The Power of Stability: Why Retaining School Leaders Will Shape the Future of Education

Mike Montoya: 00:00:00 Welcome to The Stronger Podcast. Each week we have honest conversation with education and social impact leaders about their leadership and career journeys. We talk about their origins, inflection points, and the work that they're doing today. The conversations are honest, human, and practical. If you're here for real stories, and real takeaways, you're in the right place. Let's jump in and let's get stronger together. Before we dive into today's conversation, I want to give a quick shout out to podcastmatter.com. Their mission is to help impact driven voices get the visibility they deserve. If you want to share your message with the world, check out their website in the show notes.

Mike Montoya: 00:00:55 Good afternoon. I am super excited to be here. Sorry it took me a minute to turn my head on about this. We're recording a few bridge episodes as we head into 2026. So that while I take a little break with my family, there's a lot—there's some information flowing from our company and our work, right, and into into our audience this week. And so appreciate everybody taking the time to kind of have a sidebar with me. I call it that. And and to think about like, hey, what's ahead in 2026? I was kind of doing some work and planning with my team about the upcoming hiring season.

Mike Montoya: 00:01:40 I'm going to talk about that a little bit and maybe reflect on a few other things. This will be a short one, but I think but in general, I wanted to share about like what's exciting in 2026 in terms of school leadership and what we're seeing across the marketplace and some predictions right now. Of course, you know, let me be clear about this—data on hiring and employment in the education sector is sparse. It's sporadic. It's certainly not consolidated. It's not clear at all.

Mike Montoya: 00:02:15 We know that there is a teacher shortage. We know that there's a school leadership challenge in the sense that like school leaders do not stay in their jobs the same way that they did 10 years ago and that the experience and depth of school leadership is highly variable across the entire marketplace and K through 12 public education. Right? So let's just be clear, right? We're in a place of inflection—an inflection point where things are not the same as they used to be like say pre-2025.

Mike Montoya: 00:02:45 And I would say like they're not great data sets to give us a sense of like what's ahead; each individual school system, charter school network, or public school district is experiencing this in a different way. Some of these systems have really great pipelines for leaders and do a lot of work to develop really great leaders for the future leadership of their school sites, and other ones have weaker pipelines and weaker systems for leadership and development and readiness. And the teacher pathway—the pathway from classroom educator up through kind of school leadership or system leadership—is not a clear flat direct line. It is varied and it moves around a lot.

Mike Montoya: 00:03:30 There's lots of pathways to becoming a successful school leader or assistant leader, but most of them are anchored in great teaching experiences in the classrooms and having great development schools of ed and then great first, second, third year principal leadership. So, some of the data shows that like when a school teacher has a great first couple years in a school that's high functioning with a school leader or principal that's coaching and teaching them and supporting them, then they have kind of bones or the chops to get into their next leadership role.

Mike Montoya: 00:04:15 And when they lack those really strong experiences, then they have a different pathway; they're maybe not as prepared to be great leaders because they didn't have great developmental experiences in their early years as an educator. And so, like the data on this stuff is kind of weak and it's not well documented like how to develop great school leaders. There are some actual schools of thought on this and the schools of education certainly have an angle on this—Relay of course does—and other big institutions that produce great teacher leaders, but there's not like a national consensus about like what makes a great school leader and how do you get them there.

Mike Montoya: 00:05:00 Some of the best work though about like the importance of principals came out of a study from the Wallace Foundation a couple years ago and about how principals affect students in schools. Basically it's like the school principals have a pronounced positive effect on the school that they lead and the critical feature here is that we need consistency and cohesion inside of a school system. And it's important that we work kind of collectively to make sure that we're providing for systems that support school leaders to do their jobs well and for them to be in those roles doing a good job for multiple years at a time because transitions and turnover really just cause chaos.

Mike Montoya: 00:05:45 This is not just about school leaders, but like any time you have a leadership transition in any kind of organization, there's a challenge about like, hey, where is this going and what's the vision and how are we going to move forward as a unit together. The school is sometimes thought about as the unit of change. Sometimes the classroom is the unit of change in terms of like how do you improve things, but at Stronger Consulting we think about the school as a unit of change because that's like a critical feature. And we hire lots of school leaders for lots of organizations.

Mike Montoya: 00:06:20 I think we've done about 90 plus school or instructional leadership roles over the last three or four years and that gives us a little bit of experience about what kinds of folks are in the marketplace and which ones are really prepared. I think for each of those jobs that we probably have talked to several hundred individuals and so if you multiply that out it's several thousand, tens of thousands of people that we've talked to over the last four or five years on school leadership work. And so our sense of this is like not comprehensive but it gives us a richer experience than say just a single school site might have.

Mike Montoya: 00:07:00 And so I think our team is well suited to be supportive of school organizations to think through what a school leadership pipeline needs to look like. How do you get and attract really high-quality school leaders into your school system? How do you keep them and retain them? Because once you hire school leaders, like of course you need to support them and help them be successful. You can't expect that they can do it all their own and sometimes like that expectation is just completely unrealistic that the school leader can run the school and and build a team and hire and coach and train 20-something plus adults inside of a school.

Mike Montoya: 00:07:40 If the school has 300 or 400 kids, there's 20 or 30 adults running around trying to make the whole thing work. And one school leader is not able to do all the systematic things that are necessary to make this successful and to be great, we might call it school community leaders—people that engage families and children and parents and grandparents and extended caregivers all over the place. School leaders are expected to hold all of this together in some way, but it's sort of an unrealistic expectation to do that without a bunch of systems and processes in place.

Mike Montoya: 00:08:20 Sometimes the school systems have that stuff built and other times they don't. And I think it's one of the things that we do well is helping people think through how to do those systematic development of retention components all geared at making sure you have a great school leader that sticks around and is able to lead the school for multiple years. And I reflect on some of the folks that we placed historically, and one young man could be—I know you're out there somewhere—he came from Tennessee back to Los Angeles for a role and stayed in a leadership role at a school system in 2016, 17, 18 all the way through 24 roughly.

Mike Montoya: 00:09:05 So five or six years in that school system and he built a really incredible school community like he's a founding school principal I think and helped that school develop into a really thriving exciting place to be. And then over time that transitioned out of his leadership as he moved on. But great—I got to call him because I'd love to hear him tell his story about that work. You know, there's gems out there; I call them just really caring, brilliant educators that have both the knowledge and skills and the drive and intuition to do this work.

Mike Montoya: 00:09:45 I think it is a craft to be a school leader; it's one of the most passionate rich jobs that can exist. And one of our other clients, Julian Juman, would say like I only want people who love the job to take that job. People who love being a school leader, but sometimes people see it as a stepping stone to something else. And sometimes people just do it to check a box or they kind of fall into it, but like the people who really love being a school leader do such incredible work and they can be found in the marketplace and they can be hired and trained and supported.

Mike Montoya: 00:10:25 If you're able to do that as an organization, bring those folks in, it's an incredible experience. And then you have this amazing school community that develops and literally children are growing up in these spaces as they go through their whole childhood in these school systems. If they have two or three school leaders that make a critical difference in their life that's the magic, and that's what I think we can aspire to be. Not only are they achieving things academically but like the school community is rich and robust and has created a space that's safe for them to be the children that they are to turn into young adults that are passionate and caring.

Mike Montoya: 00:11:05 A lot of this is done because of the construct of the school unit. So, it's super interesting work. It's one of the my favorite things about the work that Stronger Consulting does is hire school leaders. And we want consistency and continuity for kids and their families. And we want to continue to encourage like the deep and rich focus of resources on academic programs and interventions that support children's diverse learning experiences. There's like so much that like the kids in the norm—that works for them.

Mike Montoya: 00:11:40 And then there's a lot of stuff that's on the edges of kids both in terms of special needs but also kids that have higher capacities—intellectual curiosities that need to be developed as well. All of this stuff is possible when you have a school system that cares about all kids, not just the norm in the middle. And so we encourage again the thoughtful resource allocation to both kids that need more on all sides of the spectrum, but also to ensure that no kid is left behind. I hate to use that phrase, but it's such an interesting thing that the data and the utilization of data to see how kids are doing academically on high stakes tests at least points to the fact that we're not doing a great job with some kids.

Mike Montoya: 00:12:20 And some kids we're doing great jobs with and I think in many cases those kids would learn regardless of what we did with them. Sort of like stay out of the way would be supportive enough. But for some kids, they need more. And if you're a parent or if you have children or have been around them, you know that not every kid functions the same and needs the same stuff. And so it's really amazing when you can get school leaders that develop school systems that are responsive to all kids.

Mike Montoya: 00:13:00 So that's my take looking forward to the 2026 hiring season. My prediction is that there will be some turnover in the school leadership ranks this year, but perhaps a little bit less than in the 2021-22 era. But the school leader job has changed and I think it's become a little bit harder in some ways; it's more demanding to get kids to show up on a regular basis. There's some of that enrollment issues going on across the country in most systems. Like kids just don't come to school as consistently as they used to. There's a bunch of chronic absentee data out there.

Mike Montoya: 00:13:45 And so the onus is on us as adults to make these spaces inviting and welcoming and high quality so that kids want to be there and that their families see it as highly valuable. But we think there'll be some turnover in the school leadership ranks this year. But again, the volume will be super high. Maybe I think we're one year away from when people have been in a job for three or four years and they're like, "Oh, I'm really ready to move." Right? So, we're kind of in that state of like maybe they've been there two or three years now. Next year will be their fourth.

Mike Montoya: 00:14:25 So, I think we'll have like a little bit of a medium-sized season this year in terms of hiring, but that there will be an expansion of hiring in 2027 because there'll be more turnover as people kind of hit their three or four year mark and they'll be looking to make some moves and changes. So, we don't know what's going to happen in the hiring season. It's a little bit of a funny job market that there are fewer jobs right now. People are kind of hunkered down and sort of riding the wave of the federal government's kind of messiness.

Mike Montoya: 00:15:00 I think there's opportunities here for us to double down on resources for investments for leaders and teachers that are in our school systems right now and sort of ride the wave of having consistency right now. Let's capitalize on it and do our best we can with the folks that we have and continue to develop the future leaders as a result of our time with them now. So, I'm looking forward to spending the season with our clients and new clients and you know, Stronger Consulting is always available for conversations around school leadership development.

Mike Montoya: 00:15:25 This year we're helping design two or three leadership academies around school leaders in particular. Those are emerging right now, and so that's super exciting. We're also building two or three pipelines for new school leaders, kind of innovative school options in certain states. That's happening in Connecticut and in Nevada, maybe New York as well. And so there's some bright spots happening across the country, right? Bringing more options to kids, higher quality options, alternative options to sort of some of the traditional stuff that's out there.

Mike Montoya: 00:15:45 And so we're huge champions of this work and we're excited to work with our various partners on this work and look forward to seeing the results in time as these new leaders get into spots of leadership. So thanks for your followership. Very much looking forward to hearing from you. Always feel free to reach out mike@strongerconsulting.com. You can find our newsletter. You can find all of these podcasts on strongerconsulting.com. And we wish everyone a great start to the new year. All right, we'll see you soon. Bye-bye.

Mike Montoya: 00:16:05 Thanks for joining us and tuning in today. To find out about other podcasts that matter, visit podcastsmatter.org. Thanks for listening to the Stronger Podcast. If this conversation inspired you, we invite you to follow the show and share it with someone who's on a journey to become a happier and healthier version of themselves. Links and resources a