June 2, 2025
Episode 31: The Road to Awesome: Dr. Darrin Peppard's Journey on Purposeful Leadership, Culture, and What Truly Matters!
Fan Mail! Dr. Darrin Peppard's educational leadership journey began when his college roommate asked for help coaching fifth-grade basketball. That simple moment sparked a passion that would guide him from classroom teacher to award-winning principal, superintendent, and eventually to becoming one of education's most respected leadership voices. The turning point in Darrin's leadership philosophy came during his first year as an assistant principal while processing over 2,200 discipline refer...
Dr. Darrin Peppard's educational leadership journey began when his college roommate asked for help coaching fifth-grade basketball. That simple moment sparked a passion that would guide him from classroom teacher to award-winning principal, superintendent, and eventually to becoming one of education's most respected leadership voices.
The turning point in Darrin's leadership philosophy came during his first year as an assistant principal while processing over 2,200 discipline referrals. During a contentious staff meeting about enforcing rules on hats and cell phones, someone asked, "Why does it always have to be about what they do wrong? Why can't it be about what they do right?" This question fundamentally shifted his approach from punishment to celebration, from compliance to culture-building.
What makes Darrin's insights so valuable is how he transformed this philosophy into practical action. Rather than imposing solutions, he assembled diverse teams of educators and students to identify root causes of problems. When investigating poor third-period attendance, students revealed they were skipping because they were hungry after being forced to throw away breakfast items at the door. Simple solutions like strategically placing trash cans dramatically improved attendance. His commitment to making everyone feel "seen, heard, valued, and trusted" ultimately raised graduation rates to historic highs.
Now through his company Road to Awesome, Darrin coaches educational leaders to get clear about what truly matters to them, be intentional in their actions, and lead with purpose. His bestselling books "Road to Awesome: The Journey of a Leader" and "Culture First Classrooms" (co-authored with Katie Kinder) provide actionable frameworks for building positive school cultures. As Darrin explains, effective leadership isn't about perfection—it's about clarity, intentionality, and focusing on relationships first.
Ready to transform your leadership journey? Connect with Dr. Peppard through his website roadtoawesome.net, subscribe to his Leaning Into Leadership podcast, or join his email list for weekly insights that will help you move from crisis management to purposeful leadership. The road to awesome begins with a single step—what will yours be?
Connect with Dr. Darrin Peppard by clicking on the links!
Road to Awesome Book (Amazon):
Culture First Classrooms Book (Amazon):
Leaning into Leadership Podcast:
Connect with Principal JL Click Here:
Want to be a guest on Educational Leadership with Principal JL?
Send Principal JL a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/1742787866678447e5bdb89c1
01:57 - Introduction to Dr. Darren Pepperd
03:38 - Finding His Path in Education
06:11 - First Years in the Classroom
11:12 - Transition to School Leadership
19:23 - Building Positive School Culture
30:44 - From Principal to Superintendent
39:20 - Writing Road to Awesome
46:07 - Culture First Classrooms Book
51:43 - Current Work at Road to Awesome
59:26 - Closing Thoughts and Contact Information
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Today I am thrilled to welcome to the show Dr Darrin Peppard.
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He is a dynamic keynote speaker, leadership expert and consultant who is passionate about school principal and superintendent.
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Darrin brings a wealth of real-world insight and inspiration to the table.
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He's the best-selling author of Road to Awesome the Journey of a Leader, and his latest book, culture First Classroom, where he co-authored with Katie Kinder, is already making waves for its powerful message on leadership relationships and classroom culture.
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Darrin is also the host of the Leaning into Leadership podcast, where he shares practical and actionable wisdom on building strong teams and thriving school cultures.
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Now here is my conversation with Dr Darrin Peppard.
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Welcome back everybody to another episode of the Educational Leadership Podcast.
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Today I have Dr Darrin Peppard in the house.
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Welcome, darren to the show.
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Yeah, absolutely Thanks, jeff.
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I appreciate it,
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All right, Darrin, I'm going to ask you the same question I ask everybody.
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Yeah, it's an interesting story because, coming out of high school, the last thing I would have told you I would be was a teacher and honestly, in college I kind of struggled.
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I bounced from one major to the other.
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I mean, I actually started as a physical therapy major and very quick story on that.
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When I was a sophomore in high school I was on the basketball team.
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I'm in the training room.
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It's Thanksgiving break.
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It's that Friday after Thanksgiving.
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I'm in doing some rehab on an ankle injury that I had and Doug Flutie throws this miraculous pass to Gerard Phelan to beat Miami Boston College in the Orange Bowl.
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And I saw it on TV in my trainer's room and when I had to choose my first major, I'm like, hey, trainer John's got a really cool job and he's got a TV in his office.
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I want to do that.
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Well, that didn't work out and honestly, there were three or four other majors along the way and I just couldn't find that calling for me.
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And a buddy of mine, one of my roommates in college, came home one day and he said hey, would you come help me coach this basketball team?
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I kind of got roped into doing it.
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I was a wrestler in high school.
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I don't know what I'm doing.
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Will you come help me?
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I go to basketball practice with them.
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The next day, jeff, I was hooked.
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I was like, oh my gosh, this is what I want to do.
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I want to work with kids.
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And it wasn't like it wasn't high level basketball, it wasn't the X's and O's that got me, this was fifth grade girls basketball.
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So it was like bumblebee basketball, like everybody swarming with the ball.
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That wasn't the thing.
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It was.
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Wow, I want to work with kids.
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And went and saw my advisor the next day changed my major for that next semester and all of a sudden I had a focus.
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I had a direction.
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I wanted to work with kids.
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I wanted to be a head basketball coach, a goal that eventually I achieved.
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But really it goes back to that moment in time such an odd way to find your path in life.
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But, man, I was.
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I was absolutely hooked.
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I love coaching kids.
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Yeah, I know that's kind of some very similar to my background, my story.
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It was really coaching that got me into becoming an educator, so that's something that you and I both share.
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So let's talk about you know you found your passion here.
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You want to be an educator.
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Let's talk about getting into the classroom.
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What was the classroom like as a teacher?
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What are some things you learned just about yourself or about just the profession as you were teaching?
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I love this question because this is one nobody ever asked me.
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When I started as a classroom teacher, I wanted to be a high school teacher.
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My major was secondary science and I really wanted to be a high school biology teacher.
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I wanted to be a high school teacher, my major was secondary science and I really wanted to be a high school biology teacher.
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I wanted to be a head basketball coach and the offer that came was a middle school job and I thought, man, there's no way I want to.
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I would.
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Actually, that particular school was a junior high.
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Like man, I don't know that I want to teach junior high.
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Man, I don't know that I want to teach junior high, but I'm a Wyoming kid, grew up in Wyoming, and when you grow up in Wyoming and you go to school at the University of Wyoming, more than likely you develop a complete disdain for icy, cold weather, and so when this offer came at a school in Northwest Arizona, I jumped at the chance and when I first got into that classroom, first off my principal, betsy Parker love her to the end of time, one of my greatest mentors she hired me to teach seventh grade life science.
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I was excited, I'm going to come in I get to teach biology.
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I mean, yeah, it's seventh grade, but that's okay.
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I'm excited I get there and I find out I'm actually going to teach eighth grade physical science, which is not a strength of mine, and eighth grade math, which I'm probably the last person who should be teaching a math class.
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Um, so I mean, the lesson started before kids even walked in my door and I think, like for for many teachers, especially who started in the mid nineties, it was here are your keys.
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Good luck.
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And in the corner of my room there was a stack of textbooks, and I didn't have any math textbooks, so I had no idea what I was doing there.
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Luckily I had a couple of weeks to prep for that.
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But what I discovered, I think more than anything no-transcript I've carried through my entire life it's about relationships.
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You know old relationships with your kids, and that was one of the things I really leaned into.
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And you know, I remember that that first year as a classroom teacher, my very first formal observation happened to coincide with when I did my very first discipline referral.
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I had a kid who was mocking me and mimicking me the entire time.
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I finally had to ask him to leave and send him to the office, and my assistant principal that was doing the observations, like man, you have got the patience of a saint.
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I'd have kicked him out a long time ago.
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What are you doing?
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And I just I've worked really hard to build relationships with my kids and now, jeff, that's almost 30 years ago, there are a whole lot of those kids I still have a relationship with to this day.
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And when you do that, I think that is what sets you up for success as a classroom teacher, as a building leader.
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No matter what it is that you do, if you focus on the people, you focus on relationships.
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I think that's probably the number one thing I learned.
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I don't think I necessarily figured it out right away, but because I felt like I was overwhelmed with all these other things, I knew I was good at building relationships, so I really kind of leaned into that.
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Oh yeah, you're speaking my language there about building relationships.
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I think that's really key, no matter what capacity and education you're at if it's, you know, a paraprofessional, if it's, you know, a classroom teacher, you know administrative, assistant, principal, any role you are in education it's about building up those relationships, because there's things that you'll you don't know your impact until later impacts that that person until much later.
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And when you get those phone calls or those letters or those emails about how you impacted them because of something that, hey, it was just because that's what you do, that's your, you know you, you know just building that relationship, just who you are, um, how it impacts somebody down the road is powerful.
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So that's really, uh really.
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Thank you for sharing that piece of advice there with people.
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Now you always talk about you know you've been teaching for a while and then you go into becoming the principal.
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Everybody calls it the dark side, but I still think you know we have to look at it as we're all working together right, even though people like to call admin the dark side on things.
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But so talk about you know that transfer or that you know transformation from teacher into administration.
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What motivated you to take that leap?
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You know, it kind of goes back to I think it was either my second or third year as a classroom teacher.
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I'm almost positive it was my second year.
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There was a moment in time, my first principal again Betsy man, she had made such an impact on my life.
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But there was a moment in time it was during the summer.
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I was in the main office and she was there and she just kind of pulled me aside and said you know, you really ought to think about a career in school leadership.
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And Jeff had never crossed my mind.
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I mean, that is not, you know, and and the same kind of thing.
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Right, you know, I come in as a, as a new teacher.
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Um, on my prep there was a traveling teacher that that Betsy told me later.
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She intentionally put him in my room because you know he's a veteran, he can kind of, you know, guide and support me and that kind of stuff.
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And and he probably, along with the rest of the you know, the coaching staff and all that kind of stuff, helped me form that dark side mentality of administrator, bad and um.
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But but when Betsy tapped me on the shoulder and said, hey, you ought to think about this, that kind of opened my eyes and when I first arrived in the state of Arizona, the way the licensure worked in Arizona.
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You had eight years from the time you got your initial teacher's license to complete a master's program.
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It was a requirement in the state.
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They ended up doing away with that a few years later, but I was getting ready to start my master's program and I had a student teacher, and so when you get a student teacher, a lot of times the university that you do this through will give you complimentary courses.
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And so I ended up having, I think, my first four courses paid for it because I had two student teachers in a row and I went ahead and started in the administrative, you know, licensure program and I think I had this moment where at this point, I was a head coach and I had, you know, I kind of had achieved what I really wanted to achieve.
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I wanted to be that head basketball coach and we're starting to have some success and starting to grow a really strong program, and I felt like I kind of had one of those two roads diverge moments for me and I had to make a choice, you know do you just continue with the coaching I had finished my master's degree or do we go ahead and pursue the school leadership avenue?
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And at this point my daughter was five, six years old and my wife and I were talking about moving back to our home state of Wyoming.
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And, jeff, I didn't want to go back to or move to another location and get behind other people in line.
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I was a department head.
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I had an absolutely stellar schedule.
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I was the head coach, I mean, I had kind of ascended to where I wanted to be as a teacher and so it was.
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You know what.
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Let's look for administrative roles and I was fortunate enough to land at a high school in Southwest Wyoming as an assistant principal and man, the lesson started right away.
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There's this I don't know misbelief or misunderstanding that when you have the title behind your name, all of a sudden that changes the way things work and it's just not true, just like I did in the classroom, that I needed to really work hard to build relationships.
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You know that that first year I was in charge of all high school discipline and attendance as a high school principal.
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You can appreciate this one school of about, at that time, about 1100 kids all high school discipline and attendance came across my desk.
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So I mean, it was.
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It was just nonstop, you know, catching people doing things wrong, handing out the consequence, and I think, I think I very quickly, maybe even by the end of the first semester, felt like man, if something doesn't change, I, I, I can't, I can't keep doing this, I can't keep doing this job.
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Jeff, I did 2200 discipline referrals my first year.
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I mean, it was seriously non-stop.
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And partway through the year this was really kind of the moment where and I didn't label it that or anything like that but looking back, this is really where Road to Awesome begins.
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We're in this staff meeting and it's the staff meeting, right, the staff meeting, the one where we're going to figure out what we're going to do about the two most important things on our high school campus hats and cell phones.
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Oh, that staff meeting, right, yeah, oh, exactly, right, yeah, yeah.
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And because I'm in charge of discipline and attendance, I get to facilitate this staff meeting and we're I mean, we're all over the place with different consequences and ways we can force them to do what we want.
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And and somebody raised a hand and just said Darren, why does it always have to be about what they do wrong?
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Why can't it be about what they do right.
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And for me, that was a huge shift.
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I mean, I remember just standing frozen in time like, wow, why are we doing it this way?
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Um, I I started showing up a little bit differently after that.
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I mean, there were still consequences for misbehavior, don't get me wrong, but but it was like maybe we need to start thinking about what we're looking for here.
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If all we do is look for negatives, we're going to find it and we're doing a good job of it.
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By the way, I mean, we were really good at finding the bad things, and it wasn't just the kids either, it was the staff.
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I mean, we were looking for things staff was doing wrong and our culture was terrible.
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It really was.
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And for me, I think you know, one of the biggest lessons, as I made that transition that whole first year was what you look for, what you value, what you think is important is what you're going to find.
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And in our case, we were so focused on those negative things, the things people were doing wrong, that we were completely missing all the great things that were happening in our school.
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And making that transition to starting to focus on what was right versus only focusing on what was wrong ultimately made a huge difference in the culture of our school.
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You know you're kind of speaking to that whole.
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You know.
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You know you felt like all you're doing is chasing down all the negatives you were.
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You know, just, it felt like just you're beating people down instead of lifting them up.
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So let's talk about how you did that.
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How did you build your school culture and leading your team as a school ?
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Yeah, no, that's a great question and, honestly, it began with me still in the assistant principal role.
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The very next day after that staff meeting, I had a conversation with our principal and I'm like man Randy, we got a problem, our culture's broken.
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And he said I know.
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He said, but I don't know how to fix it.
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What thoughts do you have?
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And I mentioned to him at my high school, where I'd been a teacher, they had this thing called Jostens Renaissance and they were celebrating kids for doing the right things.
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I'm like maybe we ought to look at that.
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He's like sure, let's check it out.
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I flashed back into that meeting and when that question was asked, those two questions were asked.
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I remember seeing some faces around the room that probably looked just like mine, like well, why aren't we doing that?
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And I went to those people that day and said and I went to those people that day and said I've got an idea.
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Do you want to be a part of this?
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And eight of them said yes almost right away.
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And as a collective group, we started talking about what are the things that we need to improve on our campus and we looked at some key metrics.
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Obviously, you want to go to data, our average daily attendance rate was like 84%.
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It was horrible.
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So, okay, that's an area we need to improve.
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We looked at our graduation rate.
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It was under 70% Horrible, we need to improve here.
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I looked at our testing and we looked at teacher retention and a handful of other key metrics the discipline referrals.
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That's why I know that number by heart.
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But as a group we started saying, okay, let's figure out some steps we can take.
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We're going to go to this big Jocelyn's Renaissance Conference this summer and we'll learn about ways to take some steps.
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But what else should we do?
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And one of the members of the group said why aren't we asking our kids?
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We do this all the time in education.
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We sit around a bunch of adults who haven't been kids in a long time and we think we can solve the problem for kids and to an extent we probably can.
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But why wouldn't we want their voice?
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And we ended up.
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We went through a pretty lengthy process.
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We had a group of almost 100 kids.
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We just asked the whole staff give us the names of kids that are leaders and not just the stud co kids.
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I mean kids who are leaders but maybe don't have a title.
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And man, we had almost a hundred kids that we took through an exercise and through all kinds of different conversations around why this happens, why that happens.
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Like our third period attendance was absolutely terrible.
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Well, I mean, we're looking at the master schedule.
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Like man, what courses are there that the kids hate or what teachers you know that they don't get along with?
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I mean, like, what's what's happening?
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Our kids told us point blank they were hungry.
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You see, teenagers and maybe this isn't true at your high school, I'm pretty sure it is they don't leap out of bed an hour in advance to go eat a nice, healthy breakfast on their way to school.
00:19:26.757 --> 00:19:31.297
No, they come rolling in with their Starbucks or their thing from the convenience store.
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And we had a problem with trash in our hallway.
00:19:34.054 --> 00:19:41.358
Well, my predecessor would stand at the front door with a big giant trash can.
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He wasn't greeting kids, it was throw it away, throw it away, throw it away, throw it away.
00:19:45.955 --> 00:19:47.746
Greeting kids.
00:19:47.746 --> 00:19:49.210
It was throw it away, throw it away, throw it away, throw it away.
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So these kids are coming in with hardly anything in their stomachs, being told they have to throw away their stuff, that they just waited in line, you know, at Starbucks for 20 minutes, for they're skipping third period because they were hungry.
00:19:59.328 --> 00:20:06.938
So we wouldn't have figured that out, but our kids told us here's why that's happening, okay.
00:20:06.938 --> 00:20:09.928
So we put some pieces in place to help with that.
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Number one we stopped meeting them at the front door and making them throw away their stuff.
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We bought a whole bunch of trash cans and we put trash cans where they were needed, took care of the trash problem.
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They weren't throwing trash around because they were bringing their breakfast in.
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They were throwing trash around because there was no place to put it.
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And teenagers are pretty good at just setting their stuff down and hoping their mom picks it up for them, right.
00:20:34.539 --> 00:20:50.451
But just having those conversations with this group of eight, and ultimately we whittled that group of kids down to a group of nine kids that ultimately we called our culture steering committee, and it was a mix.
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It was, you know, and this was spring semester, so we had a couple of freshmen, some sophomores and some juniors.
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We had no seniors because they were getting ready to walk out the door.
00:21:00.894 --> 00:21:04.035
We wanted kids who would be with us the following year.
00:21:04.035 --> 00:21:09.429
We took them along with our crew, we went to this big conference and we were blown away.
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We're blown away with how you actually focus on the things you want to see and then recognize, reward and reinforce them.
00:21:19.472 --> 00:21:25.352
And, man, we made some unbelievable changes in the culture of our school.
00:21:26.434 --> 00:21:27.837
But, jeff, it doesn't end there.
00:21:27.837 --> 00:21:38.855
That really helped us, especially with things like attendance and those types of things, but it wasn't going to move the needle with the academic side.
00:21:38.855 --> 00:21:42.026
We needed to make some changes on the academic side too.
00:21:42.026 --> 00:21:57.862
We needed to really focus on high quality teaching and learning in the classroom and helping our staff move away from that stand and deliver all the time to really engaging students in their learning.
00:22:01.703 --> 00:22:36.068
Among the things that we did, we did a lot of different things, but among the things we did was we started looking at the career pathways that our kids had in mind, things that, for example, in the Health Occupations Academy, that really not only met state standards but also still connected to the interests that the kids had in their potential career field down the road.
00:22:36.068 --> 00:22:38.212
Doing that work.
00:22:38.212 --> 00:22:40.938
Holy moly, what a big difference.
00:22:40.938 --> 00:22:42.467
Kids are going to go to class.
00:22:42.467 --> 00:22:53.738
They're going to go and be engaged when there's something that's relevant to them, and that was part of what we referred to as our rigor, relevance and relationships framework.
00:22:54.586 --> 00:23:01.586
Those three pieces in the classroom really made a tremendous difference and we really started to see some wonderful gains.
00:23:01.586 --> 00:23:24.480
And I think those two things ultimately were what led to me becoming the principal of that school, was leading those two efforts and I'll tell you by the time I left that school, not the numbers we wanted, but 81% and 84% graduation rates my last two years, the highest grad rates in the history of the school.
00:23:24.480 --> 00:23:30.307
So I think so, and again I've said relationships repeatedly.
00:23:30.307 --> 00:24:02.097
Through all of this, when you really work to get people into the mix, when you really work to listen to them and work towards things that make a difference, the collective culture of that school transformed tremendously from let's just use punishment to gain compliance to a place where I think for the most part, everybody felt seen and heard and valued and trusted and that's to me that's kind of the secret sauce, if you will.
00:24:04.826 --> 00:24:06.391
You touched on a lot of things there.
00:24:06.391 --> 00:24:10.689
When you're just after compliance, you're just going to beat your head against the wall, right.
00:24:10.689 --> 00:24:28.166
But when you bring people together, people have a voice, they're heard, you're taking in consideration of what the issues are and you're taking their feedback, but you're not just listening, but you're actually having actionable steps on top of that.
00:24:28.166 --> 00:24:40.019
I think that makes a huge difference in the shift in the mindset of a school culture and how you get people rally around and help everybody be successful in that environment.
00:24:40.019 --> 00:24:48.108
So really, that's really just a powerful story to share with people about how you go from.
00:24:48.108 --> 00:24:53.832
You know we're going to do all these things and I'm going to you know, make you compliant to.
00:24:59.515 --> 00:25:00.215
It was never about me.
00:25:00.215 --> 00:25:16.872
It was never about me.
00:25:16.872 --> 00:25:32.664
It about us, or think that it has to be about us, not necessarily like from an ego perspective, but from a we are the system.
00:25:32.664 --> 00:25:43.785
That's when those things fail, or when that person leaves, they go away, because it isn't about the collective system, it's about just me as an individual.
00:25:43.785 --> 00:25:46.027
This is how I want things done.
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Just me as an individual.
00:25:47.348 --> 00:25:48.730
This is how I want things done.
00:25:48.730 --> 00:25:49.049
None of it.
00:25:49.049 --> 00:25:52.574
The culture focus, the career academies, any of those things.
00:25:52.574 --> 00:25:54.075
They were never about.
00:25:54.075 --> 00:25:55.056
Darren wants this.
00:25:55.056 --> 00:25:57.479
It was about as a collective group.
00:25:57.479 --> 00:26:00.342
These are things we've identified that we want to do.
00:26:05.105 --> 00:26:09.107
I was just really fortunate to be in the position to lead those particular efforts and work around a whole lot of great people, yeah, no.
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And then I am right there with you.
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