Who Should Apply

October 21, 2025

8:30 a.m. - 3:30 p.m. ET,

KEDC, Lexington

If your answer is “for the glamorous meetings and interesting emails” you’re in for a surprise! This lively event requires you to dig deep as we explore the real motivations behind your interest in leading a district. Through candid stories, interactive activities, and a few confessions, you’ll reflect on your “why”—beyond the business cards and board reports. Whether you dream of making a difference or just want to know what you’re really signing up for, this is a day where you begin to define your all-important guiding principles and why you are responding to the superintendent’s calling.

November 18, 2025

4:00 p.m.  - 5:30 p.m., ET

Virtual

Finding the Right Fit is all about understanding and appreciating your leadership comfort zone. Sometimes, your comfort zone is exactly where you need to be, providing stability and clarity as you plan your next steps. In this session, we’ll explore what defines your comfort zone, how to recognize its value, and whether you have an interest or are ready to expand your horizons. We’ll engage in multiple activities to spark your thinking.  What are the advantages and disadvantages for leading your current district?  What are the advantages and disadvantages for moving to a new district as superintendent?

December 16, 2025

8:30 a.m. - 3:30 p.m. ET

GRREC, Bowling Green

Adaptive Leadership Part I kicks off a two-part series by diving into the groundbreaking work of Heifetz and Linsky and the practical wisdom of Your Leadership Edge. Dr. Jim Flynn and Coach Bart Fleener will lead as they unpack what it really means to lead adaptively—mobilizing people to tackle tough, ambiguous challenges rather than just applying technical fixes. You’ll explore how to “get on the balcony,” diagnose the difference between technical and adaptive problems, and experiment with new approaches to leadership. Expect candid discussion, real-world scenarios, and a few “aha” moments as you begin to build your adaptive leadership toolkit for today’s ever-changing educational landscape.

January 20, 2026

4:00 p.m. - 5:30 p.m., ET

Virtual

Recently, a significant change in expectations for superintendents has emerged. Rather than being just an effective communicator, superintendents now must be strategic messengers. This session explores why being a strategic messenger is a critical skill. While effective communicators get the message across, strategic messengers plan, tailor, and deliver targeted messages to specific audiences, aligning every word with district goals and community needs. In this dynamic online session, you’ll learn how to move from simply sharing information to shaping conversations and influencing outcomes. Discover the difference between “saying it well” and “saying what matters, to the right people, at the right time”—because in school leadership, strategy turns good communication into real impact.

February 17, 2026

8:30 a.m. - 3:30 p.m. ET

OVEC Shelbyville Conference Center

Adaptive Leadership Part II builds on Part I by shifting from understanding challenges to taking purposeful action. In this interactive session, you’ll learn how to identify where your leadership interventions can have the greatest impact and how to engage your team in tackling complex, adaptive problems that don’t have easy solutions. Drawing on key insights, you’ll practice strategies to mobilize stakeholders, experiment with new approaches, and navigate the discomfort that comes with meaningful change. Prepare to strengthen your leadership skills and turn adaptive challenges into opportunities for growth and lasting impact.

March 17, 2026

4:00 p.m. - 5:30 p.m., ET

Virtual

One of the more important sessions of the series, this virtual convening pulls back the curtain on the realities behind the title. From navigating tough decisions and late-night board meetings to balancing personal and family demands, this session explores the challenges that come with the job, including the loss of privacy, moments of isolation, and the delicate dance with school boards. But it’s not all stress and sacrifice. Through honest conversations and shared experiences, you’ll discover how superintendents find resilience, build support systems, and create meaningful impact. Walk away with a clear-eyed view and confidence to lead with purpose and heart.

April 14, 2026

8:30 a.m. - 3:30 p.m. ET

UK Next Generation Learning Center, Lexington

This session sheds light on one of the most critical—and often underappreciated—roles of school district leadership: Advocacy for Children and Families. Beyond the school walls, superintendents must collaborate with legislators, local leaders, and school boards to advocate for the best interests of students and those who support them. Dr. Flynn and others will unpack the art of speaking up for your district, building relationships, and navigating the political landscape to secure resources and shape policy. Most new superintendents aren’t fully prepared for this level of responsibility, but it’s a significant part of the job—and one where your voice can truly make a difference.

June 9th, 2026

12:30 p.m.

Lexington Country Club, Lexington

The KLR Celebration Luncheon is the grand finale you’ve earned and a definite program highlight. Join us for a celebratory lunch marking your completion of the Kentucky Leadership Rising program. Your superintendent is invited to share in your achievement, alongside the Kentucky Superintendent of the Year, KASS president, and other distinguished guests. The highlight: awarding of the Superintendent Readiness Certificates, recognizing your hard work and growth. Enjoy great food, inspiring company, and well-deserved applause as you take your next step in educational leadership. Mark your calendar now—this is a milestone moment you won’t want to miss!