Kentucky Leadership Rising is a statewide initiative designed to elevate, equip, and empower the next generation of education leaders. Led by the Kentucky Association of School Superintendents (KASS), this effort recognizes that strong school leadership begins with strong support.
KASS plays a pivotal role in shaping Kentucky's educational future by empowering superintendents through targeted leadership development. Recognizing the complexities of their role—from navigating policy shifts to engaging diverse communities—KASS provides essential, forward-thinking training to ensure both new and seasoned superintendents are prepared to lead with confidence and clarity.
As the educational landscape evolves, Kentucky Leadership Rising ensures our leaders remain at the forefront of innovative practices, united by a commitment to student success. Through tailored resources, professional learning, and a strong, supportive network, KASS is proud to champion the leadership of all 173 superintendents and those rising to join them.
Together, we’re building a future where every child in Kentucky thrives.
ASPIRING SUPERINTENDENT WORKSHOP SERIES
The Kentucky Leadership Rising Aspiring Superintendent Workshop Series is a personalized, in-person learning experience designed for certified, aspiring, and underrepresented leaders across the state. Hosted regionally and grounded in authentic dialogue, each session offers mentorship, skill-building, and connection to a statewide leadership network. Participants walk away with practical tools, renewed confidence, and clear next steps for advancing their leadership journey.
In service and support of Kentucky’s future school executive leaders, registration is open for KASS’s nine-part Aspiring Superintendent’s Workshop Series titled Kentucky Leadership Rising, set to convene its third cohort in October 2025.
01
Online Orientation
Date: October 14, 2025
Time: 4:00–5:30 p.m. ET
Format: Virtual
Kick off the series with an overview of Kentucky Leadership Rising, connection to peers, and guidance on what to expect from the year ahead.
02
Why Do You Want to Be Superintendent?
Date: October 21, 2025
Time: 8:30 a.m.–3:30 p.m. ET
Location: KEDC, Lexington
Explore your leadership purpose, assess your readiness, and reflect on the core motivations behind your desire to lead a district.
03
Finding the Right Fit
Date: November 18, 2025
Time: 4:00–5:30 p.m. ET
Format: Virtual
Learn how to evaluate district culture, community needs, and leadership alignment to determine where your leadership will thrive.
04
Adaptive Leadership I
Date: December 16, 2025
Time: 8:30 a.m.–3:30 p.m. ET
Location: GRREC, Bowling Green
Dive into the foundations of adaptive leadership: how to lead through complexity, build trust, and navigate change effectively.
05
Superintendent as Strategic Messenger
Date: January 20, 2026
Time:
4:00–5:30 p.m. ET
Format:
Virtual
Learn how to communicate with clarity and purpose across stakeholder groups, media, and challenging moments.
06
Adaptive Leadership II
Date:
February 17, 2026
Time:
8:30 a.m.–3:30 p.m. ET
Location:
OVEC Shelbyville Conference Center
Continue building adaptive leadership skills with a focus on coalition-building, resistance management, and practical application.
07
The Real Life of the Superintendent
Date:
March 17, 2026
Time:
4:00–5:30 p.m. ET
Format:
Virtual
Get real about the superintendent role, from crisis response to political pressures, and hear directly from current leaders in the field.
08
Superintendent as Advocate for Children and Families
Date:
April 14, 2026
Time:
8:30 a.m.–3:30 p.m. ET
Location: UK Next Generation Learning Center, Lexington
Focus on advocacy strategies to uplift student and family needs, influence policy, and use your role for systemic impact.
09
KLR Celebration Luncheon
Date: June 9, 2026
Time: 12:30 p.m. ET
Location:
Lexington Country Club, Lexington
Celebrate your growth, connections, and leadership journey with peers and mentors in a culminating luncheon event.
WHO SHOULD REGISTER?
Kentucky Leadership Rising is designed for certified, aspiring, and underrepresented leaders who are working toward a future as a Kentucky superintendent, whether that next step is months or years away.
This highly interactive, nine-part workshop series is not a certification course. Instead, it offers a practical, real-world approach to leadership development. Sessions are led by experienced former and current superintendents, featuring authentic scenarios and strategies leaders face every day. With a blend of in-person and virtual learning, participants will deepen their skills, expand their networks, and prepare to lead with confidence and clarity.
Space is limited.
Secure your spot today and take the next step in your leadership journey.
READY TO RISE?
Cost: $1,000
Your registration includes:
- Exclusive access to all nine sessions
- All program materials (books, resources, and products)
- Prizes and incentives awarded throughout the program
- Exclusive use of the KASS Superintendent Dashboard
- Lunch and refreshments provided at each in-person event
- EILA credit for each session (6 hours or 1.5 hours per event; 30 total hours)
- Invitations to attend the KASS Fall 2025 and Summer 2026 Superintendent Summits at no cost
- Celebration Luncheon in June 2026
- Display-worthy plaque with Certificate of Superintendent Readiness
- Opportunity to earn Platinum Achievement Recognition
- Formal letter of support for use in application materials
- Unlimited job search coaching and advisement

SESSION DESCRIPTIONS
Each session in the Kentucky Leadership Rising Aspiring Superintendent Workshop Series is intentionally designed to build critical leadership skills through real-world scenarios and reflective practice. Participants will engage with experienced superintendents, gain practical tools, and leave each session more prepared to lead with clarity and purpose.
ONLINE ORIENTATION
October 14, 2025
4:00 p.m. - 5:30 p.m. ET
Meet your cohort members and program facilitators and learn important details about the KLR program in this virtual convening. It will be important to take notes! Be ready to be challenged with the “Cohort Quiz” at the end.
WHY DO YOU WANT TO BE A SUPERINTENDENT?
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.
FINDING THE RIGHT FIT
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?
ADAPTIVE LEADERSHIP PART I
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.
SUPERINTENDENT AS STRATEGIC MESSENGER
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.
ADAPTIVE LEADERSHIP PART II
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.
THE REAL LIFE OF THE SUPERINTENDENT
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.
SUPERINTENDENT AS ADVOCATE FOR CHILDREN AND FAMILIES
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.
KLR CELEBRATION LUNCHEON
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!
BEYOND THE SESSIONS
REAL-WORLD READINESS FOR THE SUPERINTENDENT ROLE
APPLICATION STRATEGIES
Craft standout applications that showcase your leadership story and vision. Learn how to tailor materials, highlight your unique strengths, and avoid common pitfalls so your application rises to the top of every superintendent search committee’s stack.
INTERVIEWING TIPS + TOOLS
Master the art of the superintendent interview! Discover how to anticipate tough questions, communicate your value, and turn nerves into confidence. Leave with practical tools and memorable strategies to make your next interview your best yet.
BUILDING AN EPORTFOLIO
Showcase your leadership journey with a dynamic ePortfolio. Learn what to include, how to organize artifacts, and ways to make your digital presence pop—so districts see your impact before you ever walk in the door.
WORKING WITH A SCHOOL BOARD
Unlock the secrets to effective school board relationships. Explore strategies for collaboration, managing conflict, and building trust—so you can turn your board into your strongest allies in leading district success.
FILLING READINESS GAPS
Superintendents are expected to be knowledgeable about most everything that happens in the district. Identify and close your “blind spots” and areas of inexperience. Through self-assessment and targeted planning, discover how to strengthen skills, fill experience gaps, and ensure you’re truly ready for the broad challenges ahead.
ENSURING A SUCCESSFUL YEAR ONE
Set yourself up for a stellar start! Discover proven strategies for navigating your first year as a superintendent, from building effective relationships to setting priorities and achieving results. Demonstrate your willingness to listen and learn from day one.
SHIFTING FROM MANAGER TO LEADER
Move beyond checklists and calendars to inspire real change. Discover how to transition from managing tasks to leading people, shaping vision, and cultivating a culture of excellence across your district.
LEADERS IN THE FIELD
Hear directly from experienced superintendents who’ve walked the walk. Gain candid insights, practical advice, and a few cautionary tales from those leading Kentucky schools—so you’re prepared for what’s next.
