It’s one thing to acknowledge outcomes that miss the mark; it’s quite another to intentionally transform them into rich learning opportunities. Listen as Dr. Peter Stiepleman, leadership coach and retired superintendent , shares with Dr. Janet Pilcher the foundational principle of his podcast: the importance of reflective practice.

This commitment to reflection is central to his podcast, An Imperfect Leader, where Peter interviews leaders weekly about decisions they made and what they learned from them. He and Janet then close with a discussion on the evolving landscape of education, including the integration of AI and the enduring value of connection and empathy in leadership.

This episode addresses questions such as:

  • How do we prepare for the future of education? What challenges might be ahead, and how can we plan for them?
  • When decision-making, what does it mean to “engage those closest to the work,” and why is it necessary?
  • How can after-action reviews equip leaders to improve decision-making and create a culture of continuous learning?

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Episode Transcript

Peter Stiepleman: The principal raised their hand and said, “you know, I look around the room and we’ve not engaged one single student about their future.” And so I think about this idea of like, you really have to engage those who are most impacted. 

[Intro music plays in the background.]

Introduction

Janet Pilcher: Hello, everyone. Welcome to the Accelerate Your Performance podcast. I’m your host, Dr. Janet Pilcher, founder and president of Studer Education. 

As a leader, have you ever made a decision that didn’t quite go as planned? When that happens, do you take the time to truly reflect? Do you identify what was overlooked? Understand your role in the system and recognize any good that may have come from it? Well, today I’m excited to introduce to you a colleague of mine, Dr. Peter Siepelman. Through his work, he powerfully encourages leaders to confront these critical questions so they can learn fast and learn often, a skill more important than ever as we navigate the challenges and opportunities in education. 

Peter is an accomplished educator, leader, author, and podcast host, even earning the title of Missouri Superintendent of the Year in 2021. Much like our mission here at Studer Education, Peter’s extensive work is dedicated to helping leaders and organizations foster collaboration, embrace system thinking, and effectively drive change.

Listen today as Peter invites us to embrace continuous learning through deep reflection.

Interview

Janet Pilcher: It’s with great pleasure that I welcome Peter to our show today. Peter, welcome. So excited about our talk today. 

Peter Stiepleman: Oh, Janet, I am so thrilled. I’ve been looking forward to this conversation. 

Janet Pilcher: Absolutely. It’s good to see you at AASA and great to have you on our show. I know you and I have some common connections with superintendents across the country. So our conversation is going to be a good one today. So thank you. 

Peter Stiepleman: Perfect. 

Janet Pilcher: So let’s talk about, let’s start. You have, you host a podcast. It’s called An Imperfect Leader, and you’ve hosted some of our partners on your show. That’s the way we got introduced at AASA. Deeply grateful for what you contribute there, Peter. But tell us a little bit about you, your background, how you went from teacher to superintendent, to podcaster. 

Peter Stiepleman: Oh, you bet. Well, first, I would say it is so true. I’ve become somewhat of a groupie of Studer and your team, and it’s an amazing team. And so over the last few years, I’ve had such a privilege to get to know some of your districts that you work with as well as some of your coaches. So I’m really grateful to be here. 

My trajectory to this work is, well, so sometimes when I’m on the podcast, I will ask people, like, “tell me about your work.” And often it’s, you know, teacher to principal to superintendent. So I started to say, “you know, unless you were in the circus, we’ll just assume that you followed the regular sort of path.” 

My path is a little different. I was an insurance agent actually before I became a teacher. And even before that, I worked at the U.S. Embassy in Madrid, Spain. And I followed love to California and went into the insurance industry and quickly realized that that was– it’s important work; it wasn’t my work. And I had taken some education courses in college and I was in California at a time that Pete Wilson had signed a class size reduction law, the governor of California at the time. And they were really in need of classroom teachers. And because I was bilingual in Spanish, they were in real need for Spanish bilingual teachers. So I applied to a program at UC Berkeley that was quickly training teachers to get into the classroom. And I started working in the Oakland Public Schools. And that was an incredible experience. 

So I went from Oakland to the Midwest after six years because my wife had gotten a job at the University of Missouri. And so I was the trailing spouse. And then I followed that traditional path. I went from teacher to assistant principal to principal to assistant superintendent and then was grateful that the board of education had selected me to become the superintendent of a fairly large district, about 19,000 kids, 3,000 employees, 300 square miles. And it’s rural, suburban and urban. And so I really got to learn quite a bit about the very different perspectives that one brings to a school district. So that’s my story. 

Janet Pilcher: Yeah, that’s a great story. And you know, I love it that you had experiences before being a teacher. My path was a little bit like that. I didn’t start as a teacher. I started in business and industry and then moved to, you know, moved to teaching. But I still go back to some of those roots, you know, some of the basic things. 

Peter Stiepleman: Yeah. It gives you a real perspective, doesn’t it? And I found myself sometimes at faculty meetings going, “yeah, this is pretty good.” [laughs]

Janet Pilcher: Yeah. [laughs] It is. 

Peter Stiepleman: It was always everyone’s favorite, I guess. Like, all right, you keep it down over there. [laughs]

Janet Pilcher: [laughs] Yeah, no, it does. It provides a great perspective. So, you know, just as you have now been hosting a podcast show and you’re reflecting on decisions that leaders have made, you’ve asked what got overlooked, frustrated leaders, learning about the relationships, identifying, you know, what comes out of those experience. Like that’s, you know, you can talk a little bit more than I can about really what your focus is. But why is that important to you? Like, why did you build your podcast? 

Peter Stiepleman: Sure. Well, I’d like to start actually by flipping it a little bit to say what I love about Studer is how deeply reflective that you are with your clients. You mentor and you coach. And so you’re really intentional about building that right culture. 

I think, and I say that because I think one of the pieces that superintendents miss when they’re getting trained, I mean, we go to these, you know, we get certified, but it doesn’t actually mean that we’re actually going to be qualified to be great teachers or great superintendents. And so one of the things that we miss is that reflective piece about what happened, and then what did we learn from it? And then how can we make better decisions in the future and making that part of our system? 

And so, you know, I look at your own, you know, Nine Principles, you know, your framework that you have about building the right culture and all those types of things. But it’s, really embedded in all that is a systems thinking approach by building your culture and then supporting your goals and getting there. 

And so for me, the podcast stemmed from wanting to be a resource for the field. If, in fact, that the national average for superintendents is about three years. And then if you’re a woman or a leader of color in leadership in the superintendency, it’s less than that. It’s about two years and sometimes 1.8 depending on who’s giving the data. 

And so I thought, well, what if we could create this resource for the field that would encourage leaders to come on the podcast and talk about a decision they made and then what they learned from it and then going through that very scripted after action review to say, “OK, so what got overlooked? What did you learn about relationships? What frustrated you? What could you have done differently,” which is different from what got overlooked sometimes because sometimes it’s a system and then sometimes what was your role in that system? 

And then always in the end ending with, “OK, so what was something that was good that came out of this?” Because you hope that in the future, when a similar scenario presents itself, you know what you did in the past and then it will inform better decisions, which then hopefully allows you to really do the good work that you were hired to do. 

Janet Pilcher: Yeah. You know, it’s that reflective practice, Peter. And, you know, sometimes we just don’t take that time, right? And I love what your podcast does. It kind of forces people to take that time and really answer those questions and think about it because that’s where we learn when we really reflect and look at what’s not working. Sometimes what’s working, but what’s not working. It’s when we really deeply understand what we’re doing and how to make those changes. 

Peter Stiepleman: So true. 

Janet Pilcher: You know, just, so what have you learned? You know, I mean, my gosh, it’s just a wealth, you’re a wealth of information and knowledge. 

Peter Stiepleman: [laughs] Well, I mean, it’s so, you know, we both have quite an affection for one of your coaches, DeDe Ashby, and DeDe was one of the first to join the podcast in my first season. And then she introduced me to some amazing people along the way. And I continued to get to meet and talk to them. And that’s what’s so interesting is they’re so incredibly reflective, so clearly they have been through a very similar protocol of trying to think about past practice, how it informs their current situation. And then, without dwelling on the current is then, how do you set some really meaningful and achievable goals? And so that’s what this is about. 

And so if someone were to go to my website and or go to the podcast, but on the website, you can do a search for topics that you might be interested in. Oh, you’re opening a new school or you’re closing or you’re considering closing a school or you’re going for a bond or a tax levy increase or you’re rolling out new curriculum. And, and what were some lessons that were learned so that maybe you could avoid those mistakes in the future? 

Janet Pilcher: Yeah, that’s great. That’s a great resource, Peter, because that’s going to, I mean, whatever is going to come up within a time, people are going to want to know how to answer that or what other people’s experiences have been. 

You know, as I think about it, I mean, you probably felt like this when you were a leader as well. And I’ve been, been fortunate in life. I had an opportunity to move into a leadership position pretty early in my 30s. And, you know, once you’re down that leadership path, you’re always down that path. Like you, you’re never out. laughs] You’re in it. 

Peter Stiepleman: [laughs] And I think of the Godfather movie, right? Every time you try to get out, they pull you back in. 

Janet Pilcher: You’re down the road. But I still, you know, after three decades of being in leadership positions, I mean, I’m always humbled by, by every day of leading because you’re always learning. I mean, there’s, as soon as you think you know everything there is to know, there’s something that occurs that you know that you really don’t. And it’s just a very to me humbling profession. And it’s a great passion of mine.

You know, but as you think about what you’ve learned, what you’ve heard over the years, you know, what advice do you have for leaders as they’re guiding their districts, as they’re going through the changes that continuously occur? You know, what, what do you offer them? 

Peter Stiepleman: Oh, that’s so great. So one of the things I was thinking about is just sort of like, what are some sort of the themes that I keep hearing? And one is making decisions with the people most impacted is often one that leaders, sometimes they fall victim to that impulse to make a quick decision. They see something happening. They want to, they want to impact it positively, and they start moving in a direction without first really engaging those who are most impacted. 

An example from one of my podcast conversations was Jerry Almendarez in Santa Ana, California, who he was working with the community, the business community and his principals. And so inside and outside the system to work on the portrait of a graduate: What do we expect children to be able to do when they leave our school district and how can we position them to be successful in the future? 

And as he was sort of unveiling this to all of the principals, a principal who had the courage and boy, Jerry had the the ability and the vulnerable, willing to be vulnerable to realize, “oh, my God, I made a mistake here,” which is, he, the principal raised their hand and said, “you know, I look around the room, and we’ve not engaged one single student about their future.” 

And so I think about this idea of like you really have to engage those who are most impacted. Shouldn’t we talk to the students about what they see about their futures and the kind of coursework that they might want to do? So when I think about that to really respond to your question is I believe in this idea of collective aspiration, sort of like being clear on what we want to create together. 

And then secondly, what are those nested patterns? How will we be together? And so I think it really aligns nicely with the work that you do as Studer in terms of everything from communication at all levels, right? But also really building that culture and then focusing on that engagement, particularly with those who are most impacted, your employees. 

And then lastly is serving as that lead learner, A, being willing to admit when you make a mistake, but also to apply these habits of systems thinking. And so I guess my advice would be to really create that culture. 

I once, two years ago, I went to a Studer session at AASA, and is it Pat showed this, Pat Greco, I think is her name, right? Is, I mean, a tremendous leader and had this image of this arrow and inside the arrow was embedded other pieces. And it always stuck with me because I like to use the metaphor of a murmuration of starlings. 

You know, when you see them over a field, they’re all flying together and they all are moving in the same direction, all supporting each other. And so when you have these questions that leaders are facing about the federal government getting involved in in terms of reducing federal funding. OK, so how do I find ways to leverage these existing partnerships that I have, as well as harvesting the collective wisdom of the people within my own system who can really move us in the right direction or all the noise around book bans, you know, and saying, OK, then you just take a step back because it really is noise. And how do I reclaim the narrative about the amazing things that are happening for children within my school district? 

So I think that would be my advice is sort of looking at that collective aspiration, those nested patterns, the being that lead learner. And then how do I take all of that to really support my system in a meaningful way? 

Janet Pilcher: Yeah, I love that, Peter. You know, I think it’s as I’m thinking of it, there are external factors and internal factors. We can’t control the external ones. We have to. 

Peter Stiepleman: Oh, totally. 

Janet Pilcher: But we can control the internal, you know, so our energy spends exactly what you’re talking about. We spend our energy on what we can control. And it really is with the people who are doing that that legwork each and every day, that heavy lifting each and every day, and as leaders really supporting them as part of our team. 

You know, just just love what you said, because so critical in terms of, it seems so big, Peter. But in essence, it can, we don’t have to, it doesn’t have to be that big. We can really simplify and make it smaller in terms of what we can accomplish. 

Peter Stiepleman: Janet, you would have been so disappointed to me in my first year as superintendent when I unveiled eight organizational goals. 

Janet Pilcher: [laughs] Oh gosh.

Peter Stiepleman: And, you know, when you’re focused on eight things, you’re focus on nothing. Right. And so it’s terrible, terrible. 

Janet Pilcher: Yeah.

Peter Stiepleman: So you are so right. They’re, you know, really simplify and you’ll start to see some amazing things. But oh, my God, those eight goals, and I watched the eyes of all the 150 administrators assembled in a room and going, “and we’re going to focus on kindergarten readiness. And we’re going to focus on the third grade reading. We’re going to focus on the transitions from middle school and high school. We’re going to focus on–” they’re like, “oh, my God.” [laughs] 

Janet Pilcher: Like I can’t even comprehend. 

Peter Stiepleman: Right. Exactly. “Will he stop talking? No, it looks like he’s still going.” [laughs] 

Janet Pilcher: Yeah. And one of the one of our core values as part of our standards of excellence is make the complex simple, right? That’s kind of, and not that we always do because sometimes we can over complicate, but every time when we do, we just talk about let’s make the complex simple. Let’s simplify, simplify, simplify. And so, so difficult to do, but important. 

Peter Stiepleman: Well, but your people have done it. I mean, I got to meet Sergio Mendoza right from California. I got to meet Jen Lowry in North Dakota or South Dakota. Oh-oh, she’s going to be mad at me. I know, I know. 

Janet Pilcher: [laughs]

Peter Stiepleman: Dakotas, I think I just lost all my Dakota followers. And Matt Robbins, I mean, all these in Kentucky. I mean, really the influence that you’ve had and obviously it’s not a commercial for Studer as much as obviously people are listening. And so I just want to reinforce, just each of them have really embedded that message about in terms of simplifying. So just kudos to you.

Janet Pilcher: They have. They have. They’ve done phenomenal, phenomenal work. You know, I always say we get to work with the best leaders in the country. And that’s a, that’s a privilege and an opportunity for us. 

So as we close today, I’m going to just kind of take us out a little bit. 

Peter Stiepleman: OK. 

Janet Pilcher: So we’re looking, you know, we’re looking at some major changes that are occurring. And we’re, we’re looking at some of those external factors, but really just the changes that are naturally occurring within K-12 education. I work in higher ed, too, and those changes are occurring as fast, very fast. 

And so when we look 10 years out, our profession is going to be somewhat the same, but different. They’re going to be different factors, Peter. You know, so what, what do you think? When you think about our profession 10 years out, what do you think about? And then how do we prepare ourselves from your expertise? What are your thoughts there? 

Peter Stiepleman: Oh, yeah. So this is as my mentor would say, a juicy question. And I think that, so when DeDe and I were talking a couple of years ago, I presented this scenario to her of you have a reporter waiting outside your door and they’re just so excited to talk to you because you did it. And so what was it that you did and how did you get there? And it’s that kind of scenario- building that really helps one kind of think about where you’re going. 

And so, in sort of recent conversation I’ve been having, or just in terms of the readings that all of us are doing around AI and things like that, I do think the next 10 years you’re going to see examples of not replacing the incredible humans who have the professionalism and the expertise to teach children because each child in their developmental stage and they need to be valued and honored and that can only be done in that human to human connection. 

At the same time, I also see where you’re going to have almost classroom aides like a Siri within your, within your own classroom that says, “Siri, can you work with Jamie and give the maybe 10 examples of the work that we’re doing in algebra and make them increasingly more difficult? And I want you to document where there’s a point of confusion. And then in about 15 minutes, I want you to tell me that that time has passed so that I can work one on one with Jamie.” Like, I actually think those things are going to happen as, as assistants in the classroom. And my advice is to embrace that and try to figure out how to leverage that and do that because it’s going to happen. 

I think also we’re going to see examples for children that are going to knock down the walls of schools even more. So we learned a lot with virtual learning. And I think, and we learned a lot what not to do with virtual learning. But I think you’re going to see examples of Carnegie units maybe melting away or at least becoming less of a focus on whether, on being able to demonstrate that children have learned shouldn’t be about how many minutes you sat in a seat, but rather the demonstration of knowledge and learning. 

And so I do think that children for a period of their day will even be able to put on a VR headset or some type of augmented reality and attend classes in another school in town or even another state or even another country where they’re going to have access to just great minds and other classmates who have similar interests. And I think we need to embrace that as well. 

So I guess my advice is to lean into that discomfort and be willing to maybe try some things and then be that lead learner. Learn what works and what doesn’t work. 

Janet Pilcher: Yeah, it’s so interesting. I, I was listening to or reading a news article that was talking about the college degrees, Peter, and it does connect to the AI. So they’re they were talking about, so interesting. They were talking about computer science is not necessarily as much of a valuable degree as it used to be because the technology is changing so much. 

Peter Stiepleman: Yeah, you know how to code? Great. But I can ask chat GPT to actually write my codes for me. 

Janet Pilcher: Yeah. And it’s not that, you know, it’s those things changing. But the, but the degrees that really have help individuals have human relationships are becoming more important because it’s going to be the relationship part that’s connected to the AI. I just thought that was fascinating. 

Peter Stiepleman: I totally agree with it. I mean, think about the people that you connect with or the people that most impact your life and it’s that emotional impact, that emotional intelligence that they bring, that ability to empathize. 

I was talking with I’ll have to send you his name because I don’t want to misstate it. He’s an expert in this work that and said, “you know, people know how to empathize and they’ll do it, but you have to actually engage them to tell them.” I went, how would this person feel about this in this situation? People don’t naturally empathize. They have to be animated to do it. And I think so many of us who excel in this work do that as a sort of a national function of leadership. We really do consider the how other people are going to be impacted by our decisions. 

And so I agree. I agree that that, I do hope to see sort of a renaissance in that work, not just the technical, but the ability to connect human to human. 

Janet Pilcher: That’s right. Well, Peter, thank you so much. It’s been so enjoyable having the conversation and good luck with the, with your podcast and thanks for sharing your expertise and for sharing your time with us. 

Peter Stiepleman: Janet, I’m so grateful that you gave me some time and really, truly, it’s so nice to see you again. 

Janet Pilcher: Take care. 

Conclusion

[Outro music plays in the background.]

Janet Pilcher: It was a pleasure to meet Peter at this past AASA conference. As I mentioned, we share many professional connections. Discovering and engaging with like-minded leaders is something I deeply value. And I’m grateful he agreed to be my guest today. 

Thank you, Peter, for creating a platform for leaders to share their experiences and insights so others can learn from them. Your podcast is exceptionally valuable to the field. 

Before we wrap up today, I urge you to follow Peter’s podcast. There’s a direct link in the show notes. You can also visit his website, imperfectleader.com, to learn more about him and his book titled An Imperfect Leader, Leadership in (After) Action

One truth about leadership remains constant–the need to recalibrate. When that need arises, let’s commit to doing like Peter said, making decisions with the people closest to the work, engaging those who are most impacted whenever possible. That’s what Peter taught us today and continues to teach many. It was a great pleasure and was so excited to engage with Peter on the show today. Thank you, Peter. 

And as always, I thank you for tuning in to this episode of the Accelerate Your Performance podcast. I look forward to seeing you next week as we continue to work together to achieve organizational excellence. 

Have a great week, everyone. 

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Featured Guest

Dr. Peter Stiepleman
Leadership Coach, Podcaster, Author, & Retired Superintendent 

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