the slow work that's filling Kentucky's superintendent seats

This work puts you in a lot of rooms.

Budget meetings.

Legislative sessions.

Planning calls that run thirty minutes over.

And sometimes, if you're lucky, a room with a backdrop, a ring light, and a group of people who are exactly where they're supposed to be, even if they don't fully know it yet.

I didn't know Owens Saylor before he started building Kentucky Leadership Rising as part of one of our favorite partners, the Kentucky Association of School Superintendents. But the first time we talked, his enthusiasm for what he was creating was impossible to miss. He wasn't building a program. He was building something with purpose, for the right reasons, with the right people, in a way that actually aligned with something real.

When he asked me to come photograph the December cohort session and snap headshots of the aspiring supers, I said yes without hesitating.

I spent that day taking headshots for every single person in the room. Then I got to sit down with a handful of them, Jim Detwiler, Sarah Hatton, Monica Ballard, and Tiffany Hicks, for a short interview. Nothing formal. Just a few minutes of conversation while the room settled around us.

Click HERE to check out the interviews and testimonials from KLR alum on this curated playlist.

One by one, I kept thinking the same thing: these people are ready. They're not here for a certificate. They're here because they're called to this work, and someone finally built a room that takes that calling seriously.

I took a selfie on the way out after their group photo, me in the foreground, the whole cohort lined up behind me, and I drove home more attached to this program than I had any right to be.

Over the past year, I've been watching those people get the job.

Across Kentucky, between 15 and 20 districts have open superintendent positions each year. Over the past four years, that's nearly 60-80 openings across a state with 171 districts. Most of those seats get filled the same way they always have: a posting goes up, a search committee forms, and whoever rises to the top of the pile gets the keys.

That's not a pipeline. That's a waiting game.

Kentucky Leadership Rising is a leadership development initiative within the Kentucky Association of School Superintendents, designed to do something different. Not just develop aspiring leaders, but develop the right ones, in the right way, for the right reasons. The program runs from October through May. It holds around 30 participants at a time. It costs $1,000.

There is a competing program on the market now at nearly three times that price. KLR doesn't compete on price or packaging. It competes on proof.

Over the past year, KLR graduates have been stepping into superintendent chairs across Kentucky. Rex Booth at Trigg County. Nick Brooks at Wolfe County. Jessica Addison at Todd County. Jason Steffen at Ludlow Independent. Robert Braden at Taylor County. July 1 transition dates are being set. The KASS directory is updating in real time.

Now in its fourth cohort, KLR is producing what Kentucky's education landscape actually needs: leaders who were ready before they ever sat in the chair.

We helped build the infrastructure behind this program, and watching this harvest arrive has been one of the most quietly meaningful things I've experienced in this work.

Here's what I believe it comes down to.

quality 1: it starts with service, not status

Walk into a KLR cohort session, and you will not find people chasing a title. You will find people asking hard questions about whether they're actually ready and whether this is truly what they're called to do.

Monica Ballard put it plainly in her interview: she joined to change the way students are educated. Not to run a district. To change something for kids. The superintendency was a means, not the goal.

That orientation matters more than most people realize. And it shapes who teaches in the room, too.

KLR sessions are led by people who have actually done the job. Practitioners like Dr. Lu Young and Bart Flener, alongside currently serving and recently retired superintendents, walk participants through real scenarios they'll face from the superintendent's seat. This isn't theory delivered from a stage. It's honest, experienced insight shared by people who earned it. Every time I sat in a session and listened to what they were sharing, I learned something.

The content is remarkable.

Credential programs can produce administrators. They can't manufacture that kind of knowledge transfer or motivation. The people who are going to lead Kentucky's schools through the next decade need to be oriented outward, toward students and communities, not inward toward perception and position.

KLR selects for that from the start.

quality 2: It invests in the long arc, not the quick win

Rex Booth spent most of his career as a math teacher, basketball coach, school counselor, and principal. He was good at every one of those roles. He was also, by his own account, someone who never saw himself becoming a superintendent.

Then he joined KLR's first cohort.

He didn't walk out of the program with a superintendent's contract. He walked out with something harder to manufacture: clarity about who he was as a leader, and a network of people who could see what he was capable of before he fully believed it himself. The job came later.

That's what long-arc investment looks like. It's patient. It's relational. It doesn't promise a seat at the table: it prepares people to earn one.

Robert Braden, now the superintendent at Taylor County, described the program's structure as seven sessions focused on what it actually takes to be a superintendent. Not the theory of it. The life of it. Mock interviews. First-year success planning. Honest conversations with currently sitting superintendents about what the role costs and what it gives back.

You can't compress that into a weekend retreat or an online module. And you definitely can't replicate it at nearly three times the price without the relationships that make the learning stick.

quality 3: It builds on relationships and accountability, not checkboxes

Here's a question worth sitting with: what does a leadership program actually owe its participants?

A credential? Sure. But a credential is the floor, not the ceiling.

KLR was built on the premise that aspiring leaders deserve more than a certificate of completion. They deserve a room where they're known: where their gaps are named with care, their strengths are built on, and the people challenging them have actually sat in the chair they're trying to reach.

Tiffany Hicks described leaving one session and immediately returning to her superintendent to ask whether she could attend the next budget working session. And the construction meetings. She wasn't waiting to be invited. She was closing gaps she'd identified because the program helped her see them clearly enough to act on them.

One participant from this year's cohort wrote in their feedback that the experience was the most meaningful leadership opportunity of their career. They walked away with a stronger sense of confidence in their current role and the future ones they're working toward. Another described feeling a genuine kinship with leaders from across the state. A network they didn't expect, built in a room they almost didn't walk into.

That's accountability built into the design and not as a performance metric, but as a natural outcome of being in a room where honesty is the norm.

At Alchemy, we consider Reliable Oversight one of our core values. It means protecting trust through integrity, follow-through, and consistency.

KLR lives that out in the way it builds leaders: not by telling them what they want to hear, but by giving them what they need to grow.

quality 4: It sees people before they see themselves

This is the one that stays with me.

Rex Booth said it directly in his own words: he had strong mentors who saw something in him that he hadn't really seen in himself. They pushed him toward the superintendency. He's grateful for it today.

That sentence is doing a lot of work. Because what it describes isn't a program feature. It's a relational act. Someone looked at Rex Booth (math teacher, basketball coach, counselor, principal) and said, "You should be leading a district." And they said it before he believed it.

Jim Detwiler came into the program asking whether he had not only the skills but also the dispositions to do this job well. That question alone tells you something about the kind of person KLR attracts.

And for what it's worth, I interviewed Jim that December afternoon, and his energy was contagious. He's the kind of person who makes you feel like whatever room he's in just got better. He absolutely has the disposition.

These aren't people who showed up already certain. They showed up open and the program met them there.

This is what genuine pipeline development produces that credential factories never can: leaders who have been seen, named, and believed in before they had a title to validate it.

KLR's graduates are sitting in superintendent chairs right now.

That didn't happen because the program was slick or convenient or heavily marketed. It happened because Owens Saylor and Jim Flynn built something that was willing to do the slow, relational, unglamorous work of actually developing people.

And we got to help.

At Alchemy, we talk a lot about doing work that aligns with our values. That phrase can start to feel abstract after a while...something you say in a mission statement and then forget about on a Tuesday afternoon.

This work doesn't let me forget.

Being connected to KLR, from early conversations with Owens about what he was building, to a December afternoon taking headshots of people who are now preparing to lead school districts, to the ongoing work of helping the KASS team improve, iterate, and develop, has been one of the clearest reminders of why we do what we do.

Not every client relationship feels like this. But when you find work that connects to something you actually believe in, you hold onto it.

The fourth cohort is actively recruiting now. Sessions begin in October. And right now, we're working alongside the KASS team to build a graduate page, specifically for KLR alum, that aims to be a dedicated space where search committees and school boards can find and recruit KLR graduates as superintendent vacancies open.

The harvest from the early cohorts is already visible. The seeds being planted today are for the next generation of district leaders across this state.

We're glad to still be in the room.

If you're an aspiring superintendent (or you know one), learn more about Kentucky Leadership Rising at kysupts.org/KLR.

The people coming through that program will shape the future of education in this state.

It's worth knowing who they are.