Education
S05E15 - Balancing Two Districts and One Mission: A Journey Through Leadership and Change | Dr. Matthew Montgomery, Superintendent
In this episode of Build Momentum for Education, Dr. Matthew Montgomery shares his unique experience as the superintendent of two school districts. He discusses the challenges and rewards of leading m...
S05E15 - Balancing Two Districts and One Mission: A Journey Through Leadership and Change | Dr. Matthew Montgomery, Superintendent
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Interactive Transcript
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Hello and welcome to Build Momentum for Education, a podcast where we explore thought leadership
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and education.
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I'm Sarah Williams and the founder of SWPR Group, an agency that supports public relations,
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communication strategies, and thought leadership support for school districts, education
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companies, and nonprofit organizations.
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And I'm Chebos, Chancellor and Ivy Tech Community College in India.
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This season we explore a particularly unique, perspective in K-12 thought leadership,
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humanizing the role of the superintendent.
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Throughout the many conversations we continue to have with superintendents, a clear theme
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has emerged about the need to bring more humanity into the role of the superintendent's
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seat.
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In this special series, we interview current and former superintendents and researchers
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to pursue the core question.
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How can we better see superintendents as real people navigating complex challenges to
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provide the best possible education for K-12 students?
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We dig deeper into how this important work can help build community, invite collaboration,
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and increase widespread engagement.
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We can't wait to get started, so let's dive in.
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So welcome to Build Momentum for Education and we're thrilled to have Dr. Matthew McCumry,
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Superintendent of Lake Forest Community High School District 115 and Lake Forest Elementary
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School District 67.
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And so our podcast here, will you please tell us a little bit about your career as a superintendent
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where you have lead districts?
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And we've talked a lot of superintendents, but we have not talked to anyone that is a
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superintendent of two school districts.
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And we know that one is tough, two is unreal.
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And so we want to hear all about that and how you became the leader of two districts.
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Well, thank you, you're very kind.
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I appreciate you having me with you today and I'm confident that you've talked to amazing
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colleagues across the country because there are incredible leaders that are doing amazing
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work and I am proud to learn from them each and every day.
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So this is my third and fourth superintendent, see respectfully, which means that I was
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born and raised in Ohio and I led two districts in Ohio, one rural district, very small at an
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incredibly early point in my career.
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And then one suburban district that was a little bigger and had more resources than the
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rural environment.
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And then when I moved to the Chicago land area, this was the first time that I ever attempted
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to be a part of two districts, Chad, to your point simultaneously.
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It is not a very common scenario for a superintendent to have two.
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I don't give me too much credit though because they've been doing it for a long time before
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me.
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I just joined the process with them.
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Actually, we just celebrated 20 years of shared services, which means that the district,
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I oversee an elementary district, which is Lake Forest District 67, as well as a high school,
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which is Lake Forest Community High School.
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There is another elementary feeder, Lake Bluff District 65, that has their seven board member
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and individual superintendent, her name is Dr. Lisa Leoli, doing incredible work and happy
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to call her a friend and a colleague.
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So both elementary's feed into the high school of which I'm a part of.
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So I have two boards of seven.
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There are four collective bargaining agreements, two and two, two for each district.
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Everything is separate except for about 35 to 40 shared service employees that help support
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both districts.
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So think of human resources, business department, facilities, teaching and learning, as well
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as then the superintendent themselves or myself.
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It is by far the most challenging leadership opportunity I've been given or afforded.
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And now that it's year four, it feels great.
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And I don't want it any other way.
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Actually, one of the options or one of the things I was charged with when I started was
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should the district's remained shared services or not.
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That was one of my goals in my first contract.
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And I reaffirmed what many people have before me determined, which is a mutually beneficial
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and symbiotic relationship, terms of economy and scale, as well as maximizing continuity
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between elementaries and the high school.
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And it acts, it doesn't act as a unit district.
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And that's what I led in Ohio, which are pre K 12 districts.
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And there are pre K 12 districts in Illinois.
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So even though it is not a unit district, it's symbols or mimics one in certain spaces.
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And then it's uniquely different in others in terms of there's all of the budgets.
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It's just double everything in terms of how the state identifies us and everything that
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goes with the work.
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This is my 12th year as finished, not my 12th year of superintendent, which sounds incredible
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and acknowledging that each year of the superintendent is equivalent of aging in dog years.
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So I'm still kicking and happy to be here.
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But I can't, gosh, could I tell myself stories if I knew what I knew now then because leadership
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continues to evolve and change.
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Yeah, I'm sure that's so impressive.
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I still think it's pretty impressive that you're running to districts.
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I know you're not giving yourself credit, but wow, two boards, that's impressive.
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Equal, I'm really lucky actually.
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And if I could just take a moment, some people struggle.
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I had a five member board in Ohio and both of those districts.
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And here I have two of seven.
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And I continued to have my bucket filled by non agenda student focused, community focused
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board members who come together with the help of a Lake Forest caucus and also a caucus
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like process in Lake Bluff where they screen the community screens, public service officials.
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And what you find is this not for profit HR firm within the community that is bringing
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the best of the best forward.
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And I will tell you that I am very, very lucky to have 14 board members who care about
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kids and want to do right for the community.
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That's incredible.
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Well, well done.
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So you clearly find this job rewarding.
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I'm work here.
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So we'd love to hear throughout your career what you found to be the most rewarding aspects
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of school leadership.
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So when I started as a teacher, I was a high school science teacher and I always wanted
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to know what was happening in the principal's office or what happens when they would close
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the door.
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And that always intrigued me.
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And I thought, gosh, maybe I could make a bigger impact in terms of change in making
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young people's experiences better if I went to the next spot.
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So when I got to the principal's office, that I was curious about what was happening
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in the superintendent's office.
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And now I make the joke that when I'm in my office, if anybody walks in and closes the
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door, I'm like, oh, please don't.
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Like I've had my fill of what happens, but it is the most rewarding experience I've ever
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had in my life when you are making changes and you're always playing for the long game.
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So oftentimes the work you're doing does not come to fruition for one, two, three, four
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years in advance.
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So I really like seeing projects from ideation to ribbon cutting to see that unfold.
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Hopefully I'm still in the district.
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I want to be here for a long time.
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And I have this sense of urgency to complete what I start, but it's in those quiet moments,
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years after when you've started something that you have to almost take the beat and say,
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wow, the team did it or things that we thought weren't possible weren't.
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And that continual and cycle of improvement is something that I love to work on.
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The meeting I just left, we're thinking about a project that will not come or could not
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come to the earliest would be two years out for the conversation we just had.
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That's exciting to always be forward thinking in this role.
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Well, I think this next question is kind of why we started to have conversations with
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superintendents across the country.
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And a 2023 Rand study found that superintendents have one of the most stressful jobs in America.
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And so we could ask all of the folks who join us in this series, their thoughts on these findings.
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Do you see these as bringing true and how have you been able to cope with the stress that the role
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brings?
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So when you hear these studies, I don't know if I feel reaffirmed that yes, things are different
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or that things are stressful at times.
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I also think that many leaders that matriculate to the superintendents or CEOs standpoint
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in public sector or private thrive on stress to some degree.
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In fact, we are experts in stress management, the ones that are surviving and thriving.
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So it's common to say that it's one of the most stressful jobs because leadership is stressful.
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And I often say that in retirement, I hope to sell ice cream on a beach with three flavors.
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And if you don't like the three, there's another shop that you can go see and make people happy
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while they're on vacation because this is a job that requires ultimately you have to say no
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sometimes. As much as you want to say yes, you are telling no and there's only so many knows you
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can divvy out in a year to make sure that you can continue to sustain to do great work for kids.
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I will tell you that the level of stress changed pre-pandemic during the pandemic and post-pandemic.
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And what I found most intriguing was that the stress level did not come down post-pandemic.
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It stated the level and or increased. And I think it increased because of the polar,
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this is my hypothesis, this is not been tested. It's increased because of the polarization that we're
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seeing in society within the states and beyond. And it is, I remind people that we have to listen
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to understand, rather listen to respond. And we are in the midst of an area where critical conversations
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had through dueling keyboards and I'm not talking about a piano situation. We are trying to get the
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next clever thing or a point on and not really hearing each other. So I am looking for in my own
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leadership and then the conversations I have with the community is we want to talk about what's
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in the gray. We want to see and value the opposing viewpoints and come together because it is the
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only way in my humble opinion to get forward movement. And if you have that mindset, I think it shifts
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where I sometimes surprise people by who I meet with, which is always, I have two German shepherds
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at home and whenever I talk to them, they do this, they turn their head. When somebody says,
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why would you meet with somebody, I do the same thing because you have to have in-person
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conversations with people about difficult topics if you want to be a leader who can move a
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community forward with their wishes, not my wishes, the community's wishes. And then if I can,
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I think you added an element, Chadda, in that question about how do you cope with stress? If I
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may transition to segment, sometimes not well. And I think that that took me several years to
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realize it was okay to say when I wasn't okay. And thankfully with a very supportive family that
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often gets neglected and an incredible spouse who tells me when I'm off-kilter, it is that balance
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of how well you're eating, how much are you exercising? Are you giving yourself to have peaceful
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moments? Are you disengaging in a strategic way so you can fully engage when you need to?
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And in a job that's exceptionally stressful, you need an army of people around you to say when
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they think that you are at or over capacity. And then my experience is apologize profusely when
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you make a mistake. And those people who you're closest with, whether I'm speaking to myself,
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the people I'm closest with, whether it's my cabinet or my family are often the ones that get
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abused the most when I am dysregulated. And apology, apologizing and trying to do better is the
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most effective way that I've found to continue to try to manage my own workload.
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Yeah, and you touched on this a little bit earlier, Dr. Montgomery, about how the scrutiny of the
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role has changed over the past several years. Can you elaborate on that a little bit more?
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I think the scrutiny is coming. Maybe it was always there, Sarah. I think the mediums in which
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people can offer their scrutiny is more in the moment and omnipresent of individuals who can
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freely weigh in on any action that they have differing or you could say or they could agree with you.
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But it's often the ones you're hearing from the ones that have differing viewpoints. That onslaught of
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feedback is difficult to process in the role. It's always been difficult, but especially difficult
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now. And having other people around you say maybe you shouldn't read that or if you read it,
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here's how I'm going to support you during these time of strife because it does when an
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individual's moral compass is aligned with the community and you're doing what you believe
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is right for the students that you're serving. And then there's this disconnect.
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There's a lot of reflection and self analysis of did I actually make the right decision and my
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moving in the right direction and you need to you need the levels of support because it is
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non-stop on Facebook groups, X, Instagram, and then you just fill in whatever ones I'm not saying,
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whether it be Snap or usually the younger students are using some of the different modalities.
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Then you have emails and phone calls and face-to-face impact as well.
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Believing into the criticism is my biggest strategy as opposed to leaning away. And I find that
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if someone is elevated or upset, I get curious because maybe there are things that there are
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likely things we could be doing differently. Maybe there's things that we could do differently
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in in a more student or family-focused manner. And I think if you're curious, it helps from a
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leader's standpoint that you move from defensive to curious. And maybe it's because I'm
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blessed with several teenagers in my house and they are growing and changing in the most beautiful
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way. But they are, they feel quite freely to offer feedback to their dad about how he can be
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better. And as much as I don't want to listen, that 9 times out of 10, they're right or they're
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onto something. So if you're a leader and you translate to putting walls up in front of people
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who have opposing viewpoints, perhaps that is not the way to actually have progression.
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There's a ton to unpack in that answer alone. And so we could spend I think days on that subject.
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So we'd love to talk to you further about that. But I'm going to ask you the question about your
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role. As you see this, do you think that your experiences are similar to or are the same as most
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of the other superintendents you encounter in your state and across the country? Do you think that
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folks who are having a similar experience to you or do you think yours is different?
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I do not think mine is different at all. I think that when I was in a rural district of 1100
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with no resources, and I would talk to colleagues who are running districts of 50,000, 75,000 or more,
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and now I'm in a two small districts, right? And I talked to superintendents in a rural setting,
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suburban or urban. It doesn't take very long into the conversations to see the common threads were
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all experiencing real time. And I think that's because we're all engaging in leadership roles.
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So you're meant for likely to have similarities in the experiences and differences. Sure,
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cabinets look different, teens look different. You may have resources. You may not. You may have more
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economic diversity or diversity of races or pick whatever the breakdown of the individual community.
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The threads are that leadership is the most rewarding and challenging role that people can
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experience at times. And it is a privilege to be given this responsibility that doesn't mean
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it's easy. But if it was easy, I think more people would want to do it.
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Absolutely. We're in a bit of a crisis, a leadership crisis for superintendents across the
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country and finding more of them. A friend just posted an article about that. The P.J.'s article?
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Yes, this thread. I was like, that's well done. He's that brings that really well, the neat.
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P.J. summarized it nicely. And I think that when you think of the future of this organization,
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and when I say, I say public education is the organization I'm talking about, we need more
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superintendents or people who want to go to superintendents. We need more principles. We need
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more teachers. So you can widen this scope beyond the superintendent role. But one of my most
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rewarding experiences and responsibilities is to create opportunities for people lower in the
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organization who want to aspire to be a superintendent and then helping them go forth and become a
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superintendent or become a principal. We need to be encouraging people to take on these roles.
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At the same time to P.J.'s point, we need to have a community that understands that you need
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great people leading organizations. And how we treat our leaders matters and increases the
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likelihood when one leader leaves, you are going to find another great leader to follow. And I will
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say that leaders, exceptionally effective ones, but I would widen this to everywhere, can be
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selective and where they are choosing to lead. And the articles in which come up on a Google search
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of a community directly impact the desire of new leaders to join that community and put their
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name in the hat. So while you think it doesn't matter when you shoot off that angry email or
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publish that angry post, know that it could have an impact. And if you're trying to instill change,
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maybe that's what you're after. But I really think that communities want great leaders supporting
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their kids. So those little interactions often translate into a longevity of leadership that you
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will be attracting as a community. Yeah, actually on that note, I have another question for you about
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the work we've been following the work you've been doing, particularly with the bond that you just
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successfully achieved last year. It was last year, right? 23. 23. Okay. So we'll
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Okay, we're curious about your strategy for bringing people together to help see your vision
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for the district, both districts like bonds, or even better to collaboratively build that vision
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together with your community. Tell us about that.
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This season of build momentum for education is all about the superintendency. We will spend time
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digging into the challenges you face running complex school systems, navigating political boards,
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divisive communities, and often vocal adversaries. But you continue to lead with grace and resilience.
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We are honored to recognize your humanity in this work. We know that your challenges are real.
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Tackling issues such as effective communication strategy that can galvanize communities to support
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what really matters the students. Through our many conversations with school leaders,
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we consistently hear districts struggle with enrollment declines and increasing competition
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from virtual and charter schools, navigating complex bond referendums and rallying community support,
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effectively communicating the district's story and resource constraints and limited staff and budget.
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SWPR Group specializes in confronting all of these communication hurdles with tailored strategic
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communication planning and strategic thought leadership support. We have worked with countless
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districts across the country to elevate their story and build community. Contact SWPR Group today
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at Sarah at SWPR-group.com to learn more.
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So can I expand a little bit farther out from a referendum and tell you just what our strategy is
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in terms of outreach to a community? Absolutely. Because I think it translates. And I would just
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like to put an aspect on your very kind that you say my vision and my successful passage.
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I want to say that it's a community's successful passage, our vision, and I played a small part in
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that. And I'm proud that I did. But I want to make sure that people know that one person cannot
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undertake these initiatives. It has to be a collective hole. And really as a leader, you are a
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conduit for an incredible amount of stakeholder voices that you need to try to find some cohesiveness
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and then be responsible for helping lead them in that direction that they have defined.
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The referendum itself is no different than any other strategy, which is interesting because we've
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talked about this a lot about the level of communication we offered with the community at the
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referendum is something that we have maintained beyond it. So connecting through, and this is a
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simple Sarah as board presidents and myself meeting people at a coffee shop four times a year.
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This is creating with the help of the team a superintendent advisory council with
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applications for community members to sit and help be listening and thought partner with me on
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decisions. This could be involving community members and important hiring of principles or directors.
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It's me shadowing students and having exit interviews for eighth graders leaving the 67 district
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or seniors leaving the 115. It's a capital project advisory committee where we had experts in
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the community come together and apply to be a resource for our architecture and engineering
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firm as well as our construction firm. It's bringing people in. So when I talk about previously
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about the idea of creating barriers, it's actually the opposite. You need to go out into the community
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and engage their thinking so you can represent them well. And I think the greatest example
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even bigger than the referendum is when we pulled together hundreds of people, maybe that's I'm
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going to say 150 people to create a portrait of a learner for district 67 district 65 and district
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115 with the help of my fellow superintendent, Dr. Leoli who I talked about and having 21 board
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members coming together. And then once a portrait was created with the community, then we created
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three separate strategic plans. Dr. Leoli did a five year for 65 and our team did one for 67
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and 115 and we had 50 people in each subgroup come together for that. Then we created metric
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documents for those strategic plans about how we were going to know that we're actually making progress.
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Then we created board goals and all of this now is aligned. The board goals even have a dashboard
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at the high school. I would have you look at it because I'm proud of the work that the team has done.
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There's a dashboard online of how the board goals are being implemented. So when I think about
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I'll reach whether it's a referendum or a strategic plan, meet people where they are and be willing
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to be receptive of critical feedback knowing that you're not selling ice cream. If you were,
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there's many more flavors than three and there's no beach. There is a lake forest peak by the way.
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It's lovely, but that's not where I'm working every day. Sorry, I made it to you. It is to do it well,
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it has to be ingrained into the fabric of the culture. And that takes longevity and leadership
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and stability within the boards to be able to do transformational work. So when you go back to
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the RAN study and you every time you turn over a leader or a board, the community is susceptible
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to this idea of initiative fatigue where faculty say we're done. We don't feel like we have a
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voice. We are not a part of the process. And what's the next gal or guy going to bring forward
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that they're going to make their mark? It is not about me as a leader. It's about how I supported
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the community while I was leading. Yeah, I love that advice too for other districts.
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Thanks for sharing that. I'm curious. One of the reasons we wanted to host this podcast series
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came about after we interviewed many leaders, superintendents for a book we're working on in defense
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of the superintendency. Throughout these conversations, we continue to hear how there's such a need to
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eliminate the humanity of superintendents. What do you think about that? Do you think it's important
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for us to see superintendents as real people who are navigating complex challenges to support
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our students? What are your thoughts? Can you say that differently for me to make sure I understand it?
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So you heard that there is a desire to remove the human experience from a superintendents?
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No, that superintendents. No, that's not what we're saying. It's not a big sort of hearing.
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We heard that superintendents often feel like people think they're robots that they're just
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doing a job and it's transactional and there's not really a lot of human element or human understanding.
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And one of the things that these people think might help improve the relationships between
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communities and superintendents and families and students is understanding that these are human
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beings and they're here to serve you but illuminating humanity of these superintendents could help.
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So that gives me a little bit. Thank you for being explaining it for me. There's a little bit of
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visceral response because early in my tenure, I was very comfortable in those two schools of
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thought. Some superintendents believe they should live and work in the community in which they're
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serving and others believe that you should have separation. And there's not that's not right or
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wrong. I'm going to tell you that I have always fallen into the lib with the communities by kids
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go to the school district and we are fully immersed. I was much more comfortable showing the
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human side of me pre-pandemic versus post-pandemic. And I think it speaks to the onslaught of attacks
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and also the fear some of my superintendents and I will speak myself included have had to have
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extra protection at different times during leadership because of whatever we were going through.
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So there's less willingness from me to show is much exposure into my family as there once was.
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At the same time, we are immersed in the community and very much a part of the community
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and proud to say that that's a reality. But I think there's more of a guarded nature that I take
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as my four children are going through the school districts and we're outside of activities. I'm
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just more I try to be more insulated. So is that not being human? I don't know. Is that protecting my
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own humanity and longevity? Maybe. How am I striking the balance is what I would ask myself. And
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talking about my family through them seeing me out and about whether to dance recital or track
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sectional where they see us as humans. And I think these communities appreciate the fact that
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I am going through parenthood with them in their schools. And we have brought in things that I'm
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struggling with at home. I'm bringing in authors and we're doing book studies to have conversations
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because I've come to realize that maybe we aren't supporting our families as much as we think we are.
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And as much as we're trying to support the kids, we have them for six hours and 18 hours their
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parent and guardians responsibility. And do they do they have the answers? Do they have the support
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they need? I'm supposed to be an educational expert and I'm telling you sometimes I'm immersed
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for children and I'm like, I think I better just go back to work. I don't know what I'm doing.
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And I think that authenticity as a dad saying we need to keep reading books. We need to keep
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having conversations about how we support our young people to make sure we are mentally fit
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as adults to support our students with everything they're facing. So that is the way I've tried to
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thread the needle of I'm a human doing this under this tremendous responsibility while still
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making clear lines of separation to make sure that we can still be a family unit and I can be a
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human outside of this job that sometimes is 24-7 not all the time just sometimes.
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Yeah. Thank you. Well, throughout this series, we've really enjoyed our conversations with
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superintendents. We were fans before. We appreciated superintendents, but I think we've really grown
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to I think a deeper understanding of who you are and what the position holds and some of the struggles
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and really great parts of the job are. So as being a supporter of the K-12 educators and the
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system as community members, parents, how can we better support our district leaders?
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I think assuming this is simple, assume positive intent. If we had a mindset of assuming positive
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intent, whether the school is calling the families or the families in community or calling the
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school or thinking about what we're going to post about each other, if we could assume positive
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intent, I think that that would be the best support that we can give each other. And this is still
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the job for me. And I will tell you that last week I was in classrooms, shadowing a student,
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and I still feel most alive when I am serving and supporting young people who are going to go out
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and do amazing things. So as hard as this job is, as hard as it, and I'm not winding when I say that,
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so some days it's just hard. The research now says it's hard. So I think as it gets hard,
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because the job forces you to be away from kids in the leadership role, because you're essentially
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you're running a business. People don't like to say that, but you're running a business,
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pushing yourself back into the classroom with the students you're serving,
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for finds a great deal of grounding to assume positive intent as a leader and ask for it from
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others. That's great. And I would love to know more about your shadowing of students. That sounds
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like a pretty cool. How often do you do that? So I do it once a year for both districts. And I
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would pick usually seventh or eighth year in then a junior. And I just follow them along for
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their classes, usually half a day, because they don't want to be with me more than that. And then I
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couple that with the exit interviews with the students subgroups, small subgroups of eighth
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graders leaving the elementary district and high school, high schoolers leaving the high school
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to try to get that student feedback. And then we're adding students to the board experience. One
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thing that one of our assistant soups and high school principals brought forward, not my idea,
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exceptionally probably did it though. As a leader, it's always wonderful to lead into great ideas.
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She helped orchestrate an experience for the students where the high school student leadership
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team students came together. And we had board represented from all three districts, the two,
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which I'm leader in the other elementary. And they were stationed at tables. And we had students
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rotate through with the board. And the board had questions for them about the student experience.
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And it allowed our boards of education to see real time the impact of our decisions as adults.
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And to get what the students were thinking about for future work. So I can't overemphasize
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the importance of student voice and decision making, because as much as adults, myself included,
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claim we have it figured out, we could always benefit from new and fresh perspectives. And we're
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supposed to be here for the students. So getting their voice at the table is paramount to success.
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So the folks that follow this podcast and listen to us, where can they learn more about you and
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connect with you directly? So there's multiple ways. If you want to find more about solely
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Lake Forest and all the great work that's happening there with the team and the community, I would urge
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you to go to the Lake Forest webpage. And you can get access to both the elements just
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freaking the high school on the main page. And then the channel I'm using most frequently is
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LinkedIn right now. So I would encourage you to, if you're interested, just message me on LinkedIn.
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And I will be happy to have further discussions. And I'm posting things that I'm finding a particular
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interest. Last week, I had the incredible opportunity to be on Stanford's campus and Google headquarters
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in Mountain View to learn from researchers how they are viewing the artificial intelligence state
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of the union kind of ideas. So as I'm coming up with experiences that I think are particularly
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helpful as a leader, I try to share them through LinkedIn. And I'm always looking for great ideas.
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So keep them coming because again, don't have it all figured out.
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This has been such a pleasure. Thank you so much Dr. Montgomery. We appreciate your time.
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Thank you both. And I hope you have, it was great visiting with you. I'm glad if you have any
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further questions or anything else, we're happy to help. Thanks for tuning into the Build Momentum
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for Education Podcast. If you enjoyed listening today, we would love to hear your feedback.
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And we'd be grateful if you could leave us a review. This helps us to share these powerful stories
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with even more people. If you like what you heard, we'd be honored if you could share this episode
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with someone in your network. We look forward to seeing you next time on Build Momentum for Education.
Topics Covered
Build Momentum for Education
K-12 thought leadership
superintendent role
education leadership
stress management in education
community engagement in schools
shared services in education
school district leadership
superintendent interviews
humanizing education leadership
collaboration in education
navigating challenges in education
support for school districts
public relations in education
education communication strategies