kaya Henderson leadership way are love, authenticity, believing the best about people, especially young people, and this co-creation thing. I feel like that is sort of the cocktail that makes me me. And I hope that that allows other people to not lead the way they've seen, you know, others lead if that doesn't work for them. One of the most important things that, one of the most important pieces of advice that I've ever gotten, I got from David Coleman, who runs the College Board. And when I was saying no to the chancellorship 50 times, he said, Why don't you want to do this job? And I said, Because I don't want to, like, go to community meetings and have people screaming at me, and I don't want to, you know, like, I don't want to do all of these things that I watch superintendents do that I actually don't think is useful. And he said, But why would you do it that way? Like, why wouldn't you just do it the Kaya Henderson way? Like, if you don't want to go to high school football games, don't go to high school football games. Explain why and do whatever. If you don't want to, you know, whatever. He's like, But you've not done anything else the way anybody else has done it, so why wouldn't you do this the Kaya Henderson way? And that was the most liberating thing that anybody has ever said to me. And I had to decide, okay, what is the Kaya Henderson way? What are the things that are most important to me? How do I communicate those to people? And then how do I do them? And that is how I want people to lead, with whatever their values are, authentically. And I think the world is hungry for authentic leadership and for more models of leadership. There is not just the, you know, X model or the Y model or the Z model. As many people as there are that are leading, there are that many leadership models, and I want people to find their thing and lead in that way. I love that, Kaya. This is one of my—you just made one of my dreams come true, because I've been trying to get you to sit down and tell me this story. Get you to sit down and tell me this story for a bunch of years, and I loved getting to learn from you. Thank you for making time for this. Thank you for having me. I appreciate it. Oh man, I hope this conversation made you realize why I admire Kaya Henderson so much. It's actually been a couple weeks since I talked to Kaya, and I just listened back through the conversation, and there are so many things in it that I've just been thinking about since we talked. One thing the conversation really left me thinking about was that it's one thing to be clear for yourself, to have a vision or to know what you want to do, and it's a totally different thing to create clarity for others and to bring people with you. Like so much of what you hear Kaya saying, and I think so much of what made her so effective and able to lead through this really complicated change was her communication. And she talks about it a lot, but like bringing people with her. And I think it really is so powerful what she said about like people just want to understand. They can handle complexity and they can handle, you know, that there are no good choices, but they want to understand why. And I think that's part of what she did in building that partnership with her community was bringing people along. And I think it was just, it's just such a cool, powerful example of doing something that is so, so hard. The other thing that I just loved is, you know, the thing she said at the end about the Kaya Henderson version of leadership. And I really think you can hear that as you listen to her. Like, she is such a unique and powerful leader, but part of that comes from her understanding, built over time, of who she is and who she isn't as a leader. I feel like one of the things that I really experienced in life, but for sure in work, is that you sort of early on in your career or early on in doing almost anything, you spend a lot of time trying to do things the right way. Like you're studying other people, you're studying other people trying to figure out what is right, what is good, like what does leadership with a capital L look like, or what does, you know, expertise in this area look like. And you sort of imitate others. You're like, oh, they do this, I should do this, and that's what leadership is, or that's what this great looks like in this industry. And in almost every case where I've done that, there's been this moment when I realized that there is no such thing as right, that it's all about finding your way. And you really hear it in Kaya's story about negotiating her contract with the unions, about, you know, just these very tangible examples of, like, things that other leaders wouldn't do or even notice, creating a circle of chairs instead of two tables facing each other, starting with stories about students instead of starting with conflict or, you know, negotiation tactics. That is the Kaya Henderson way. Like, she calls herself a lover, not a fighter, and you can just feel it, that authenticity and that realness in the way that she led. And I feel like the greatest form of all these things, of work in general, is what is the form that is authentic to you? What is your version of whatever it is that you're trying to do? Who are you? What matters to you? What is your version of leadership or life or work? Okay, I hope you enjoyed this as much as I did. I'll see you all next week. Work Life is a production of TED and Pushkin Industries. This episode was produced by Isaac Carter and Leah Rose. Banban Chang is our story editor. Mixing by Hansdale Shee. TED's executive producer is Daniela Ballarezo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Highlash, Valentina Bohanini, Lainey Lott, Tansika Sungmanivong, and Ashley Murphy. If you like the show and want more, come join the discussion on my Substack, Lessons. I'm Molly Graham. Thanks for listening. This episode is sponsored by Toyota. Independence is one of those words that sounds simple, but when you really think about it, it's deeply personal. For some people, it's about freedom. For others, it's about flexibility, or just having options that actually fit your life. That idea shows up in interesting ways in the tools we choose, especially now as more people think about switching to electric vehicles. Toyota's approach is to give people real choice. 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