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.

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.

INTRO: As many of you know, I serve on the Board of Directors for Be the Change Volunteers. We build schools, teacher housing, and bathrooms all over the world (currently in Peru, Malawi, India, Rwanda, Puerto Rico, and Papua New Guinea). It’s an incredible experience – if you ever want to join a build, please let me know – and one thing we try to be mindful about is the return back home after a build. You’ve just seen a lot and experienced a lot, and there is a transition back to your regularly scheduled programming. When I was speaking with my guest today, she highlighted the importance of preparing employees for when they are relocated to another country.

Brenda Harrington is my guest. In Part 1, we talk about her book, Access Denied, which seeks to support the trailblazers in your organization, the one, and often the only one in a work space and the importance for peers to be aware of the cultural field they create, curate, and permit to persist.

In Part 2, we talk about an area of Brenda’s experience that many leaders will relate to: the need to move to a new community, sometimes in a new state (you’ll hear my initial confusion about the term global mobility). Brenda talks about the coaching needed before a leader changes locations and the call to companies to think about an employee’s success.

BIO: Brenda Harrington is the CEO and founder of Adaptive Leadership Strategies, a service business that offers coaching and consulting solutions to help companies develop and grow top talent. In addition to Brenda's work as a CEO, she is also the author of Access Denied.

INTRO: When I was a superintendent, we created a geometry and construction class. Kids would take geometry on A days and then apply those principles to building a tiny home on B days. And I loved asking a student who was out there working on the home in the dead of winter why it was important to be out there working when it was so cold outside. “Today, I’m cold. Tomorrow, someone will have this home and will no longer be cold.” I loved that response. Our kids were learning, geometry, home building, empathy, and compassion. We had another class where on A days kids learned algebra and on B days, they applied their learning to a small business, a t-shirt company, they were operating. Finding ways to build relevance and entrepreneurial opportunities. These weren’t my ideas. I just was smart enough to support the educators who came to me and pitched these classes. My guest today reminded me of the importance of reclaiming the narrative about public schools - how innovative they really are and how they support opportunities previously unheard of in traditional schools (an entrepreneurial hub for students, internships, real world experiences, early college for juniors and seniors to graduate high school with an Associate Degree, debt free). Please welcome Dr. Scott Menzel.

In Part 1, we talk about creating opportunities for kids and the importance of reclaiming the narrative when it comes to public education. Scott’s rallying cry is a simple one: Because Kids. He believes the misinformation and disinformation must be confronted because otherwise false narratives take root. In our conversation, I give the example of a State Representative in Missouri who continues to claim that children are allowed to identify as cats and use litter boxes at school. Scott responds with a strategy for leaders on how to reclaim the narrative.

In Part 2, Scott talks about a technology initiative, a three-year pilot, using VR technology to improve middle school and high school math achievement. He describes the difficult decision to pull the plug on the initiative and what he learned from that.

BIO: Scottsdale Unified School District welcomed Dr. Scott A. Menzel as Superintendent on July 1, 2020. Always looking to the future, Dr. Menzel’s approach to education is student-centered with a relentless commitment to excellence and opportunity for all. Having provided 18 years of leadership to school districts within the state of Michigan, Dr. Menzel became Scottsdale Unified School District’s 27th superintendent on July 1, 2020. In 2023, he was named Superintendent of the Year by Save Our Schools Arizona and in 2024 received ERDI's Resilient Leader Award.

INTRO: I almost called this episode: You’re the Villain in this Story because of the absolutely horrific story my guest shared with me in this week’s episode. Holy cow, you’re going to want to listen to this entire episode!

Sometimes as school leaders, you are forced to make difficult decisions. Whether or not to non-renew an employee can be really difficult. Whether to close a teaching section, which will increase class sizes, is an agonizing decision. My guest this week made the gut-wrenching decision to cancel his school district’s football season. He did it for all the right reasons. He did it while considering the short-term, long-term, and unintended consequences of the decision. He did it with empathy and compassion.

Please welcome my guest, Dr. Richard Labbe.

In Part 1, he discusses the importance of coaching for new teachers though the EdConnective. He then touches on the decision to cancel the football season.

In Part 2, he returns to the football decision because there were many moving parts to the decision. His After Action Review is an incredible resource for our field. I’m grateful for Dr. Labbe’s willingness to revisit a very difficult career decision.

INTRO: When I first became a superintendent, I learned about Positive Coaching. Positive Coaching is a framework for winning kids with sport by building relationships with children first and foremost. The way I saw it, Positive Coaching emphasized the aspect of doing something together and learning how to be a team. It wasn’t about winning at all costs. I loved it. My guest today will talk about something that still makes her cringe a decade after it happened. I could totally relate.

One of my first acts as a superintendent was to gather all the coaches from the 6 middle schools and 4 high schools. I told them we were going to be positive coaches, that we weren’t going to want to win so badly that we were going to damage kids. I always tell leaders that you must get a beat on the system before you go out and make pronouncements. I should have followed my own advice. I am certain I insulted so many of the incredible adults who were already positive coaches. What I needed in that moment - heck, what I needed well before that moment - was a leadership coach.

Today, my guest, Dr. Natalie Nichols will talk about the value of a leadership coach (in her case leveraging EdConnective to help leaders support literacy instruction in their schools) and then she’ll tell us her cringe moment when she unilaterally chose to institute a dress code at her high school.

• In Part 1, Dr. Nichols talks systems thinking. If her district is going to have an impact on reading achievement, she knows that her leaders are going to need the very best training to support their teachers. She identified that the approach to teaching reading is a BIG topic and can be controversial. It is with the understanding of building technical skills while also attending to the affective side of change that she chose to partner with EdConnective to provide personal coaches for her leaders.

• In Part 2, Natalie tells me about an early decision in leadership when she made the unilateral decision to Institute a dress code at the high school she was leading. She talks about what she learned from this experience and how it has helped inform the steps she takes as a district leader.

BIO:

Dr. Natalie Nichols is the Senior Chief of Schools and Innovation in Round Rock, Texas. With over 20 years of experience in education, Dr. Nichols spent a decade serving Round Rock ISD in two major leadership roles as an Area Superintendent and principal of Round Rock High School, the District’s largest campus. Dr. Nichols has been an associate principal, an assistant principal, and an instructional specialist. She has also supported public school districts across the nation through the use of educational technology.

In this week’s An Imperfect Leader: The Superintendents and Leadership Podcast, we dive into another authentic story of someone navigating the complexities of leadership. I'm your host, Peter Stiepleman, and today, we have the honor of welcoming a remarkable leader, Merle Horowitz.

Today, we’ll explore Merle's journey through a lens of empathy, resilience, and the pursuit of progress - or in her wise words: we’re going to empathize, sympathize, and energize. With a focus on the profound impact of mentors and the challenges of cyberbullying in education, Merle shares her insights drawn from years of experience. From her groundbreaking research on the legal implications of digital communication to her tenure as a superintendent, Merle's journey is a testament to the transformative power of leadership in education. In Part 2, Merle walks us through her experience of leading a major facility change where academic learning spaces would get the same attention as football fields.

It's a great episode. Thanks for tuning in!

BIO: Dr. Merle Horowitz has been a teacher and a district leader, retiring as Superintendent in Marple Newtown, Pennsylvania after serving four decades.

As superintendent, she led district-wide renovation projects to bring the district’s schools up-to-date with security and technology improvements, all of which served as a catalyst to the transformation of the district’s academic environment and staff and student morale. In fact, this led to schools in her district being awarded the Governor’s Award for Excellence in recognition of student achievement.

Recognized as an administrator for demonstrating a commitment to school administration as a profession, to public education, and to one’s colleagues – for that Merle was named the recipient of the 2014 PASA Award for Leadership in Public Education. In 2014, she co-published an article on cyberbullying, which turned into a book: Cyberbullying in Social Media within Educational Institutions.

INTRO: Before listening to this episode, I want to make sure that you know that this episode deals with trauma. If you have experienced trauma in your past, you might want to find the right time to listen to this episode. And remember, if you or someone you know needs the suicide or crisis lifeline, you can dial 988 from any phone.

For me, the experiences my guest describes in this episode were a reminder of leading a school district during the pandemic. I can still remember it like it was yesterday. The year was turning from 2019 to 2020. I was a superintendent and I started hearing about a virus appearing in Seattle and New York. I wrote a note in my journal that we should plan to give an update on the emerging coronavirus at the April board meeting. In mid-March, however, I had a meeting with the Director of the local Health Department. It was abundantly clear the presentation would need to be way earlier than April. I would be explaining why the virus would be closing the district down.

I remember responding to questions from community members. They wanted to know how this year was different from past years when there were high cases of the flu. In all other years, I thought, we were not directed to stay in our homes by every level of national, state, and local government. In all other years, we were not tuning in to the news or talking with neighbors who had been impacted in some way by this global pandemic. In all other years, we hadn’t felt such tremendous loss. And I can remember hoping for a return to normal routines. Everyone was hoping for that! Unfortunately, like school districts all across the globe, each decision caused more and more grief.

My guest, an author and former army veteran and trainer, talks about how to talk with adults who have experienced trauma. School leaders, all leaders, are not often trained to handle their own distress, nor are they necessarily skilled at recognizing the trauma of others. Dan Joseph is a terrific guest because he talks about the things to look for, the things to notice (like people being hypervigilant, for example). In the second part, he describes a time when a soldier was dealing with mental health during lockdowns. People were struggling with their own traumas and didn’t have the bandwidth to help this individual. The directions were to keep it quiet and stick with the mission.

It’s a fantastic episode.

BIO: Dan Joseph is an Army veteran and author of Backpack to Rucksack: Insight Into Leadership and Resilience From Military Experts. When I’ve read parts of his book, reviewed combatpsych.com tools, and listened to him on The Power of Our Story, I was struck by some of the similarities we look for when it comes to leadership (in the military and in education), including the ability to look back and see what we can learn from our experiences.

NOTE: Here is a link to a Harvard Business Review article I mention on self awareness.