98 episodes

Hello and welcome to An Imperfect Leader: The Superintendents and Leadership Podcast, a series where leaders look back at decisions they made and ask themselves:

* What happened?
* What got overlooked?
* What did you learn about relationships or what new relationships were formed?
* What frustrated you?
* What could you have done differently?
* And in the end, what was something good that came out of the experience – because it is through our mistakes where our greatest learning takes place.

I'm Peter Stiepleman. I'm your host AND I'm an imperfect leader. I spent more than 20 years teaching and leading, first in the Oakland Public Schools in Oakland, CA and then in the Midwest – Missouri, to be exact – where I was a teacher, a principal, an assistant superintendent and the superintendent of the 4th largest school district in a state of more than 500 districts.

I am constantly striving to learn from my experiences and from the experiences of other leaders. The aim of this podcast is to lift the learning and lift the imperfect leaders up. That way, when you hear the term imperfect, you’ll see strength, strength from the candor needed to recognize imperfection as a real advantage.

an imperfect leader, TLI, peter stiepleman, Dr. Peter Stiepleman, imperfect leaders, school culture, education, culture, school, positive school culture, principal, superintendent, aspiring superintendent, new superintendent, experienced superintendent, leadership, district leadership, school leadership, school leadership thoughts, inspiration, strategic planning, leadership development, human-centered leadership, collective aspiration, nested patterns, leaders’ learning work, educators, superintendent pipeline, Model for Human Centered School Transformation, transformation, podcast

An Imperfect Leader: The Superintendents and Leadership Podcast Peter Stiepleman

    • Education
    • 5.0 • 78 Ratings

Hello and welcome to An Imperfect Leader: The Superintendents and Leadership Podcast, a series where leaders look back at decisions they made and ask themselves:

* What happened?
* What got overlooked?
* What did you learn about relationships or what new relationships were formed?
* What frustrated you?
* What could you have done differently?
* And in the end, what was something good that came out of the experience – because it is through our mistakes where our greatest learning takes place.

I'm Peter Stiepleman. I'm your host AND I'm an imperfect leader. I spent more than 20 years teaching and leading, first in the Oakland Public Schools in Oakland, CA and then in the Midwest – Missouri, to be exact – where I was a teacher, a principal, an assistant superintendent and the superintendent of the 4th largest school district in a state of more than 500 districts.

I am constantly striving to learn from my experiences and from the experiences of other leaders. The aim of this podcast is to lift the learning and lift the imperfect leaders up. That way, when you hear the term imperfect, you’ll see strength, strength from the candor needed to recognize imperfection as a real advantage.

an imperfect leader, TLI, peter stiepleman, Dr. Peter Stiepleman, imperfect leaders, school culture, education, culture, school, positive school culture, principal, superintendent, aspiring superintendent, new superintendent, experienced superintendent, leadership, district leadership, school leadership, school leadership thoughts, inspiration, strategic planning, leadership development, human-centered leadership, collective aspiration, nested patterns, leaders’ learning work, educators, superintendent pipeline, Model for Human Centered School Transformation, transformation, podcast

    Andrew Dolloff Turned Mascot Mayhem into a Culture of Courage

    Andrew Dolloff Turned Mascot Mayhem into a Culture of Courage

    Hello Imperfect Leaders!
     It's summer!! And for leaders, that means reflection. And it means planning for the coming year. It is for that reason that this week's episode is an encore episode specifically picked with your upcoming year in mind. 
    As Labor Day approaches, Season 3 will kick off. And I am so excited about THAT because  Jamie Almanzán from The Equity Collaborative will be joining me as a cohost and commentator. It's going to be great! So, sit back and enjoy this encore presentation of An Imperfect Leader: The Superintendents and Leadership Podcast.
    INTRO: Choosing a name for a public building is a challenging process. With schools, a new name often includes the choosing of a mascot as well. Renaming a school or changing a mascot is often even more difficult. Community members will allege you're erasing history. I was a superintendent presiding over the renaming of Robert E. Lee Elementary School in Missouri! Most recently, I served on a renaming committee in the Seattle area. The committee process was well conceived and thoughtfully carried out by the district's current Superintendent, Amii Thompson. She made sure to make decisions with those most impacted, in this case, the Suquamish Tribe. 
    Now, imagine if you were the principal and your school board decided on a Thursday night to remove an offensive mascot effective immediately. My guest is Dr. Andrew Dolloff, superintendent of Yarmouth Schools in Yarmouth, Maine. His After Action Review is about exactly that! Thanks for tuning in.
     
    Bio: Dr. Andrew Dolloff has been the superintendent of schools in Yarmouth, Maine since 2014.  He is a 35-year veteran of Maine public schools, having begun his career as a chemistry teacher and basketball coach in central Maine before moving into school administration in Greater Portland in 1996. Andrew has served as a superintendent, assistant superintendent, high school principal, high school assistant principal, and athletic administrator. For nearly 10 years, he has served a community that is deeply personal to him as his grandfather graduated from Yarmouth High School. I have no doubt that leading in a hometown district must have made it even more meaningful when he was named Maine’s Superintendent of the Year in 2021.

     -----
    An Imperfect Leader is sponsored by Yondr. 
    Schools around the world are seeing the damaging effects of phones on student engagement, social development, and mental health.
    Yondr has developed a unique product and program to allow schools to become phone-free, from arrival to dismissal.
    Learn why 1 Million Students use Yondr every day.
    MINIMIZE DISTRACTIONS. MAXIMIZE LEARNING POTENTIAL.
    Go to overyondr.com to learn more.
     
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    At the end of every interview we have for teacher candidates, we say, “What questions do you have for us?” And they always ask, “What kind of support can I expect?” And we always say, “Don't worry, we'll give you a mentor.”
    But it's not real mentorship. I mean, it's support with the difficult kid, or the field trip form, or the grade card. But it isn't coaching. 
    That's where partners like EdConnective step in. Because they provide real coaching, observations and feedback with practice. EdConnective ensures that every student thrives by facilitating exceptional educator growth. If you're looking for support for your people, for your leaders, for science of reading efforts, for recruitment and retention initiatives, check out EdConnective.com.

    ------
    Imperfect Leaders! Are you facing challenges filling open Speech-Language Pathologist positions within your district? Empat Speech understands the critical need for qualified professionals in your schools. The recognize that communication lies at the heart of academic success. Don't let open positions hinder your students' progress. Partner with Empat Speech today and ensure every child in your district has access ot the speech therapy they deserve.

    -------

    • 41 min
    Matt Hornbeck Redefines Public Education

    Matt Hornbeck Redefines Public Education

     Hello Imperfect Leaders!
     It's summer!! And for leaders, that means reflection. And it means planning for the coming year. It is for that reason that this week's episode is an encore episode specifically picked with your upcoming year in mind. 
    As Labor Day approaches, Season 3 will kick off. And I am so excited about THAT because  Jamie Almanzán from The Equity Collaborative will be joining me as a cohost and commentator. It's going to be great! So, sit back and enjoy this encore presentation of An Imperfect Leader: The Superintendents and Leadership Podcast.
    INTRO: This week, Matt Hornbeck is my guest. He is the principal of Hampstead Hill Academy in Baltimore, Maryland. In our conversation, we talk about the importance of relationships in schools and we talk about restorative practices (he describes the process of fixing what has been broken so so well).
     
    In his After Action Review, we talk about the early years of leadership and what can be learned when a leader focuses more on what they want as opposed to documenting what they don’t want. The topic is staff attendance. Thanks for tuning in!
    BIO: Matt Hornbeck is an established leader in Baltimore, Maryland. Before becoming a principal at Hampstead Hill Academy, a Baltimore City charter school, he was an educational consultant with large urban districts on resource allocation and principal training. He holds a master’s degree in Educational Administration as well as a law degree.  

     -----
    An Imperfect Leader is sponsored by Yondr. 
    Schools around the world are seeing the damaging effects of phones on student engagement, social development, and mental health.
    Yondr has developed a unique product and program to allow schools to become phone-free, from arrival to dismissal.
    Learn why 1 Million Students use Yondr every day.
    MINIMIZE DISTRACTIONS. MAXIMIZE LEARNING POTENTIAL.
    Go to overyondr.com to learn more.
     
    ------
    At the end of every interview we have for teacher candidates, we say, “What questions do you have for us?” And they always ask, “What kind of support can I expect?” And we always say, “Don't worry, we'll give you a mentor.”
    But it's not real mentorship. I mean, it's support with the difficult kid, or the field trip form, or the grade card. But it isn't coaching. 
    That's where partners like EdConnective step in. Because they provide real coaching, observations and feedback with practice. EdConnective ensures that every student thrives by facilitating exceptional educator growth. If you're looking for support for your people, for your leaders, for science of reading efforts, for recruitment and retention initiatives, check out EdConnective.com.

    ------
    Imperfect Leaders! Are you facing challenges filling open Speech-Language Pathologist positions within your district? Empat Speech understands the critical need for qualified professionals in your schools. The recognize that communication lies at the heart of academic success. Don't let open positions hinder your students' progress. Partner with Empat Speech today and ensure every child in your district has access ot the speech therapy they deserve.

    --------
    An Imperfect Leader: Leadership in (After) Action is supported by ILAA, LLC, a firm dedicated to supporting aspiring, new, and established leaders. For more information, please find them at www.human-centeredleaders.com.
    Music for An Imperfect Leader was written and arranged by Ian Varley.
    Sam Falbo created our artwork, a wood-print inspired daruma doll butterfly.

    • 33 min
    Dr. Avis Williams is Leading New Orleans Through Change

    Dr. Avis Williams is Leading New Orleans Through Change

     Hello Imperfect Leaders!
     It's summer!! And for leaders, that means reflection. And it means planning for the coming year. It is for that reason that this week's episode is an encore episode specifically picked with your upcoming year in mind. 
    As Labor Day approaches, Season 3 will kick off. And I am so excited about THAT because  Jamie Almanzán from The Equity Collaborative will be joining me as a cohost and commentator. It's going to be great! So, sit back and enjoy this encore presentation of An Imperfect Leader: The Superintendents and Leadership Podcast.
    Intro: Hello Imperfect Leaders! On August 29, 2005, Hurricane Katrina, a Category 3 hurricane with recorded wind speeds of 140 miles per hour devastated communities in Alabama, Mississippi, and Louisiana. I remember being a teacher in Missouri, and hearing reports of families heading north to find refuge all along the Mississippi River.
    Our school system welcomed families, and quickly learned of their very specific needs. The children had been through a great deal of trauma. What I didn’t know until now was that after Katrina, in 2014, the New Orleans Public Schools transitioned from a traditional school district to a 100% charter school district. The superintendent would be hired by a school board, and it would be their responsibility to oversee and authorize each charter school (working with each charter school’s own school boards). What a task!
    My guest this week describes that important work. Dr. Avis Williams is the New Orleans superintendent. She reminds us that “When you’re bringing people together around an issue, there is a difference between buy in and commitment (you’ll hear her say, “if people can buy in, they can be bought out.”). Listen for it. 
    She also describes the creation of a Joyful Educator Collaborative where she convenes teachers to learn more about what is going well as well as areas for continued growth. Thanks for tuning in!
     
    Bio: Dr. Avis Williams is the superintendent of schools for the NOLA Public Schools in New Orleans, Louisiana. Prior to her historic appointment to lead the Nola Public Schools, Dr. Williams served as superintendent of Historic Selma City Schools in Selma, AL for five years. 
    An award-winning educator and sought-after speaker, she is a native of Salisbury, NC.  A product of poverty, Dr. Williams dreamed of being a teacher from an early age.  As a first generation 4-year college student, she followed the path of her older siblings and joined the Army right after high school. While in the Army, she was stationed at Fort Jackson, SC, Yongsan, Korea, and Redstone Arsenal in Huntsville, AL. 
    Further Info: Dr. Williams is a leader, a learner, and an author. She is the author of Welcome to Chase Shadows and of professional articles like Leading with Joy as a Prerequisite to Better Outcomes. Additionally, she has a professional book (co-authored with Bren Elliott) coming out soon.
     -----
    An Imperfect Leader is sponsored by Yondr. 
    Schools around the world are seeing the damaging effects of phones on student engagement, social development, and mental health.
    Yondr has developed a unique product and program to allow schools to become phone-free, from arrival to dismissal.
    Learn why 1 Million Students use Yondr every day.
    MINIMIZE DISTRACTIONS. MAXIMIZE LEARNING POTENTIAL.
    Go to overyondr.com to learn more.
     
    ------
    At the end of every interview we have for teacher candidates, we say, “What questions do you have for us?” And they always ask, “What kind of support can I expect?” And we always say, “Don't worry, we'll give you a mentor.”
    But it's not real mentorship. I mean, it's support with the difficult kid, or the field trip form, or the grade card. But it isn't coaching. 
    That's where partners like EdConnective step in. Because they provide real coaching, observations and feedback with practice. EdConnective ensures that every student

    • 36 min
    All Aboard the Energy Bus: Dr. Jim Van Allan's Road Trip to School Leadership!

    All Aboard the Energy Bus: Dr. Jim Van Allan's Road Trip to School Leadership!

    INTRO: Hop on the Energy Bus for our latest podcast episode! This week, we're thrilled to have Dr. Jim Van Allan, a nationally recognized speaker and co-author of The Energy Bus for Schools, take the wheel. Jim shares his expertise on school leadership, student engagement, and the power of positivity in education.
    In this episode, discover how Jim's journey and dynamic approach can transform a school's culture. Whether you're an educator, administrator, or just passionate about positive change, this conversation is packed with valuable insights and practical tips, include:
    Part 1: We dive into the themes of the book, especially in the post-pandemic world. 
     
     
    Part 2: In our "Imperfect Leadership in After Action" segment, Jim shares a humorous, yet insightful story about a speaking engagement mix-up in Wyoming. 🤦‍♂️ His anecdote highlights the importance of flexibility and problem-solving in leadership.
    Don't miss out on this enlightening and entertaining ride with Dr. Jim Van Allan! Tune in and get ready to fuel your school leadership with enthusiasm and positivity.
     
    BIO: Dr. Jim Van Allan is the co-author of The Energy Bus for Schools (a companion to The Energy Bus, a best seller his co-author, Jon Gordon wrote, having sold over 3 million copies). In addition to being the President of the Energy Bus for Schools program, Jim is a Professor of Communication Studies at Keiser University. He holds a Ph.D. in Education Leadership where he studied the impact of The Energy Bus for Schools curriculum on a model school.

    ------
    An Imperfect Leader is sponsored by Yondr. 
    Schools around the world are seeing the damaging effects of phones on student engagement, social development, and mental health.
    Yondr has developed a unique product and program to allow schools to become phone-free, from arrival to dismissal.
    Learn why 1 Million Students use Yondr every day.
    MINIMIZE DISTRACTIONS. MAXIMIZE LEARNING POTENTIAL.
    Go to overyondr.com to learn more.
     
    ------
    At the end of every interview we have for teacher candidates, we say, “What questions do you have for us?” And they always ask, “What kind of support can I expect?” And we always say, “Don't worry, we'll give you a mentor.”
    But it's not real mentorship. I mean, it's support with the difficult kid, or the field trip form, or the grade card. But it isn't coaching. 
    That's where partners like EdConnective step in. Because they provide real coaching, observations and feedback with practice. EdConnective ensures that every student thrives by facilitating exceptional educator growth. If you're looking for support for your people, for your leaders, for science of reading efforts, for recruitment and retention initiatives, check out EdConnective.com.

    ------
    Imperfect Leaders! Are you facing challenges filling open Speech-Language Pathologist positions within your district? Empat Speech understands the critical need for qualified professionals in your schools. The recognize that communication lies at the heart of academic success. Don't let open positions hinder your students' progress. Partner with Empat Speech today and ensure every child in your district has access ot the speech therapy they deserve.

    --------
    Music for An Imperfect Leader was written and arranged by Ian Varley.
    Sam Falbo created our artwork, a wood-print inspired daruma doll butterfly.
    -------

    My book, An Imperfect Leader: Leadership in (After) Action is available at Amazon.com or peterstiepleman.com.

    • 34 min
    Redefining School Leadership: A Conversation with Dr. Peter Dillon

    Redefining School Leadership: A Conversation with Dr. Peter Dillon

    INTRO: Welcome to today's episode of An Imperfect Leader, where we sit down with Dr. Peter Dillon, a superintendent in Western Massachusetts. Peter shares his experiences working in a rural region serving, at one time, two school districts and the lessons he learned along the way.
     
    In this episode, he shares insights on leading multiple districts, the challenges and rewards of serving small communities, and the process of redesigning what it means to be a high school student in a post-COVID world. Don't miss this conversation about harvesting collective wisdom, overcoming budget crises, and fostering student voice and engagement. Dr. Peter Dillon shares his story and lessons learned, embodying the spirit of an imperfect leader.
     
    BIO: Dr. Peter Dillon is the superintendent of schools for the Berkshire Hills Regional School District—serving the towns of Stockbridge, West Stockbridge and Great Barrington, Mass. At one point, he also served, simultaneously, as superintendent of the Shaker Mountain School Union, which serves Richmond, Hancock and New Ashford. Previously, Peter was executive director of policy in the Office of Portfolio Planning at the New York City Department of Education, where he helped to create and sustain more than 150 new schools. He was the principal of the Heritage School in East Harlem and he taught in New York and in the Republic of the Marshall Islands as a Peace Corps volunteer.
     
    ------
    An Imperfect Leader is sponsored by Yondr. 
    Schools around the world are seeing the damaging effects of phones on student engagement, social development, and mental health.
    Yondr has developed a unique product and program to allow schools to become phone-free, from arrival to dismissal.
    Learn why 1 Million Students use Yondr every day.
    MINIMIZE DISTRACTIONS. MAXIMIZE LEARNING POTENTIAL.
    Go to overyondr.com to learn more.
     
    ------
    At the end of every interview we have for teacher candidates, we say, “What questions do you have for us?” And they always ask, “What kind of support can I expect?” And we always say, “Don't worry, we'll give you a mentor.”
    But it's not real mentorship. I mean, it's support with the difficult kid, or the field trip form, or the grade card. But it isn't coaching. 
    That's where partners like EdConnective step in. Because they provide real coaching, observations and feedback with practice. EdConnective ensures that every student thrives by facilitating exceptional educator growth. If you're looking for support for your people, for your leaders, for science of reading efforts, for recruitment and retention initiatives, check out EdConnective.com.

    ------
    Imperfect Leaders! Are you facing challenges filling open Speech-Language Pathologist positions within your district? Empat Speech understands the critical need for qualified professionals in your schools. The recognize that communication lies at the heart of academic success. Don't let open positions hinder your students' progress. Partner with Empat Speech today and ensure every child in your district has access ot the speech therapy they deserve.

    --------
    Music for An Imperfect Leader was written and arranged by Ian Varley.
    Sam Falbo created our artwork, a wood-print inspired daruma doll butterfly.
    -------

    My book, An Imperfect Leader: Leadership in (After) Action is available at Amazon.com or peterstiepleman.com.

    • 35 min
    Dr. Melvin Brown on Weighted Grades, Systemic Change, and Serving as a Lead Learner

    Dr. Melvin Brown on Weighted Grades, Systemic Change, and Serving as a Lead Learner

    INTRO: In my third year as a superintendent, the AVID classes at one of my high schools invited me to the school library at 7:30 in the morning. That is EARLY for high school students accustomed to starting school at almost 9 o’clock, so it had to be important. Over donuts and juice, it was the students who led an activity called Philosophical Chairs. The topic? Weighted grades. Our school district didn’t offer weighted grades and the students saw this as a distinct disadvantage. They were prepared for my argument to maintain the status quo. I reasoned, “Why would we need weighted grades? The research is really clear. If you complete an AP course, even with a C, you’re more likely to complete college.”
    In Philosophical Chairs, after each statement, participants can choose to move in proximity to the person making the statement. I didn’t sway anyone. A student then stated, “I hear the argument that completing an AP course shows me that I can handle a college course, and that it becomes more likely I will finish college, but I need to GET into college first, and I need to get a scholarship to pay for it, and a peer who takes a less rigorous course and gets an A gets accepted to college and gets a higher scholarship.”
    She was right (we verified this with our local University and they weren’t stripping weighted grades from transcripts). I was won over. I wish I could say that this change happened immediately. Getting 4 votes from the school board took some time, but we got there. My guest, Dr. Melvin Brown, shares his experience with a decision he made about weighted grades in Montgomery, Alabama. 
     
    In Part 1, Melvin Brown talks about the importance of reclaiming the narrative in Montgomery Public Schools. He talks about how enduring change will take time. He talks about recognizing the systems that exist, persist, and ways to RESIST. We discuss the ways external partners like EdConnective can support leadership development.  We talk about the goal of increasing opportunities like algebra at middle school and the systems thinking approach that will be necessary to do that.
     
    In Part 2, we talk about weighted grades, how AP courses and honors courses earned the same full point on a transcript, and the unintended consequences on a student’s future (scholarships and such). Dr. Brown lived the role of a lead learner.
     
    It’s a great episode. Also, this episode had one of my favorite lines ever! I laughed out loud when Dr. Brown described himself as a student. He said, “Summa Cum Laude? No, it was more like, thank you, Laude!” I edited out my outburst!
     
    BIO: Dr. Melvin Brown is the Superintendent of the Montgomery Public Schools in Montgomery, Alabama, a position he has held since 2022. Previous to that, he served as Superintendent of the Reynoldsburg City School District in Reynoldsburg, Ohio. And before that he served as a Superintendent in Residence and Visiting Professor at The Ohio State University. And before that, he held various leadership roles: as Deputy Superintendent, as Director of Human Resources, as an Associate Superintendent, and as both an elementary middle school principal.

    ------
    An Imperfect Leader is sponsored by Yondr. 
    Schools around the world are seeing the damaging effects of phones on student engagement, social development, and mental health.
    Yondr has developed a unique product and program to allow schools to become phone-free, from arrival to dismissal.
    Learn why 1 Million Students use Yondr every day.
    MINIMIZE DISTRACTIONS. MAXIMIZE LEARNING POTENTIAL.
    Go to overyondr.com to learn more.
     
    ------
    At the end of every interview we have for teacher candidates, we say, “What questions do you have for us?” And they always ask, “What kind of support can I expect?” And we always say, “Don't worry, we'll give you a mentor.”
    But it's not real mentorship. I mean, it's support with the difficult kid, or the field trip

    • 30 min

Customer Reviews

5.0 out of 5
78 Ratings

78 Ratings

Michele510 ,

Incentive to be better every day!

Peter and his podcast are an embodiment of true education and what it means to be a lifelong learner. Recognizing that we’re all imperfect, even many of our role models, serves as a great reminder of why it’s unnecessary to dwell on our mistakes or let them hold us back. Instead, Peter and his guests encourage you to embrace those lessons and use them as incentive to be just a little bit better every day. As a former teacher myself, I only wish I had found this show sooner!

Jc Nnz ,

The HBR Leadership Podcast for Educational Leaders

Dr. Stiepleman’s expertise and humanity come through in his interview style. He puts guests at ease and bonds with them to provide excellent practical advice for educational and systems-oriented leaders, and those aspiring to be.

He guides his guests to embrace imperfect leadership and the decisions that come out of it. With vulnerability as the basis, this podcast is kind of a coaching conversation, where the listeners get to eavesdrop for free.

I can say I have adopted ideas shared by his accomplished guests, and adjusted my practice based on the learned lessons of their experiences.

Premium content for free!

Thanks Dr. Stiepleman!

ListenerABCDE ,

We need more leaders to be vulnerable!

Great concept and interviews - we need more like this!

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