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The Waymaker Approach: Leading with Purpose, Authenticity, and Curiosity

Education leaders discover that empathy and genuine curiosity transform how they navigate burnout and rebuild meaningful connections with their teams

This story was produced through MarketScale. See how Education Technology teams put it to work with Executive Thought Leadership.

By Kevin Dougherty · Education LeadersJustin RichardsonLeadershipWaymaker Leadership Development
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Key takeaways

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Education leaders discover that empathy and genuine curiosity transform how they navigate burnout and rebuild meaningful connections with their teams

Today's education leaders are under immense pressure, juggling administrative duties while trying to stay connected to their students, staff, and communities. Many are searching for ways to lead with greater authenticity and purpose. With teacher burnout and turnover reaching critical levels, there's an increasing need for leadership that prioritizes human connection and values-driven action. A waymaker can guide others with empathy and clarity, helping them navigate challenges and rediscover their sense of purpose. These individuals inspire and uplift those around them through their thoughtful, compassionate approach to leadership.

How can education leaders embrace this Waymaker mindset to create more meaningful connections within their schools? And how can they ensure their leadership remains authentic in an increasingly metric-driven environment?

On Just Thinking, Kevin Dougherty, Chief Strategy Officer at 806 Technologies, speaks with Justin Richardson, President of Waymaker Leadership Development, about how education leaders can adopt the Waymaker approach. They discuss the importance of staying connected to values, storytelling as a leadership tool, and the role of curiosity in fostering meaningful relationships.

Key Takeaways:

  • Waymakers Influence Others Through Care and Purpose: Justin Richardson defines "waymakers" as individuals who help others find or remember their purpose, offering support and care that instills confidence and growth. His company, Waymaker Leadership Development, aims to foster this approach in leadership.
  • Soulful Leadership and Authenticity: Justin emphasizes the importance of being genuinely present and authentic in leadership. He encourages a "soulful" approach, which focuses on meaningful, values-based leadership that prioritizes relationships and care for others. He encourages a "soulful" approach, which focuses on meaningful, values-based leadership that prioritizes relationships and care for others.
  • The Role of Curiosity in Leadership: Justin highlights curiosity as a critical component of leadership, encouraging leaders to ask better questions and genuinely engage with those around them, fostering deeper connections and trust. Curiosity as a critical component of leadership, encouraging leaders to ask better questions and genuinely engage with those around them, fostering deeper connections and trust.

Justin Richardson has over 26 years of experience in education, rising from classroom roles to Assistant Superintendent. As the Chief Learning Officer of Lead Forward, he helped nearly 900 school districts across Texas. Now, as President of Waymaker Leadership Development, Justin is focused on guiding leaders to adopt a values-based, soulful approach to leadership.

Video TranscriptExpand ↓

Hello. This is Kevin Doherty, your host for Just Thinking. I am the chief strategy officer for eight zero six Technologies. And today, I have a fast friend that I've made just in the past several months, and, I've enjoyed every conversation that I've had with this individual. And I I don't wanna say much about him because I want to give him the opportunity to introduce himself to you. So, Justin, would you tell us about who you are and a little bit about what you do? Kevin, thanks. And thanks for the opportunity to join you. Listen. You're right. Whenever you talk about becoming fast friends, you're one of my favorite people to just think with. So, so thanks for letting me be part of this. And, you know, it's nice to meet you. I am Justin Richardson. I've been in education for twenty six years now. From every role in a school district up through, right at assistant superintendent. Then I left the school district and I was the chief learning officer for a company called Lead Forward for eight years. And I had a chance to with Lead Forward. I think the last year we worked with almost nine hundred of the eleven hundred school districts in the state of Texas. So I have had a chance to work with the HISD that is Houston and the HISD that is Hereford. So, you know, both both of those. And, and I loved I loved the opportunity to get to go throughout the state and help people understand accountability, help people understand really good instructional practices and and build confidence through that. Lead forward work was fantastic. I loved it. And then, Kevin, I had a calling, that, you know, really, really weighed on me, for a while to look at how could I level up my support for school leaders, really just for people. But but starting out with school leaders, how could I do that? And so I decided to. And I I launched off from Lead Forward this past year and started a company called Waymaker Leadership Development. And, I am the president of Waymaker Leadership Development. We we all everyone that's hired has the same title actually, though. We're all soulful leaders is what we call ourselves. So, thanks. So that that's what we're doing now. And I'm just helping people, through that type of work. And I'd love to dig into it more, but that's what I do. I always have to tell people that, you know, I'm I live in Canyon, Texas, just south of Amarillo, Texas, up in the Texas Panhandle. So that's that's it. People say, we love your lake, Justin. And I have to remind them that, no, I'm in the Panhandle. That's that's Canyon Lake, Texas. So it has a beautiful lake down there, but, we're we're up in the Panhandle. We have a couple of trees, and do that. And so, that this is where family is, and and I'm just really honored to get a chance to support people, through the work that I do. I love that, Justin. So you, so you mentioned the name of your organization, Waymaker. So if you would, for our viewers and our listeners, define the term Waymaker for us. Oh, good. That's a good question. A good conversation. I you know, maybe I'll I'll start with this, Kevin, that think think about this. Have you had people in in your story who are those people who, when you interact with them, they they make you feel at ease or they make you feel more confident. They they help you believe in yourself. You know, you just I feel like I'm just a little better person after I spend some time with them. And, you know, I I think those type of people in in my life, I I consider them way makers. They have helped me find my way, maybe not even find my way, remember my way, remember the way, as I start working through my career and and life. And so to me, waymakers are people who help us stay focused on our purpose, remember our purpose. And that that's why we picked this name for the company. I love it. So you're, you clearly have had some influential waymakers in your life. So do you mind sharing who a couple of those waymakers were and and what made them waymakers for you? Of course. This one will be this will get me in trouble, Kevin, because I'll leave I'll start to leave someone out. So, if we get a chance to speak again, I'll go back to the to the Alright. That's a promise. You know, and I I jokingly say that, but there are so many of those people in my life. And, you know, professionally, I so here's a connection with eight zero six. Professionally, whenever I was a district administrator, in the office right next to me was a lady named Leslie Lauder. I know her. I I know her. Yes. I think at eight zero six, you guys know Leslie. And, Leslie's one of those people. And she was one of those people that I could go talk to and, you know, and share share, here's my problem I'm bringing you. And then she would ask questions that would get know just in what's but what's really the problem? You know, what are you really struggling with? And and she would give me time and talk to me and and be personal and human with me, to do this, but then also always bring me back to, are we doing the right thing for people? And Leslie was one of those way makers for me, Kevin, professionally. And and, there's so many, that I I love dearly. And I'm not gonna start naming names because I'll I will leave someone out. But personally, you know, I I think of way makers in my family. My my mom, my dad are way makers, in in their own ways. You know, my mom, was always a person who did not have professionally. She doesn't have a resume that is that is interesting or impressive to people, but she was my mom. You know? And and her love and guidance and focus made her a way maker for me. And my dad, I'll I'll talk about him for a second. He he does have that resume that's impressive. And, you know, and he, he he I think forty four years of law enforcement when he retired. So at at some point, someone had to say, do you understand how this works? You can you can stay home, you know, if you want to at some point. And, but he he love, love that work. And, you know, for a while, Kevin, he was one of the most, probably the most decorated and well respected law enforcement officers in the state of Texas. He he was sheriff of Randall County for twenty plus years. And I'll tell you, Kevin, it's really interesting for him to growing up. And and then as a young professional, he would share sometimes, some things that he was doing or, you know, how he address. And I would go, yeah. Yeah. Yeah. Sounds good, dad. But, you know, I'm I'm I'm sophisticated and fancy and, you know, and and I and so I I didn't always listen the way I probably should have, during those times. But I started, I started paying more attention as I grew older. And, Kevin, one of the things I've I've noticed that the this Randall County Sheriff's Office was often recognized as one of the best places to work in our area. That people loved it. They came. They they wanted to go work there, and they stayed there whenever they did. And so I was talking to my dad right about the time he retired. And then I started thinking about this, this idea of way maker. I said, talk to me again. Tell me, why do people love working for you and why did they stay? Because we're having some issues in education with people staying. And I'd I'd like to learn a little more now. And so he would go back through and tell me some of the stories that I know I had heard before, but I never made the connection. You know what I mean? And and one of the stories, he he said, you know, Justin, here's here's an example. He said, everyone that we hired at the Randall County Sheriff's Office, I I always got a chance to talk have have conversations with them, whether it be in small group of hires or one on one or and he said, you know, I told him this story. And he he said, this is this is the story I told each person about our sheriff's department and our expectations of this. He called it the lawnmower story. Mhmm. So, Kevin, if it's okay, can I share the lawnmower story with you? I love I would love to hear the story. Oh, yes. That that's that's an anticipatory set in the classroom. So we'll go with the lawnmower story. It's Tina now. Let's go. Good. So the lawnmower story is this. He said, I I want you to picture this. There's a lady, in the rural part of the county. She's in the kitchen doing dishes, looking out the kitchen window, and she sees her neighbor mowing the yard. And at some point, the neighbor collapses and appears to be unresponsive, and she's calls nine one one. He my dad said, at some point, you may get that call working for the sheriff's office. And if you get that call, here are my expectations. He said, I want you to be the first one on the scene. Beat the ambulance out there. And when you get to the scene, I want you to go out and assess the man. If he needs to, that take take your defibrillator out of the trunk, hook him up. If he needs to be shocked, apply the shock to that. If not, do CPR until the ambulance gets there. And when the ambulance gets there, I want you to help transfer services. Let them know what's going on, what you've done. Help them get the man secure, stable, loaded up, whatever needs to be done there. And while they're wrapping that up, I want you to go into the man's house, and I want you to make sure there's nothing on the stove, that there's nothing in the oven. Grab his keys and lock up. Then I want you to escort the ambulance to the hospital. Make sure they make it there safe. When you get to the hospital, I want you to get out, help them get the man transferred into the emergency room, make sure someone there has his keys and they know what was happening with that. And my dad would tell people that that's where that's where the story ends for many sheriff's departments. But he said in this sheriff's department, the next thing I want you to do is jump back into your car, go back to the man's house, and I want you to finish mowing his yard. And, Kevin, that he he would tell them that's what we do. That's how we serve in in this county. That's what that's our job. And if any of that that I described to you isn't something that you're willing to do or that you see eye to eye with, this is probably not the place you wanna work. And what what I love about that I mean, I sharing your values with people through storytelling, those kind of things, having that kind of expectation, that's a way maker. When you said define that, that's a way maker. That that's helping people understand that it's about caring for others. It it's it's not about that's not my job or, you know, I I we don't do that part. It's our job to love and care for people. And and when you have leaders like people who think like that, that's it. And one of the things I share with leaders all the time is that this is about values too. I mean, he could when when you think about that story, you hear, I want you to be responsive and well trained and collaborative and service oriented? You know, you you hear those values come out in that story, but it's it's different. Just putting those words on your letterhead or painting them on the wall is one thing. But but bringing those values to life through a story of how we do our job, that's that's good. I I can think of a very good teacher in history that told stories. I can too. I can too. And I tell you what, that, it's not only a beautiful and a powerful story, but it's not just a story is my guess. He's your father. But my guess is that story is a reflection of the way he does and did everything himself. So he went back and mowed that lawn. That's what he would do. And and that that message of going beyond the minimum expectations, exceeding those expectations, doing whatever it takes to serve others, in a way that ultimately, you know, we would greatly appreciate having been served ourselves. So are there other waymakers out there? Because you you've been traveling. I see you on social media, and I love everything that you're putting out there. I I don't just love the fact that you're posting. I love the smiles on the faces of yourself and the other people. And I don't know most of these people. I know some of them. But I don't know most of the people with whom you're visiting. But what I see in their faces is joy. I see it in your face. I see it in their faces, and that makes me feel good. I get a warm fuzzy when I see your posts. So I know you're meeting other way makers. Is there something you'd like to add to that? Yeah. They're all over, Kevin. So one, you mentioned social media. I'm gonna give a plug. Any of the social medias look for BA way maker. Just search for that. Kinda hunt for my face around there. You'll see us. So so come and do that. But, you know, Kevin, when we started our social media plan for this business, it was like, do we wanna do it or not? And we said, let's get in and try it. Let's see what happens. And, here's our metric for whether social media is working or not. Are we having fun? That's it. I I I don't care about the number of likes or number of followers or number. Are are we showing our love for other people? Are we having fun with this? We do it. So to hear you respond to that, that way it means that we're doing we're doing what we aim to do, with this. And it's just to bring a little a little joy into the world and especially in the world of education. So so come follow us. It's kind of fun and, and I hope it does the same thing for you that it did for Kevin. But, Kevin, I, you know, I talked about Leslie, I talked about my dad, I shared those stories. So can I throw, can I throw it back at you? So what, So so if you understand the idea of way maker that I was sharing, who is a way maker in your life? Describe that person. Wow. That is a great great question, and I I love you flipping the script here, brother. And as I think about it, my sense has always been that I have more to learn from other people than they have to learn from me. So I have thousands of way makers in my life because, you know, I I approach interactions, I approach relationships with that mindset. So because of that, I I just have, again, hundreds, if not thousands, of people that have been way makers for me. You know, I love your, mention of your parents and, specifically, your mom not having the the resume, the formal resume. I had a mom like that. She raised six kids. You know, her whole focus in life was taking care of us and, and raising us well and so forth. And so certainly a lot of way making there. And then, a a grandmother, my dad's mom, who is a woman of deep faith. And, she left reminders for me or said things for me along the way that have resonated years, beyond her passing and her time here on Earth. So I've had that. But I think the, the way makers for me more are I'm so interested in younger people. As a teacher, I learned from my students. I taught third through sixth grade. I was an elementary principal. And I just saw the students as people, little people that I didn't see them as children necessarily or that, you know, their ideas were of less importance because they hadn't had as much experience or knowledge or wisdom yet. I I was always interested in that, in our own children who are grown now, and that in in the workplace, working with people younger. I'm in my sixties now, so working with folks in their twenties and thirties. These folks are are, are way makers for me. And, you know, I went through an incredible, dramatic health incident almost five years ago, and, and the role that my wife had to play through all of that. In fact, Waymaker was a song that I shared with you before that that helped them through my eighteen days of being in a coma, you know, on the on the brink of of death each day. So, so it's really powerful. So lots of way makers for me. So thank you for asking the question. I don't know if I fully answered it for you, though. You did, Kevin. And I think that's the that's the thing is that they're all over the place. We just I as a matter of fact, there's probably more who are than aren't. But but sometimes when we get busy in life and things are overwhelming and we we kinda lose track of or sight of our purpose, we forget that we are that person for others. And, you know, and I think one of the gifts that I've been given this past year, and and I say this sincerely, Kevin, is some some conversations with you. You know, there's been a couple of times I've called you on the phone driving down the road somewhere and just said, hey, Kevin. Can I just can I just share an idea with you? And and I don't ask you to do this, but what I'm really saying is, would you just be excited for me and believe me? And that's that's I I call you because you are a way maker. Right, Kevin? And that's the, you know, I I think that's the gift that we have an opportunity to give those people in our lives when we slow down long enough to just listen, care, be sincere about things. And, you know, the world of right now in education, that's where I'm starting, this idea of leadership development. In the world of education, we there there is a culture of busyness that we kind of celebrate. Right? And and it's real. There's a lot of real busy work to do. There there's no doubt. But it's those people just reminding leaders that it's important to hit the pause button and be present with people. That that's how you keep good folks around, and and we need a lot of that right now in in the world of education especially. So We do. You know, a recent guest on the Just Thinking podcast was Yuri Calderon, and he's the executive director of the Small School District Association of California. And so he works with all these school districts. Sixty five percent of the school districts in California, they have over twelve hundred, are deemed small school districts, meaning they have I forget how the number is, less than a couple thousand or something. And so he said that, that's where they're struggling because there's so many expectations in terms of reporting and that kind of thing that's been, mandated legally for them to do. They said that they have a choice. They could sit behind a computer screen hours on end, trying to meet these deadlines and complete these reports, or they could be out there with students and teachers and the community and being present, as you said. And, of course, Yuri wants to, advocate for and to lobby for these administrators to be able to have that time to be present because he knows the power. He's seen it firsthand, the power of that presence. So, what is it that you and your team are doing to help develop that, way maker, approach to leadership? Yeah. That good question. And I and I love the focus on being more present for people. You know, when especially in those smaller school districts. When when you're the superintendent who may be called on to be superintendent and bus driver and cook chicken nuggets, today, it it can be overwhelming and and you sometimes forget, not not forget. Just lose sight of, that grander purpose that you're there for. So one of the things we're doing, I have an incredible team of Waymaker. So, go go find our team. We if you go to b a waymaker dot com, you'll you'll find our group and and read a little bit about our team. They're amazing people. And what we're trying to do, what we're dedicated to doing is just any type of support we're giving. We're trying to find a more soulful approach to that support, a more more soulful solutions to this and really help people understand the importance of pause and defining that in your life. What does pause look like? Because, Kevin, when we pause, we remember our purpose. Those those, the important stuff gets loud whenever we slow down and get quiet. And, you know, and we we don't do that enough. So how do we we help from a leadership perspective, build in pause, but then also look at a very, ethics and values based leadership, and also looking at the idea of relationships and how to be more authentic in this. I I think people now are craving authenticity when when especially in this world of AI. When when we can get everything done there, the the beauty right now is when you find someone who's willing to be authentic with you. And and you see it. It's standing out more and more. And I think people are wanting that. So we're really trying to find these soulful solutions for people and just reminding them that it's not it's not just what you do, but it's who you are as you're doing it that makes the biggest difference. And, so we build that into this and it starts with hiring great people. So I've got great people, that do this and then also looking at how to support people, in in those things. The other word, if I had to put one word into what we do whenever we're creating social solutions to this. And it it's gonna sound but it interesting, but it's the word doable. And, you know, one of the reasons people are leaving this profession of education at a record rate is that they what they'll what they say in exit interviews is that I was given a job that wasn't doable. And so one of the things I really challenge my team with is we we came up with this really cool thing. We're all smart people. We did we can think big. We've read all the books that are back here. We we can create complicated stuff all day long. But can we create solutions that are really doable for people? So in the time that they have, with the skills that they have, with the staff that they have, is this solution really doable for you? And then, you know, and and then also in a way that allows you to not be stuck behind the computer for hours and hours a day that allows you to be present with people and lead it. And so those are the things, Kevin. We've we've put together some support for leaders. We've put together support for teachers and looking at foundational practices in the classroom. One of the things I've noticed is that we we got really fancy and sophisticated with a whole lot of stuff. But now we're turning over teachers at this rate that we can't continue to be fancy and sophisticated with. So we've got to go back to some foundational practices in all classrooms that that are in place and secure. So foundations, we're looking at teacher leadership. So one of the things, Kevin, that we do is, Kevin, you've been a third grade teacher for three years now. The kids love you. The parents love you. You're now in charge of the third grade team or you're now the campus instructional coach or you're and one of the things we're noticing is that people are not prepared to go there. They were great with leading kids. That's awesome. Leading adults, sometimes that's very different skill. Or we're helping people think through that. What would that look like? And then, of course, all the all the work that we're doing with leaders to create a more soulful approach to leadership. You know, you shared a lot of this at a recent eight zero six learning summit that we had in June. And so I know you do a lot of public speaking, and you're very good at what you do. And if people are following me on LinkedIn, you've seen the posts that I put out there, and you will be following the Waymaker as well. So you'll get to see Justin there. But, Justin, I just like to hear what that experience was like for you. You know, you've managed and coordinated conferences for years, and, so this is one in which you were a featured keynote speaker and did a breakout. What what was it like for you to be part of that experience? That that was awesome. You know, and, Kevin, I talked about two words. I'll I'll share I'll make the connection back to eight zero six in the conference that we had. One, I talked about the importance of authenticity. And and here's what here's what you get from the team at eight zero six. And the conference you guys put on was just authentic relationships. Well, you know, it it felt real. It it felt personal. There I I had some I have some great friends from that opportunity. So we we had a good time. We were well cared cared for. But I if I had to describe it in in one word, it it is authentic. And then, you know, I think the other one I I might tie back to this. And I from my early days of working with Leslie, whenever she was working together with me on campus improvement planning, things like that in the district, all the way through to the resources you guys have now, I talked to you about that word doable. And and I think that's the other thing that eight zero six, like Waymaker, is committed to creating doable solutions for the people that are having to do the work. And, you know, so I'd I'd love that. I I love the fact that people were there, and they felt were well cared for. And they felt like they were getting some some solutions that were doable with the resources that they they have. So That's awesome. It was greatly rewarding feedback. So I appreciate that. Yeah. Of course. So we're we're coming to the end of our thirty minutes, and you and I talked about that before. There's, you know, some thoughts out there about podcast. Keep it to twenty to thirty minutes, so forth. Maybe a drive to work, a drive home, or whatever. You have a little bit of time to listen. This will be available on, Apple Podcasts as well as Spotify. So I hope people will will listen if they don't have the time to sit and look at our, handsome faces here on the screen. So, but I like to wrap things up with giving you the opportunity to have the last word. So, Justin, is there anything else today about what you're just thinking that I did not give you the opportunity to speak to during the course of this episode. Kevin, I I have a lot of thoughts that I'm just thinking, you know, and and good people like you bring out more of those. So, you know, Kevin, I I think one one of the posts that we were just working on recently was about the concept of curiosity. And so I I have been just thinking, about how important it is to be genuinely curious about people. You you've seen those leaders who, will you'll tell a story, but you can tell their eyes are somewhere else. Their head is somewhere else. They're not with you. They're kinda giving you the nod. Yeah. Yeah. Let me know. And, and then when you sit down with someone who's really interested in you, who's who's really there, that is a gift. So I I've really been thinking about this idea of the role of curiosity, authentic curiosity in leadership. How do we ask better questions? Do you ask great questions? I think the the art of asking a really good question for leaders, is something I'd like to keep playing with. And and helping people understand how important it is to be genuinely curious about people, around you. And and when you are, it it just it opens up a whole new level of engagement from folks that are around. So I I wanna keep playing with that idea. And what does what does that look like in in leadership? Well, and on that note, I I love that note. You know, you're mentioning eight zero six. Be curious is one of our core values. So, but I I like it especially applied to people. Be curious about others. It's so in keeping with everything we've been discussing over the past thirty minutes. Before we wrap up and say goodbye, I know I said that was the, the last word, but don't you have a book? Oh, I have a book that's coming. So you guys will be watching for it. So it'll it will drop soon. It's about soulful leadership. And, maybe Kevin, there's a chance for us to reconnect whenever that does drop. I'd love to share, more of that with you. So thanks, Kevin, for that. Hopefully, it'll be out we'll be out and be ready to go soon. Well, let's do it. Let's make a plan. Let's follow-up part two of this conversation when the book is out, and we can share more with folks about that. But thank you for your encouragement to be curious and telling us about what a way maker is and encouraging all of us really through that to be way makers ourselves. It's been a total pleasure, Justin. Thanks for being part of Just Thank You.

About the author

KD
Kevin DoughertyChief Strategy Officer

Kevin Dougherty is the Chief Strategy Officer for 806 Technologies. He has spent the past 39 years as an educator and serving educators. A graduate of the University of Massachusetts/Amherst, Kevin earned a Bachelor’s Degree in Multicultural Education. He later earned a Master of Education Degree in Education Administration from the University of Massachusetts/Lowell. Kevin was a classroom teacher for ten years in the Dallas, Boston, and Houston areas. He then served as an assistant principal/principal of Title I/Bilingual campuses in Fort Bend ISD and Irving ISD. For the past 22 years, Kevin has been serving educators throughout Texas and the nation in various roles supporting sales/marketing, professional learning, and overall company strategy. He has been married to his wife, Michelle, for 33 years. They have two grown children who both live in the DFW area.

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KD
Kevin Dougherty