Stories from the Stoop: Think Big, Act Small – Leadership In Action at Kairos
- Dr. Khalil Graham
- 5 days ago
- 5 min read
Pull Up a Chair
When I started Stories from the Stoop, my goal was simple: to create a space where we could reflect openly on where Kairos has been, where we’re headed, and what we’re learning along the way.
This year feels especially meaningful. We’re graduating our first class, opening new doors for students, and sharpening our identity as a school. These milestones remind us that Kairos is no longer the scrappy startup it once was—we’ve matured into a community with deeper roots, stronger systems, and bolder aspirations.
At the same time, we know our success depends not on grand gestures but on consistent, daily actions that keep us aligned and focused. That’s the heart of our theme this year: think big, act small.
Where We Started
When I arrived in the 2022–23 school year, Kairos was juggling a lot at once: new leaders at the network and school-level, a new high school, and the ongoing challenge of building strong systems at our existing middle school.
Flexibility and agency got us through those early years—but they also meant too many decisions lived with one person at a time. Information was siloed. Systems weren’t always clear. We were constantly reacting instead of planning ahead.
Over time, we’ve learned how to balance our entrepreneurial spirit with the kind of structures that free us to focus on kids, culture, and growth. We’re not a big district—and we don’t want to operate like one. But we’ve grown enough to know that clarity creates capacity.
That clarity underpins our three priorities this year: 1) financial stewardship and strategic growth, 2) strong middle school foundations, and 3) student persistence and enrollment.
Lessons Along the Way
Growth hasn’t come without bumps. We’ve seen firsthand how missing enrollment projections affects resources in classrooms, how compliance gaps strain relationships with our authorizer, and how focusing too much externally can mean missing critical internal needs.
The lesson is clear: our short-term focus and long-term strategy have to stay connected. When systems and culture are pointed in the same direction, everyone knows what matters most, how progress is measured, and how their work ties into the bigger picture.
We’ve already seen this pay off. This year, more realistic enrollment goals led to better resource allocation. Dedicated compliance support cleared concerns with our authorizer. And by streamlining leadership roles, we sharpened our focus on what matters most: winning for kids, every day.
Evolving Leadership at Kairos
That’s why we reshaped our leadership model last year—making the senior team smaller, shifting the strategy team inward, and putting more weight behind principals as front-line leaders.
It comes back to a simple truth: winning for our kids comes first.
Supporting principals, giving them space to lead while backing them with strong systems, and tightening the connection between campus and network leadership have made us stronger. Neither school leaders nor network staff can succeed alone. We win when both succeed—together.
This partnership is also how we’ll build strong middle school foundations this year: by ensuring our principals have both clarity and autonomy, and that our network provides the scaffolding for their success.
Financial Discipline and Values
Last year, we took a bold step forward with the launch of our high-paying teacher first compensation model — a decision rooted in who we are becoming: a network that values its people and invests in quality. When our authorizer acknowledged our financial progress, it was a reminder that leading schools takes both courage and competence.
We made this investment because we believe great schools start with great educators. But with that bold move came a deeper responsibility: to manage our finances with the kind of daily discipline that makes such commitments sustainable.
That balance — precision in the details, alignment with the big picture — is where we’re continuing to grow. Every dollar has to keep classrooms resourced and schools running smoothly, while also fueling long-term priorities that strengthen Kairos for the future.
This is the heart of our Financial Stewardship & Strategic Growth priority for 2025–26. Strong systems ensure we use resources wisely; bold vision ensures we invest in people, programs, and possibilities that drive better outcomes for kids.
Seeking Context and Staying Close
Graduating our first class is a huge milestone. It also reminds us that lasting success isn’t built in big leaps—it’s stacked in small, disciplined actions every day.
That’s why principals now sit at the table in step-backs and retreats, why we’ve built new communication channels, and why we’re cultivating a culture where candor and collaboration fuel better decisions. With Jonathan leading the Schools team and Adaure and Nick returning as experienced leaders, we’ve reached a new level of trust and shared ownership.
Moving network leaders into the CPH building reflects the same mindset. It wasn’t just about efficiency—it was about proximity. Being closer to classrooms, culture, and community keeps us grounded in what matters most. And it helps us strengthen the relationships that drive student persistence and enrollment.
Our Priorities for 2025–26
All of this momentum is pointed toward three priorities:
Financial Stewardship and Strategic Growth – Making strong choices today so Kairos stays healthy tomorrow.
Strong Middle School Foundations – Building the habits, knowledge, and confidence students need before they transition to high school.
Student Persistence and Enrollment – Living our belief that “once a Kraken, always a Kraken” by creating experiences that keep families connected and kids excited to stay.
These aren’t abstract goals. They’re lived out in the small things: the conversations you have with students and their families, the joy of house celebrations, the careful way you set up systems, the persistence you show when challenges arise. Every small win builds toward the big vision.
Think Big, Act Small
Kairos started as a dream—that if we brought together people who cared deeply about kids, we could do something transformational. That dream is still alive.
But achieving it now requires us to act small: to focus, to stay disciplined, to stack one good decision on top of another. Together, those daily actions add up to transformational change.
I believe deeply in this team. I see your heart, your effort, and your commitment. My promise as your CEO is to keep showing up—to listen, support, and clear the path—so we can keep moving forward together.
This edition of Stories from the Stoop is about alignment: honoring where we’ve been, naming what we’ve learned, and setting our sights on where we’re going. The road won’t always be easy, but our mission is worth it—and our people are up to it.
Let’s celebrate, learn, and grow together—one step, one decision, one win at a time.
