Igniting Insights with Barry Binder: July 2026

Speakers: Barry Binder • Lindsay Keller • Jenny Breeding

Barry: All right, today I’m pleased to be joined by Lindsay Keller and Jenny Breeding, who are both gracious enough and willing enough to spend some time with me, have a conversation with me. Thank you both for joining me. Appreciate it. We were having this conversation in my living room and my wife decided to get a puppy a week ago. And so we’re hoping that there’s no puppy noises, but if there are, that’s just going to happen. So before we get started, I think it’s a good idea for me to explain why I’ve asked you both specifically to join me. And to be clear, for everybody that’s listening, we’re friends. We have no working relationship. I was introduced to both of you through my wife, Tracy, who worked with both of you in some capacity. Over the years and through getting to know each of you and the conversations we’ve had, I think, I mean, I probably have never said this to you, but you’ve both been very influential in transforming the way that I look at things professionally and personally. So probably most impactful in helping me sync up the way that I live my personal and professional life. So I’m just kind of a true me 24-7. So I find you guys inspirational in that way. So that’s why I asked you to talk to me today. So you both just always have such unique and thoughtful, thought-provoking takes on things. And so I always walk away from those conversations thinking more about something. And so I’m asking you to have that conversation today to share some of your thoughts with other people. Cool. All right.

Jenny: Thanks, Barry.

Barry: Sure. Well, so to start, would you mind introducing yourselves, what your title is, what your role looks like day-to-day, how long you’ve been in your current field, and then a little about the path that brought you to where you’re today.

Jenny: All right, I will start. I am Jenny Breeding. I am currently serving as the assistant principal at Chapita Elementary in School District 11, Colorado Springs. I think I am starting my 24th year as an educator. I started my teaching career as a fourth grade teacher Moved in to a role as an IB coordinator for the International Baccalaureate Program. This was all at the same school. And then from that role, moved into an assistant principal role, all at the same school. Moved from that school to another school, became a principal. Moved from that school to another school, was a assistant principal to middle school, and that led me to Chiquita. So I actually went to school to become a dietitian.

Barry: So I did not- I didn’t know that.

Jenny: Initially go to school to become a teacher. I wanted to work in a hospital as a dietitian. But I took an organic chemistry class and did not like that. I think it was my senior year, I called my dad and said, I don’t want to do this anymore. And he said, too bad, you’re finishing your degree. So I have a bachelor’s of science in food science and human nutrition. And so I have that bachelor’s and I moved home to the springs. I got that from CSU in Fort Collins, moved to the springs. And I think it took me probably I don’t know. I really am unclear on how all this happened, but probably three or four months to decide to go back to get my teaching like certificate. And I think that was like a year long process because I already had my bachelor’s. And I didn’t feel like super, like called to teach. Like I wasn’t like, I really want to do this. But I do remember like my mom was a teacher and my dad was a veterinarian. And he was like, always so like, proud of my mom. And he was always just like, gosh.

Barry: Your mom was a teacher?

Jenny: My mom was a teacher. She was an elementary school teacher. And my dad was always like, “gosh, kids, look at your mom. Isn’t that a great career? Like, look at her summer, her summers are off.” Like he always just was like, like talked so fondly of her career. So yeah, I got my teaching license and the rest is history. I’m Lindsay’s little sister, so.

Barry: Yeah, I was waiting to see if that would come out or not. Yeah, so sisters. So if you have the same story about your mom and dad.

Jenny: Yeah, yeah. So here’s Lindsay.

Lindsay: Yeah, she, yeah, well, we’ll see. Yeah, I was gonna give the disclaimer ’cause I couldn’t remember. Barry’s comments were so sweet in the beginning. I was sort of skipping over if somebody mentioned that we were siblings. So, but that was nice, the mention of dad’s admiration of mom’s career ’cause I wasn’t thinking about that, but it is true. It was probably more meaningful even than I would imagine it was. My name is Lindsay Keller. I’m currently serving as the principal of Achieve Online and Blended High School in Colorado Springs School District 11. This is my 23rd year in education and my sixth year in school administration. Yeah, I, let’s see, long story short, I Graduated with a bachelor’s degree in English language and literature, which we all know is super applicable in the real world, but was pretty sick of school at the time. And so I got my bachelor’s and kind of wanted to give myself some time to think about what I wanted to do moving forward. And as I was doing that, got a postcard in the mail advertising AmeriCorps. So I actually became a VISTA, yeah. the year right after college, sort of for lack of anything else to do. But I had two options. One was to do kind of disaster relief help as an AmeriCorps, as a Vista, or to be somehow in the field of education. And to Jenny’s point, had always kind of tossed around the idea of teaching. As an English major, you know, most of us do think about it at one point or another. And I agree, like watching mom and all of her friends and a lot of our parents’ friends were also educators and they were just happy, kind of fulfilled, purposeful people. And so that was kind of a model for us. So I ended up in Alexandria, Virginia, working in a low socioeconomic community opening a computer lab for some kids who didn’t have access to technology at the time, which is a story for another day. Came home from that. And our high school principal was currently acting as principal at Palmer High School, which is another school here in town. And she called me out of the blue one day and said, I need an English teacher. And I said, I don’t have my teaching credentials. I’m just sort of trying to figure out what comes next. And she said, well, I’ve been to HR and I’ve seen what’s there and you’ll do a better job than anybody else. So what are you doing on Monday? And this was like a Thursday. And I said, well, I don’t know, Jackie, like you want me to come be a teacher on Monday? And she’s like, yeah, kind of. So that’s how I started teaching. I came and met with the department chair the next day and I’m sure he was like, what in holy hell is happening right now? Like, I’m going to put this 23-year-old in front of students. And that’s exactly what they did. So I spent a year kind of as an emergency substitute, for lack of a better word. And that’s how I got into teaching. Luckily, I liked it. And so I spent the first 12 years of my career as a secondary English language arts and English teacher at the middle school and high school level. And then I spent a year as an instructional coach, and the role of an instructional coach in a school is really just to help teachers become better teachers. But a lot of that involves classroom observations. And it was kind of a light bulb moment for me about the vast difference in the experiences that kids were having. Some were having spectacular experiences, but for a lot of kids, it’s really a pretty terrible situation. And, and it has a lot to do with who your teacher is, as we’ve all kind of experienced. So that kind of changed things for me and shifted me into kind of a different path. So after that, I actually stepped away from education for a minute because I was pretty disheartened by it and needed some time. So I did that, but really missed it and stumbled across a pilot program for an online school, which never really interested me because relationships with kids is really important. And I didn’t want to have that distance, but this was a person who was going to do it a little differently and have kids in person, but accessing the flexibility of online learning. And so I helped open that school in 2014 and 2015. I don’t know, it all runs together. Anyway, Spent 10 years there as a teacher and then a teacher on special assignment, the assistant principal, and then the principal. And moved from that school two years ago back to District 11, which is where I live. I live inside of District 11. We graduated from District 11 schools and just sort of felt like at the end of my career, I wanted to come home and finish things out kind of from where we were from. And I’m happy to be here.

Barry: So you both backed into career and education, kind of, right?

Lindsay: We did. Yeah, we did.

Barry: Yeah, you’d never know. I’d never, I guess I never knew that both of you had different backgrounds. I just assumed, I didn’t know that your mom was a teacher either. So you both started off having really no, necessarily no intention into going into teaching. But then, I mean, as a liberal arts major as well, I always said, no one’s coming around knocking on the door looking for a guy with a bachelor’s degree in Russian history. That just doesn’t happen. So you’re like, well, maybe I’ll teach, or do something like that. But so you had influence from your mom because you watched her in education and then it became a choice for you when you decided organic chemistry wasn’t a path that you wanted to follow. Yeah, interesting. So in my world, I know we’ve talked about this before, my focus is centered on client experience. And I view my clients as my lending institution, client partners, those are my external clients. And then my colleagues, I always look at it as my internal clients. So my primary focus is ensuring that the experience of both those clients that are being served well. So as I was preparing to talk to you both, I was thinking about this conversation and I started to wonder who your clients are, right? In your world, I mean, who is the client? Is it the student? Is it the parent? Is it the community? Is it your colleagues? Is it a little bit of all of them? My client sets are pretty well defined and I started thinking about your world and I couldn’t really put my finger on who your clients are. And so how you best determine what a good client experience is. And maybe it doesn’t even fit for the world of education. I think it does. Maybe the terms are different. But yeah, so what, I mean, who’s your client? As either an administrator or as a teacher, who’s the client?

Lindsay: I’ll take this one first. I actually, can I take this one first?

Jenny: Who’s going to have the right answer?

Lindsay: I will. No, I’m just kidding. I actually, this is an interesting question that you posed to us ahead of time. When we opened Village High School, which is the school I mentioned that I helped to start, we talked a lot about end user. So we didn’t use the term client, we used the term end user. And how one of the mistakes we had made in high school education a while back is that we lost track of who the end user is, and that’s really the student. Now, I think in my career that the answer to that question has changed. So when I was a teacher in the International Baccalaureate program, super high achieving kids, super involved parents, I maybe would have said parents were more of the folks that I was most concerned. I don’t know if that’s right or wrong, but at the time, that’s sort of how I felt about it. As I think about it now, though, I sort of feel this obligation to the world around us. I mean, everybody goes to school or some form of school, and we have this obligation and this responsibility to help young people enter into the world and hopefully try to make it a better place in some way or another. Economically, sure, socially and responsibly, I hope so. Politically, maybe. So it’s interesting as the course of my career has unfolded, how the answer to that has changed. But I think in my heart of hearts and in my gut, it will always be about kids. The kids? Yeah, I mean, and especially now when I, it’s not that I care a little less, but I feel a little bit more confident in my skills. I’m a little bit more willing to say, yeah, but what you want me to do isn’t good for the young person that I’m working with. And so that’s gonna be my primary focus and the central kind of, when it really comes down to having to make a client-based decision, I’m gonna make the decision that’s best for the student. The student first. Yeah. Yeah, I mean, I agree. I think…

Jenny: So schools will always, like, the right answer is that your client is the student. I would say most schools will say that your client is the student. And I mean, schools exist to improve like conditions for kids. But I would say like as an assistant principal, like my main job is to make the principals job easier. So she’s my client. She’s one of my clients. Obviously, our community is a huge client base, our school community. But like most of my work is centered on students, but it’s through empowering teachers. So I feel like a lot of my work is an assistant principal. And that’s why I love my job as an assistant principal, because I’m not dealing with a lot of the stuff that principals have to deal with, like above them, like the central office stuff and the stuff outside of schools. I feel like a lot of my client base is teachers, because if you’re improving conditions for teachers, that helps kids. So I feel like there’s just a lot of clients that we’re working with as administrators. But yes, endgame is for the community, like whether that’s local or, you know, beyond. Broader. Yeah, broader community, for sure.

Barry: You both would agree to some extent that your clients are varied, multiple clients. So, what is, I mean, in your setting, what does a great client experience look like? Is that possible to define what a great client experience looks like? I mean, holistically, obviously… that experience would look different for the student or for teachers or for, in Jenny’s case, her principal, right? Or for the community at large. But so what is, I know it’s a nebulous question, but what does a great client experience look like in a school setting? I mean, yeah, it’s different for everyone. I mean, everyone comes to a school or any place with different life experiences and different perspectives. So.

Lindsay: A great client experience means different things for people. Different people. Yeah. Yeah. Yeah, I think the trickiness and the layered part of what’s layered about schools and why we hear in every presidential election, right, presidential candidates say, I’m going to be the education president. And none of them have ever been able to figure it out. And part of it is because Unlike, it isn’t cut and dry, unlike in a business. So as a small business owner, as in the other part of my life, it’s really clear, like, we love the work we do. We love being an integral part of the community, but we’re there to make money. And that’s the primary focus. You know, it depends, for a school board, the end result needs to be about test scores and about metrics, and that’s probably true for a superintendent as well. For parents, parents want their kids to be happy and to find a path in their life. And for kids, they want to feel seen, and they want to feel valued, and they do want to learn something. I mean, kids are curious creatures. And as a system, because there are so many perspectives, competing perspectives, we tend to beat that out of them a little bit. There’s nothing like a school experience to kill curiosity in a kid. And that was a terrible thing to say as an educator. Yeah. But one of the things I’m currently doing is thinking about my opening activities with my staff. And I want to open by talking about what were the things you loved about school and what were the things that made school a struggle? And how can we capitalize on the things that we all agree we loved about it and minimize the things that made it hard? It’s hard. There are a lot of fingers in the pot.

Barry: So you have to pivot constantly based on who your client is. So you have to be able to pivot and to be able to focus and shift your attention and shift the way that you’re serving that client for whatever their expectations are, or your expectations constantly. Yeah. Interesting. Yep. Okay. So I never thought about that. So, one of the topics I think that we’ve discussed, again, informally for sure, is centers around leadership and leadership styles. And some people, I think, are quote/unquote “natural leaders” and some people have to work really, really hard at being a leader, I think. And their leadership skills. I mean, personally, I don’t think that I became comfortable with being a leader or really understanding or finding my own style as a leader until I felt really comfortable in my own skin. And I think that takes like maturity, right? And either way, I mean, whether it comes naturally or not to people, I don’t think it’s possible to be a really good leader unless you have a high level of self-awareness and some intentionality around it, right? So I always hate that, like “I’m a natural leader,” I’m like, are you really? I mean, I think people are drawn. Some people have like innate leadership skills, but being a good leader, I think takes work and intentionality. It evolves over time. You have to navigate things that are happening all the time to be a good leader. At least that’s how I see it. So From your perspective, I mean, when did you first realize that you were a leader and not just somebody doing a job? In a classroom, maybe it’s different because you’re a leader maybe from day one, right? Because you’re actually leading a classroom. But I don’t know, do you look at it that way or when did you recognize yourself as being in a leadership role?

Lindsay: I’ll pass this to you quickly. I don’t know that I recognized myself as a leader. It was about other people saying, you have potential as a leader or you are a leader. That same principal I talked about before, I was a young teacher in her school and I overheard her saying to one of her assistant principals, Lindsay has talent and she’s a truth teller and she’s going to be a leader for us. And it was like, Okay, I guess I could see myself in that way. And so for me, it’s been as much about other people seeing that potential in me as me sort of seeing it for myself. I mean, let’s be honest, leadership is pretty vulnerable. It can be a really crappy place to be. You’re the person who’s out there for everybody to criticize and When they like you, they love you, and when you’re doing it wrong, man, there’s no bigger target on your back. And so I will just say, I was happy to be a quiet and reluctant leader until there were others in my life saying, nah. I think you actually kind of have more to offer and maybe more of a responsibility than that.

Barry: So you weren’t vocal about your desire to be a leader. There’s a term, like a phrase, actually one of my colleagues said to me, it’s like, “Quiet mouths don’t get fed,” right? If you’re not expressing your desires or the things that you want, then people around you won’t necessarily understand that it’s something that you’re looking for unless you’re vocal about it. So you never found yourself in a position being vocal about wanting to be a leader or expressing a desire to be in a leadership role?

Lindsay: Not for a long time. I mean, remember, like I was in traditional high school and I was looking at assistant principals. And they were carrying walkie-talkies around and busting kids for wearing hats or being on their phones or getting yelled at by a parent. And I’m thinking, I don’t want anything to do with that. And it wasn’t until I found a different environment where I could imagine leading in a different way. But that’s gotten me in some trouble. I don’t lead like a typical… administrator does all of the time. And that can be really hard. And it’s resulted in some difficult moments in my career, but I wasn’t going to do it any other way. But I had people talking to me about leadership early, early in my career. But again, I was looking around like, no, I think I’m good. I wasn’t curious enough to understand that some– Well, a lot of what you can’t see is the fun stuff, the visioning and the pulling people together and what Jenny talked about with empowerment of people. That’s the quiet part of leadership. And that’s the fun part that you’re not always witness to just out in the world. That’s the stuff that gets really fun.

Barry: Yeah.

Jenny: Yeah, and same. I mean, my first leadership role was my principal, who I admired, I mean, she just tapped me on the shoulder and asked me to step into a leadership role. And my first administrative role was my area superintendent needing me to step into the assistant principal’s role because our principal had to leave and there was a space open. So, and that was after me saying that I never wanted to be in school administration. So yeah, same thing. I don’t really remember, like, a time, like, an exact time. I just– I know that early on, people came to me for advice. And I think it’s because of my ability to, like, simplify things. Because teachers are notorious. Educators are notorious for overcomplicating things. There’s so much noise. And the educational space, we do it to ourselves. There’s just so many initiatives and so many stupid things that we’re doing. We just are just overcomplicating so many things. I would go to trainings and go straight back to my classroom and implement whatever we learned. And my teammate would come in and she’d be like, oh my gosh. you’re crazy, but I would be able just to simplify it and make it easy. So I think people were drawn to that. I vividly remember one of my colleagues coming in and just being so frustrated and saying to me, you just make everything seem so easy. And I’m like, oh, sorry. Sorry, I mean, so I think that just people were kind of drawn to me early and I guess that made me feel like a leader.

Barry: So people maybe realized you were leaders before you realize you were leaders yourselves.

Jenny: Yeah, I think so.

Barry: They recognized something in each of you before you like consciously said to yourself, that, “Hey, I’m in this leadership position” or “I’m going to take this leadership role.” Yeah, that probably happens a lot, I guess, right?

Jenny: And it definitely makes me want to do that for other people.

Barry: Yeah, for sure.

Jenny: Because I don’t think people see that. I definitely don’t see people like step up to the plate very often.

Barry: Yeah.

Jenny: Or see it in themselves.

Barry: And maybe the people that do are maybe the wrong people to be in those positions too, right?

Jenny: A lot of the time.

Barry: Yeah. Interesting. So what’s something that you’re still learning as a leader?

Jenny: I think one of the things that’s really hard for me right now is learning how to show empathy to people who are constantly complaining or finding cracks in the system. I mean, that is just hard for me. And that’s personally and professionally.

Lindsay: Yeah, gosh, there are so many things which I think should I mean, I hope that means that I’m always wanting to grow in my leadership. But for me, it continues, I think, to be about kind of similar to Jenny, like patience, understanding that it’s interesting. She talked about how we overcomplicate things in education. And I sort of think one of the reasons we do that is because At the center of our work are kids, and kids are complicated. I mean, in some ways, they’re very straightforward, but there’s just so much that comes along with them that can be very complicated that I think sometimes we fall into this trap of everything else must be really complicated because our work with them is. And so, yeah, just really continuing to make the important thing the important thing. And Yeah, I don’t know. I continue to try to work on being more of a listener and less of a talker, which can sometimes be an issue with me.

Barry: I mean, that’s becoming self-aware and having maturity too, right? In that role where you feel more confident, I think young leaders probably, I was certainly guilty of it. Somebody in a leadership position, I felt like I had to be more in front of the room and be someone that was taking charge and saying more because I was in this position of leadership, right? And that’s, I think that’s probably natural for people, but it takes some self-awareness and some years and some maturity before you realize you can just kind of lay back and let the game come to you a little bit. And it’s better because you let people work things out. And that’s just a different way of being a leader. Instead of being like a forceful leader, you’re being more of a passive leader. I think probably people, I don’t know this for sure, but I Anytime I’ve recognized that happening, I feel people take to it better than they would to somebody that’s like trying to rah-rah too much or trying to give them way too much direction in coaching. It’s like just more of a passive kind of way of doing it, right?

Lindsay: Yeah, that’s a good way of saying… You’re saying what I was trying to say much better, Barry. Thank you. But yeah, you don’t have to have all the answers. You just have to be the person who’s going to help to pull it together and make the nuts and bolts of it kind of work for everyone in the end. But you don’t have to be the brainchild of everything. And in fact, you shouldn’t be.

Barry: Yeah. I mean, I think that’s over-managing, right? And I think a lot of times, I mean, I tell people this all the time. I constantly, I will remind people that I’m an overt thinker. Like, if I sit down and start talking, don’t think like I fully articulated this idea in my mind. I’m working it out as I’m talking, right? Because I just, I… marvel at people that can sit in a meeting and they’ve just come up with this like super smart thing to say and, they can articulate this idea. So I just start talking. I’m like, just so you know, like in my mind, my mind’s working as my mouth’s working at the same time. And so if you can sit back instead of, that’s how I found early on is I would do that. And then I’m like dominating a conversation because I’m just thinking. So instead of just like, just let everybody else kind of talk and work your way through this and let’s see if I can bring some consensus together or find some things that fit together. So working, and a lot of that comes with working with younger leaders or people that hopefully I’m helping or trying to help coach or mentor into leaders. So what do you hope the next generation of leaders do better than we do or that we’ve done?

Jenny: Everything.

Barry: You think?

Lindsay: Our mayor says this right now, we’re in a leadership desert. That’s one of the things you hear him say a lot. And I do think it’s because it’s just such difficult work in so many ways. And we’re really hard on our leaders. And we should. We should have high expectations for our leaders. But yeah, I mean, I hope, think like we all do, that future leaders will be better at collaborating with each other and listening to each other and bringing different perspectives to the table. I hope future leaders will do a better job of finding balance in leadership so it doesn’t burn through so many people and instead can be something more sustainable for folks. So it doesn’t feel punishing because so many, I think, do find it that way. Yeah, kinder and gentler. I don’t know.

Barry: Real quick, I guess I’m thinking here. I said a couple of seconds ago that I described myself as an overt thinker and I stated that completely wrong. I describe myself as an extroverted thinker. So rather than being an, I don’t know why I said overt thinker, I describe myself as an extroverted thinker. Maybe. Yeah, I’m certainly not an introverted thinker. I have to like say things loud. Sorry, I was like, did I say that right? Did I not say that right? Anyways, extroverted thinker. Yeah.

Jenny: Yeah, I was thinking leadership as in the school context. And I was just thinking about leaders within a school. I feel like future leaders should listen to kids more. So I guess when we go back to the clients question, I guess leaders should just be listening to their clients a little bit more, like the people that are experiencing the thing.

Barry: Yeah.

Jenny: So yeah, collaboration and just listening and they usually have the better ideas. Like kids definitely, definitely, have the better ideas.

Barry: Yeah. I mean, do you think that’s, so, I mean, we’re all generally the same age, generally. Sorry. I mean, I’m older than both of you, so I don’t mean to put you in my age group. I mean, that’s probably just, it’s probably indicative of the types of leaders we grew up around, right? Certainly in the corporate world, I think for me, it was like, there were someone that told you what to do, and you did what they did. And they weren’t necessarily soliciting feedback from other people in order to help get information. It was like, you have the plan, you laid the plan out and you execute the plan. So I mean, maybe that’s changing in general and maybe influenced by people that are younger than me, certainly, maybe younger than all of us, who are now kind of influencing those ideas around leadership and the workplace, right? Having consensus, having more people involved in the conversation rather than thinking that one person has all the answers and kind of just can lead the charge and make the plan. Interesting. So maybe they’re already doing it. So maybe young leaders are just doing it already, already on their way towards that.

Jenny: Yeah, maybe.

Lindsay: Hopefully.

Jenny: A little bit more.

Barry: Yeah, I agree with that. I think younger people that I work with, they’re way better at it than I was at their age. They seem to be smarter about it and like more, they do it more intentionality. They’re a little bit more, yeah, they’re just smarter about the way they do that. Yeah.

Lindsay: But they’re also like, sorry. They’re like we were talking about right before we got on and started doing this officially, like, they’re listening to podcasts, they’re reading books. There’s a lot more conversation about leadership. And the content is out there generally. We didn’t have that when we were kind of emerging in leadership. And to your point, Barry, I mean, there were very defined sort of modes of leadership. And the most common one was the top-down one. It was the cleanest one. So I think that young leaders do have the benefit of the fact that we’re having this conversation a lot more. I mean, we’re doing this today.

Barry: Yeah.

Lindsay: It’s a great example. So like it’s good for them.

Barry: Yeah, it’s true.

Lindsay: That’s a benefit to them.

Barry: Yeah, absolutely. Makes all the sense. So as we talk about leadership, it’s impossible, I think, to separate leadership from culture. Leadership shapes culture, culture shapes leaders, sometimes in ways that we don’t even really imagine until we step back and reflect on it. In my view, culture is most apparent in how people treat each other, how they communicate, how they perform when no one’s really around watching what they’re doing. And I often say that the strongest professional relationships I have are with people that are like-minded individuals, right? They are people who are like-minded and they see the workplace culture as being essential, something that’s essential in building, right? And for everybody that’s around, they understand the culture isn’t about just business, about business outcomes. It’s about leaders creating environments where people feel welcome, where they feel like they contribute, and it provides an environment where they can really flourish. So much like that whole client experience, I was thinking about culture in schools because I don’t have that same kind of experience. And it feels like it’s going to be, it’s way more layered for y’all than what I’m talking about as far as culture and culture building goes. So I mean, again, I assume that culture has to be, or is, shaped by students, by staff, by families, by the community, all those things at once. And so like we were talking about before, unlike strategy or policy, culture isn’t something you can just write down and implement and execute. I mean, it’s something that has to be created, has to be fostered with some intentionality. So in a school setting, how is, I mean, when you walk into a place, can you feel a culture? Do you know what the culture is like when you walk into a building? Can you just feel it like within a few minutes?

Lindsay: Yeah, 100%. I mean, it’s interesting. The school that I taught at for 12 years, I went back there this year, being back in the school district, and I went back there early in the school year to go to a meeting. And I walked through the door and I was like, “bad news, bad news.” You know, you could just, you can, it’s, it is, it’s not, it’s a feeling that you get for sure. And to your point, it’s also a really intentional decision that leaders and that a community makes to cultivate culture. But yeah, we say a lot in education that culture will eat strategy for breakfast. You know, we all have heard that before and it’s so true. Like you, If you don’t start with culture, it’s gonna hurt you in the long run. You also have to break cultures. I mean, I have that experience this past year. There was a definite culture in place and it wasn’t doing anybody any good.

Barry: You went into an existing school.

Lindsay: Yes.

Barry: And became principal at a school that was already existing.

Lindsay: Correct, yeah. And they had been operating in a certain way for a really long time and I don’t think were talking a lot about culture, but culture will emerge whether you intend for it to emerge or not.

Barry: It’s just a matter of whether or not you make some decisions about how you want to direct it.

Lindsay: And I’ve built culture a lot, but this was the first time that I really had to kind of tear it down, and that was hard because because people hang on, even if they themselves can recognize, and this was the case, even when the people that were pushing back could also say out loud, yeah, it’s probably not entirely great. Yeah. It was still about changing how they were going to operate, and nobody wants to do that.

Barry: Yeah.

Lindsay: It was brutal.

Barry: Yeah. Jenny, can feel it? Can you feel the culture when you walk into a place?

Jenny: Yeah. I mean, it’s just kind of what you see. It’s like, what are the adults doing? What are the kids doing? I mean, what does the physical space look like? Is it clean? Is there trash on the floor? What do the walls look like? Are teachers collaborating? Is there a feeling of high expectations? Are teachers talking with one another? Are people gossiping? Are teachers yelling at kids? Are they encouraging kids? Yeah, I mean, the way that people are talking with one another, are people greeting you? Are people smiling? Do people appear to be having fun? Yeah, I mean, there’s a definite feeling. I remember doing a school visit early in my career. We did school visits. They were called 90-90-90 visits, and I can’t remember what the 90-90-90 stood for. It was like 90% free and reduced, and they were 90% proficient and advanced. They were scoring really high, but they were really high poverty schools, and then there was the third 90 stood for something. visited the school, and I just remember leaving the school feeling so sad. It just felt like a prison. That’s what the culture felt like in that school. To me, it felt so sterile and cold, and the kids just were like robots. And I guess that’s how they got the high scores. I don’t know, so compliance-driven, but But like I do, like I can say, like when people walk into our school, there is, I mean, people make comments like immediately people can feel the warmth and like there’s people like speak to our culture like all the time.

Barry: Yeah, it’s interesting, I guess, because with, I mean, at a school, I guess in a professional setting, if you’ve got, when I go to another company. I’m going to see client partners. I’m walking into a financial institution and I’m going into a conference room and maybe I’ll see some of the employees or I’ll go to somebody that we’re working with. I guess in a work environment, you can kind of encourage your employees to put on a good face, right? If somebody’s coming in, put on a good face. You can’t do that with kids, can you? can’t tell like the entire student body. Somebody’s coming here today, everybody put on the good face, right? So you’re going to, you’ll feel that because you’ll probably be totally reflected in the way the kids are reacting and the way that they’re acting. And you probably just get a, I never thought about that. Yeah, they’re not going to fake it. They have no reason to. And they wouldn’t, even if they did have a reason to, right? So you’re pretty genuine. You can feel it just by the kids. Interesting. So what kind of culture do you strive to create and foster and build in your schools? Or have you?

Jenny: I mean, I just, I thought of a few words. I mean, I said friendly, happy, safe, nurturing, creative, organized, bright, calm, fun.

Barry: Yeah. I mean, I think those are things that are, I mean, that should be, that should translate to just about any workplace, right?

Jenny: Yeah.

Barry: I mean, yeah. What do you think, Lindsay?

Lindsay: A mentor of mine, that I’ve worked with now for a while, started talking about hope a lot, and how schools, above all, should be a place where you find hope. And so I agree with all of the words that Jenny mentioned. I think that those, but for me, those all fall under the umbrella of a hopeful place. Like of anything, a school should provide a student, a young person, this idea that they can build something and make something for themselves. ‘Cause that’s what public school is supposed to be, right? Like that was the intention of public school was to give equal opportunity to kids. That was the genius of it. And so I talk about that a lot with adults and with parents and with kids. And I’ll ask kids if they come in and they’re kind of… trying to decide if they want to come to my school, I’ll say to them, well, what do you want from school? What’s your dream for school? And so often, they will say to me, no one’s ever asked me that before. And like Jenny said, it’s just kind of astounding how we just, we’re not listening to kids and what kids want. Because if we… If we just listen to what they want, that’s what they want. They want some sort of the seed for their life that’s going to give them hope. Yeah.

Barry: So culture, I think, it’s a powerful thing, right? And it’s not static. It’s shaped every day. It moves around. So that brings me to something that we’ve talked about a lot over the years. Again, probably informally, and this goes back, I mean, one of you, I can’t remember, mentioned Brene Brown, right? So that whole idea of vulnerability, and that term vulnerable gets thrown around a bunch today. Thought leaders talk about it all the time, and I think Brene Brown was really the person that really kind of introduced it into the professional vernacular, at least, formally, a dozen years or so ago. So everybody talks about vulnerability, but I’m not sure we all really understand what it means, or perhaps it means different things to different people. And so I was, when I was thinking about this conversation, I remember having a conversation with you, Lindsay. I remember exactly where we were. We were sitting in a restaurant, and I was talking to you about a situation I had, a classroom situation, when I was in a teaching situation, and I was talking to somebody, and I didn’t have an answer to a student’s question. I can’t remember exactly the circumstance, but I’m sure I told you what happened. And I did some verbal tap dance around it. And you’re like, “Why didn’t you just say you don’t know? Because you’re afraid of being vulnerable?” And I sat there. And then we kept having a conversation. It probably turned to something else. I remember we were at a restaurant. I was sitting in a booth. I’m like, man, I feel like I’m vulnerable. I’m pretty emotionally intelligent. I’m an evolved guy here. I’m like, I can’t believe she said that to me. I am vulnerable. And so, it hit me differently, and when we left there, it kind of set me off on this path about thinking about what you said and vulnerability, and it challenged me to kind of reevaluate the importance of vulnerability and how, in certain situations, being vulnerable isn’t just about weakness, right? It’s about changing the conversation and being vulnerable in a way that makes a conversation turn so it transforms and strengthens the conversation. So I found that as an opportunity to be able to do that more and more often. So I mean, going back to that original, that original statement about vulnerable, that term being thrown around so much and so often, what does that mean to you in a professional setting? What does vulnerable mean as a leader in a professional setting?

Lindsay: It’s so interesting. We were with our family over the weekend and there were like 25 family members. And so rounding everybody up for an activity or for a meal or whatever is like an act of God. And my husband came out at one point ’cause we were making dinner and he said, I’m gonna use my teacher voice. And so he, ’cause he used to be a teacher as well. And so he said, All right, everybody, you know, dinner’s in two minutes or whatever. And someone said, Is that supposed to be your teacher voice? And someone else, and I don’t even know who it was said, It can’t be the teacher voice. I’m not, I’m not freaked out. He wasn’t mean enough. And I was thinking about how, for me, that question of vulnerability is rejecting what we, sort of what we’ve come to understand about teachers, about how teachers are supposed to interact with kids, about what a school is supposed to look like and feel like. Like, why, why can’t we say, no, actually, A teacher isn’t effective because they’re mean, or because a student is intimidated by them or fearful of them. A teacher isn’t effective because they have all the answers, and they never say, I don’t know.

Barry: Yeah.

Lindsay: I don’t know about that topic. A school isn’t great because of X, Y, and Z. There are a lot of different things that go into having a great school. So I think for me, The question of vulnerability in our profession is sort of, is rejecting what we’ve come to understand about what it means to be a school. Like most schools still operate exactly the way they did in 1950. Kids are in desks and they’re listening to a teacher talk. And yes, we have innovation and we’ve got people doing really creative things. And teachers are the hardest working professionals. anywhere. But we haven’t really taken a hard look at that system and changed it much for a really long time. So for me, in my work, a lot of it is the rejection of that. And for me, that is vulnerability. Because I’m having to say, I want to do it in a completely different and new way. And we may fail miserably in doing that because it’s new and different. Because if I just followed the formula, I could probably get into lockstep.

Barry: Be safe.

Lindsay: And be safe and produce the numbers and do what I need to do. But I just don’t think it’s the right thing for kids. So for me, that’s where I’m vulnerable and it’s where I’m asking teachers to be vulnerable.

Jenny: So I’m trying to like line up my very simple answer about what vulnerability is, because to me, like vulnerability is just simply like being yourself. That’s like, that’s what I believe vulnerability is. But I think like what Lindsay was saying about like, how she was describing vulnerability is basically like aligning her values to what she believes school should be. And I think when you are like, when you are trying to just be yourself and it’s just a lot of times when you are faced with an issue And a lot of times when I get upset about things and my emotion comes out, and that happens a lot at school. And I have to disarm myself a lot when I’m in front of a group of people that I’m leading. And I have to say, like, I might cry before I say something. I might cry when I say this, because it makes me feel better to disarm myself.

Barry: Yeah, yeah.

Jenny: But it’s usually when that thing is flying in the face of one of my core values or something. So I think it comes down to vulnerability has to do with something with the things that we truly value.

Barry: Yeah.

Jenny: So, but vulnerability to me is just like, being yourself, like being okay with saying, I don’t know, or I made a mistake, or just being okay with it.

Barry: Yeah, this is a little off track, maybe a little bit, but not much, I think. So I talk a lot with some of my colleagues or people that I’ve met coach and mentor. And one of the things I promote all the time in client-facing roles is one of the things I promote and help them to try to achieve as just be your authentic self, be just, and that’s really difficult for a lot of people. right? So we always talk about, to some degree, we talk about code switching, right? So you can be your authentic self, but I mean, it’s different when you’re home with your kids than when you’re talking to one of our client partners on the phone. But I think it’s hard for people, again, I think it comes with a little level of maturity and some self-awareness until you really feel comfortable enough in your own skin to just say, I feel I mean, I can do this job way better. I can be way more effective if I’m not being somebody that I’m not, right? And so, I mean, I think that speaks to what you’re saying about vulnerability, right? It’s just being able to let your guard down and say, I am who I am, and I don’t have to put up this front and be a different person because it’s expected that I’m supposed to be XYZ in this setting. Is that right? Does that sound correct?

Jenny: Totally. I feel my best when I am. like Jenny leader and not trying to be, oh, this former leader that I really admired and respected.

Barry: Right, right, right.

Jenny: I want to lead like this person that didn’t feel good at all. You can’t lead like that person because I’m not that person. And I’m also not a male and we’ll get to that later, but.

Barry: Yeah. I mean, I think that, and again, I guess, and maybe that’s a product of the environment that professional environment that we all came up within as well. And maybe it’s just, I mean, maybe there wasn’t anybody encouraging us to do that either. So you saw this model and you saw this path and you felt that the way to get to where that person you respected was, to follow that lead. And so I used to say all the time, I was one Barry at home and I was one Barry at work. And I had to kind of mature and grow up and have some crazy things happen in my life before I was able to eventually just go, I’m going to be way more effective if I’m just myself. And I’ll like my job better and I’ll like my life better if I can leave the house and go to work and be me. And I can come home and be that exact same person. And again, maybe young leaders are, maybe people are encouraging them to do that. And so they won’t have to experience that same thing. And they’ll probably be better leaders, at least than I was early on, I would assume.

Jenny: Yeah.

Barry: So I mean, how does that, I mean, I think we talked about this. I was going to ask how that shows up, vulnerability shows up in the workplace. I think you’ve both just already described that, right?

Jenny: Yeah.

Barry: So culture, it intersects also professional culture. I think it intersects with identity and that includes gender in ways that are subtle. It’s powerful. Sometimes it’s invisible to people who don’t have to navigate those dynamics, right? So before, I mean, we wrap up, I want to shift real quick into a topic that’s, I think, important. And it’s discussed often. I don’t think it’s discussed often enough. And that’s gender and leadership. And so as a guy who’s guiding this conversation, I’m aware that I see leadership through my own lens, right? It’s shaped by my experiences. It’s shaped by my opportunities. It’s shaped by my biases, my blind spots. So that said, many of the client partners that I work with are women. It’s very, very normal. It’s very predominant in financial institutions. And I was thinking about this. Every boss I’ve had before my current boss was a woman as well. So I don’t think I’ve ever really thought about it all that much, gender and leadership, I just haven’t. I know that there’s people that I’ve worked with in a professional space, men, men that are older than me, that would not have been able to, I say, they would never have been able to survive working with that individual because it was a strong female in a leadership position who was a client partner. I was just like, they couldn’t do that. They just wouldn’t be able to do that. So, I mean, you’ve both navigated leadership as women in environments which I guess haven’t always been designed with you in mind. And I know that there are dynamics and expectations and pressures you both have to manage, and that I’ve never had to think about, right? So as a guy guiding this conversation, what questions about gender and leadership have I not asked that I should have asked at this point?

Jenny: So I thought about this a lot because I’ve thought about this a lot over the course of my career because one of my early principals and a lot of, well, a lot of our like zone superintendents and stuff are males and It is different, very different. In a school setting, especially elementary, because most of the teachers are women. So leading a group of women predominantly by like one sole male, it’s like a very interesting dynamic. I don’t know how to explain it, but it’s kind of weird. But I was just thinking, and this is kind of a selfish question, because I feel like I’m a little different. And this kind of goes back to what you were just describing about the two selves and just trying to be yourself at home and work. But this is kind of what I was thinking. I said, I often wonder if we are judging leadership behaviors consistently, or is there a profile? I’m thinking, is there a blue suit, CEO, charismatic, direct, decisive, quick to respond? There’s this profile of this leader, the old school leader, this male that’s this charismatic guy, and he can make decisions quickly, and he’s very decisive. And are we comparing all leaders to this guy? I’m just thinking about this guy constantly. And I don’t know if it comes from my own insecurity, because I always feel like I’ve been opposite of those things. Like, I don’t wear a blue suit, obviously.

Lindsay: You show emotion?

Jenny: I do show emotion.

Barry: You’re pretty charismatic.

Jenny: I take time to make decisions, all those things. So I don’t know if that’s a male, female thing, but I’m constantly thinking about this male in a leadership position. And I do think that whether it’s a male or female, even if it’s a woman in a leadership position, we are constantly like a good leader has those leadership qualities. And I do think that they are more male qualities. I don’t know if I should say that or not, but they’re more masculine qualities, I guess I should say. I’m sorry.

Barry: So you think that the expectation is that a woman that is in a leadership role, you feel that often that the expectation is for them to have those same kind of attributes that a male leader would have.

Jenny: Any leader.

Barry: Got it, got it, got it. Yeah, I wasn’t sure if you’re saying that would be an effective leader or just that you think that that’s there.

Jenny: I don’t feel like that’s effective leadership. I mean, of course, those are effective leadership qualities and other things.

Barry: Yes. What other things?

Jenny: I’ll let Lindsay answer. And then, I mean, I mean, there’s so many things. I mean, there’s so many things that leaders have to do.

Barry: Are there any things, are there any qualities? Okay, so you’re, so you’ve got this, what would it be, this archetype, right? Of like this male leader. And you surely have like these qualities and traits that are attributed to that individual. Okay, or to male, to men in general, what are, if you have the archetype of like this female leader, what innately, I mean, innately is probably the wrong word, kind of female qualities do you think should be incorporated to kind of make this holistic, right, leader, which incorporates those characteristics of this archetypal male leader and this archetypal female leader? So I guess what I’m saying is, what, I mean, as a guy, what kind of traits that maybe are assumed to be more female traits would be better for a male leader to adopt to be a more effective leader.

Jenny: Well, someone who takes time to listen, someone who’s collaborative, someone who is nurturing, someone who is caring. Not that males are not these things.

Barry: Right, right, no, I think that’s interesting.

Jenny: But in leadership positions, in my experience, they aren’t.

Barry: Right.

Jenny: They don’t take time to develop relationships. And I don’t know if that’s a biological thing or– I don’t either. I don’t know.

Barry: But it doesn’t fit the archetype.

Jenny: No.

Barry: Right. It doesn’t fit the archetype.

Jenny: Yeah. But women are just really into developing relationships. You have to develop the relationship first so that there’s trust there. And when there’s trust there, I will do a good job for you. Men don’t care. They’re just going to do the job. The male teachers I’ve worked for, We don’t need to talk about my weekend or you don’t need to know about my family or whatever. They’re just going to do the job, I think, unless you’re more of a– I don’t know. So I don’t know.

Barry: Yeah.

Jenny: A little bit different.

Barry: What do you think, Lindsay?

Lindsay: Oh my gosh, complicated. No, it’s OK. I just think this is so complicated. I’m worried about opening my mouth and just a bunch of word salad coming out because I don’t really know.

Jenny: I just word-salad’d.

Barry: No, you didn’t. No, you didn’t. No, you didn’t.

Lindsay: I think– I just think that it’s just so tricky and complicated and layered. I do think that Jenny makes a really good point, though, that– well, this is how I sort of heard it or am thinking about it. Where I see women leaders getting themselves in trouble is when they try too hard to emulate that picture of leadership that’s been defined for us, that guy, that guy leader. I think we’ve seen that on all levels. Like, I don’t want to go down the road of politics, but this is where I think Hillary Clinton got hung up. Like, she was playing the boys’ game, but she was not built for that. She didn’t operate that way, and so she just came off horribly. It was, like, this terrible look. But I bring her up because I think– I think I see women do that. Um, I’ve only worked for one female superintendent, And I, I really saw her making that mistake. She was not, she was trying too hard to play the rules that the boys club had lined out for her. And it was counter to who, who I think she probably was at her core. And so she came off as very inauthentic and, you know, not approachable and, and therefore, and I think probably didn’t feel good in her own skin. And so then her work performance wasn’t good. And so I think we put those barriers up for ourselves. But I think for me, the challenge as a female leader has been in like the day-to-day operational side. So I’ve had male colleagues say to me, like, we’ll be talking about something, a difficult conversation or there’s a difficult decision to make. And I can remember my male mentor saying, What you just said, you have to say that exactly like you just said it to me. You have to say in our meeting tomorrow. And I said to him, I can’t say it exactly that way. And I can’t explain to you why I can’t. Like, you could use that very same language. You could say it that way. And you were still living in a world where you would be seen as assertive and decisive. And he’s taken the bull by the horns and all that other stuff that Jenny sort of alluded to. But I will be seen differently.

Barry: Yeah.

Lindsay: And no one will say it out loud.

Barry: I know exactly the word you’re thinking that you would be– that they think you are, right? That’s what you become, right?

Lindsay: Right, exactly.

Barry: Yeah.

Lindsay: And we’re still there. It’s interesting, though, in education, we do, when I look around at our district leadership team, I would venture to say there are far more women in the room than men, which is interesting to me. But in upper levels of leadership, it continues still to be men. So I think for me, we just have to in certain rooms, in certain conversations, and in certain situations, we have to edit ourselves in a way that men don’t. And it can be tiring in that way. Like, I find myself sometimes sitting in a meeting and thinking, should I say the thing that is in my head? And many, many, many times, believe it or not, I don’t. And I, you know, Jenny and I worked in the same school district at one time, and a male leader said to me, Man, your parents did not raise shrinking violets. And I said, No, they did not. But he was a person that we both, I think, trusted and felt safe talking to, frankly. But I just wonder sometimes if my male colleagues have to go through that same sort of, like, Can I say this or can’t I say this? I think they can. I think they have permissions that I don’t have.

Barry: Yeah, well, also, I mean, I think you’re speaking to this. So that’s one of the things I was going to ask is, what do you wish your male colleagues understood better about supporting women leaders? I mean, these are great insights, obviously. I mean, for me, they are even. So I mean, I don’t think they’re things that I wasn’t fully aware of to some degree, but they certainly weren’t anything I’ve ever heard anybody articulate. But certainly not any of my… female colleagues?

Lindsay: I think if I had a magic wand, we’ve given men and male leaders and just the world that’s been run by men in general, we’ve given them so many passes along the way. I just feel like women deserve the same level of grace or level of forgiveness, right? Like, we’re human, too, and we’re going to misstep in a way that you might not understand or– but can’t we just have the same– Like, we don’t get the same, I feel like we’re, to go back to the vulnerable, we’re more vulnerable to saying the wrong thing, doing the wrong thing. Like, my career feels more fragile in that way than the men around me. Like, I won’t be given the same pass as a man. Maybe I’m wrong. I mean, maybe I’m wrong. But it kind of feels like maybe I’m not.

Barry: So if your male colleagues understood that, I hate that somebody just said recently, why do we use manifest so much? If your male colleagues understood that, how would that, what would that manifest into? Like if they understood that more, would just be a level of, some level of understanding or sympathy? Or if they understood that and you knew they understood that, would that give you more freedom? to say the things that you want to say? If you had some sort of, if you had a better understanding that your male colleagues understood that you felt that way, would that give you license to be more open?

Lindsay: Yeah, I think it would. I mean, if like in a perfect world, if we sat down and we all made agreements ahead of it all, ahead of the work to say, we’re going to operate differently, we’re going to approach this differently, but we just all need to know that we can be in the room and operate the way that is really just true to us without it feeling threatening, maybe that would be great. But I don’t even know how to get my head around that because I’m so accustomed to editing myself.

Barry: Yeah, I mean, I think sometimes you have like there’s meetings, I mean, at least ones I’ve been in. where it’s like, hey, we can say anything here. every, this is open dialogue and just say whatever you want. No one will hold any, you know, we’ve got to get this, we get this worked out.

Lindsay: So let’s just open dialogue here.

Barry: So I think what I’m hearing, but as a male, I may take those instructions and take them genuinely and act upon them, but you may hold back, even though that’s being expressed because the thought is, I know you’re saying this, but I’m not sure I believe that. Correct?

Lindsay: Yes.

Barry: Yeah.

Lindsay: I think so.

Barry: Jenny, what do you think? Is there, if male, what would you want your male colleagues, what do you wish they understood better about supporting women leaders?

Jenny: I always advocate that women leaders have mentors that are also women. So I think it’s valuable for women leaders to be just have another woman to be able to learn from. I don’t know, just because I don’t think that men get it and no shade on them. Like we both worked for the same male leader in the district that we work in right now. And he’s awesome, like great leader. He’s amazing, like super supportive, great leader, great former principal. But he doesn’t get it. I mean, and why would he?

Barry: Yeah.

Jenny: It’s more the– for me, it is like what Lindsay was describing. You cannot say the same things that men can say. Like, I said that to my former principal, who I worked for like 10 years ago. Like, I would never get away with saying the things that you say in meetings. Like, or to staff, like the things that he would say to our staff that they would just be like, oh, Or staff would be like, oh, my gosh, I love how Dustin is so direct, and he’s so– like, his expectations are so high. And I’m like, if I ever said that to a staff, like, they would hate me.

Barry: Yeah.

Jenny: Like, I would always have to, like, couch it with something that’s like, and I love you guys so much, but I would never lead that way, like, the way that he did, but if I ever wanted to, like, people hate me.

Barry: Yeah.

Jenny: So I mean, it’s just so interesting. And it’s weird. And it’s like reminds me of the Barbie movie, like where she– I don’t know where she– have you seen it?

Barry: Yeah, yeah, yeah.

Jenny: Where she’s like going off about how women have to be all these things and that they’re opposites.

Lindsay: And it’s like– I didn’t want that to be– Yes, I love that. I didn’t want that to be so true, but it was actually so true. I’m actually going to So I actually like when I have a male supervisor. So to Jenny’s point, we have the same supervisor. I sometimes feel protected by that because I get to know them really well. And I feel like if there is a situation where I have to be defended, he will he will advocate and say, But that sucks.

Barry: Yeah.

Lindsay: Because I have to count on that. Like he’ll say, yeah, but you don’t get the way that Lindsay really operates, but I do. And here’s what’s really behind that. But the fact that I need, yeah, that we need that layer and when he never would is like the part of the reality that’s kind of shitty.

Barry: Gross. Yeah. Well, I guess, I mean, that’s super, I mean, believe it or not, I mean, maybe there’s no reason you shouldn’t. That was super, that’s super eye-opening for me to hear that. I mean, it really is. And I think I’ve been fortunate in my career, I have been throughout my career, that I’ve had mentors that were both male and female. So I think I’ve gotten a little of both of that and maybe that’s helped me formed like who I am. Maybe it makes me a little bit more open to building relationships and being that way. I don’t know. Yeah, that’s awesome. I think it’s important. I think it’s valuable. I don’t think we talk about it enough. And I think it’s valuable. All right, so we’ve covered a bunch, leadership, culture, vulnerability, identity, all of it ties back to the human side of things, right, and the work you do. So finally, as we wrap up, I’d like to ask you both a couple of more personal questions. that I like to ask just about anyone. So these are questions that I ask colleagues, I’ll ask partner clients. They’re usually questions I’ll ask like a fellow business traveler if I’m sitting like at a restaurant bar and someone strikes up a conversation with me. Typically, I’ll like try not to talk to anybody because I just want some peace. But if it happens, I talk to somebody, I’ll just, I just got these stock questions. So I’m going to ask you these questions if you don’t mind answering. So what’s your favorite part of your job?

Lindsay: My favorite part of the job is the kids. I love teenagers and working with teenagers. And I think they’re funny and interesting. And helping them realize their hopes and dreams is– it sounds really cheesy, but it is the favorite part. It’s my favorite part.

Jenny: Yeah, the kids.

Barry: I mean, it’s almost too easy. That’s like a layup for both of you. Yeah.

Jenny: It’s the, I mean, elementary school. It’s, I mean, Lindsay would say high school, and that’s why we’re in the positions we are, but. Yeah. Yeah, the kids are awesome.

Barry: Yeah, that’s a layup question. I didn’t even think about that. I mean, if you’d have said “ my office” or something, that’d have been terrible. Like, you’re in the wrong profession if you didn’t say kids, I guess, right? Yeah.

Jenny: I mean, I always say I’m grateful that I’m in a job that keeps me active. I love that I’m in a job that I’m moving. I get to see different people. I get to be outside if I want. It’s pretty cool.

Barry: Yeah, I get that, for sure. So if you could reach back and give 25-year-old Jenny, 25-year-old Lindsay one piece of advice, what would it be? Professionally or personally, either way, whatever.

Jenny: I was thinking– so this came to me later in my career, probably the last five years. The idea of that my job is craftable in that you don’t have to go to work and be bummed out. Like you can decide the parts of your job that you really love and lean into those parts of your day. So like when I go to work and I’m kind of grouchy, I will like listen to like 90s rap on my way to work. But then once I get to work, I… spend time in kindergarten classrooms. I go out to recess. I go into my favorite classrooms with my favorite kids. And I get to spend time in my favorite pockets of the school. And I just get to craft my day.

Barry: And that’s something as a 25-year-old you never would have understood?

Jenny: Well, I never– no, I didn’t.

Barry: Yeah. And if you’d known that 25, do you think the first– 10 years of your career would have been different, more enjoyable.

Jenny: Yeah

Barry: That makes total sense.

Lindsay: Oh, gosh, I’m going to steal that. That’s so good, but it’s so true. And we do have, I think, in some ways, more flexibility than a lot of professions have that we can do that. We have less flexibility in other ways. Like, yeah, the screaming eight-year-old or the– 17-year-olds who are beating each other up in the hallway are not going to– you don’t get to, like, put a pause button on that.

Barry: Yeah.

Lindsay: Gosh, I don’t– I don’t know. I think, for me, I probably would– this is sort of– this is sort of cliche, but I– we talked about it earlier. I think I would– I would trust myself more and trust my instincts more. I would try earlier practicing how to speak my mind and advocate for the things that I thought and what I wanted. I think I let a lot of things sort of happen to me rather than taking control of things. I think that’s common when we’re young, because we don’t have the confidence or the wisdom or the whatever to do that. But I think it’s one of the things I’m trying to do in my mentorship. of young leaders is to encourage them to step into things bravely and understand that it will go wrong sometimes, and that’s OK, at least while I’m your supervisor. And you may have to change how you operate if you work for somebody who operates really differently someday. But at least for now, this is a good place to practice and screw up and figure things out.

Barry: So use your instinct more, trust your instinct. Okay, one last one. So do you have a daily hack or a personal hack or a habit, professional, personal, doesn’t matter, that you’d be willing to share?

Lindsay: This has been on my mind a lot because I’m going to emphasize this with my staff this year. But for me, it’s really about my routine. Like we just talked about how we can have flexibility, but I also rely pretty heavily on my like my beginning of the day routine. And we work with a population of kids who lack that in their life, like unlike really affluent families and households where, the family calendar is on the fridge and you eat oatmeal every morning and dad goes to the gym and blah, blah. We’re working with groups of kids who have, who live in kind of chaos. And so I’m really going to try and emphasize how important it is to be able to count on some things. So the fact that I can count on getting to work, setting my stuff down, making a cup of coffee, and walking the building and saying hi to everyone that I can. If I miss that, then it sort of screws up my day. So finding the things that I know I really want to kind of count on every day as a routine is a hack for me.

Barry: Yeah, routine. Easier said than done, right? It sounds easy. Like, I’ll just set these things up, but there’s always a monkey wrench, right?

Lindsay: Oh, yeah.

Barry: It throws you off.

Lindsay: Oh, oh, yeah. I mean, yeah, if there’s an irate parent sitting outside of my office who’s there to tear me apart or tear the school apart for something, like, I don’t get that luxury. And that’s a crappy way to start your day, but That’s part of the job. The part that sucks about it is it disrupted that thing that I count on.

Barry: Yeah, interesting.

Jenny: Mine is similar. So I started doing this, actually, this year. So I try to– I do the morning announcements for our school. So after the morning announcements, I immediately leave my office. And I go and personally, physically touch. it’s usually like five to six of our highly impacted kids. I go into their classrooms, and I put my hands on them and look them in the eyes and say good morning. And I want to put my hands on them. And I swear, like we talk about manifesting things, I swear when I’m able to do that, they have good days. And on the same note, I really try to make it a– but make an effort to get to four to five staff members. And I really do try to systemize this. I don’t, I wouldn’t ever say this to staff, but like I do try to have like personal conversations with like four to five staff members, like not about school stuff, like about their kids, their husband, their weekends, just like personal stuff, like just that relationship, like connection building time.

Barry: So that being a hack, how does that? How does that help you having those conversations?

Jenny: Well, it just helps me feel good and connected to staff. It makes me feel like a human being and not just like a administrator.

Barry: Yeah.

Jenny: It makes me feel happy because I know that they’re like, oh, she’s not just in here to do like an evaluation or like to give me feedback about something or, oh, she cares about me and I do care about them. And it just makes, I don’t know. I’d like to– Yeah, it builds culture and it helps the school. And I don’t know, it just makes me feel like I’ve been able to step away from work a little bit.

Barry: So it’s effective for you personally, and at the same time, it has the benefit, assumingly, of being effective in the folks that you work with and your colleagues feeling better about their workplace as well. That seems pretty simple, right? I just like to go talk to three or four people. That doesn’t even sound like it should be a hack. It sounds like it should just be a habit, right?

Jenny: Or something that you do. You just get so busy.

Barry: Don’t get me wrong. I totally agree with it. It is a hack, but it doesn’t seem like it should be a hack. Or that it should have to be a hack.

Jenny: Yeah, it is crazy. Yeah.

Barry: Cool. Well, Lindsay and Jenny, it’s been a pleasure. I appreciate it. The dog barked a couple of times up there. It wasn’t too bad. Yeah, I appreciate you both greatly for being open to having this conversation with me. I know it’s a bit more formal than our normal conversation, so I thank you both for being open, willing, thoughtful with your time. I just wanted to introduce you to other people. So before we part, any final thoughts that you’d like to leave with people? Anything you want to say?

Jenny: Thanks for having us, Barry.

Barry: Speechless.

Jenny: Lindsay’s never speechless, so Linds.

Lindsay: I think this is awesome. I think it’s a great project. Pay it forward, people. Yeah.

Barry: Well, thank you both very much for taking time out of your day. You guys are kind of officially on summer vacation, so this is doing something that’s almost work-like. So I appreciate it. Thank you both very much. I appreciate it.

Jenny: Thanks, Barry.

Barry: Yep.