In this fascinating episode of We Not Me, Dan and Pia step into a leadership world that many listeners may know little about: the US public school system. Their guests, Dr. Kristen Weikle, Superintendent of McLean County Unit 5 in Illinois, and Denise Pontrelli, former superintendent and executive coach, reveal the extraordinary complexity of leading educational systems that serve thousands of students, families and community members.
With responsibility for nearly 13,000 students across 24 schools, Kristen's role extends far beyond education. From finance and transportation to communications, infrastructure, staff engagement and community relations, she operates as the CEO of a complex ecosystem with profound influence on the future of her community.
The conversation explores how leaders can navigate complexity, avoid the myth that they must have all the answers, and build high-performing teams that work in sync towards a common purpose.
Key Topics Discussed
- What a US school superintendent actually does and why the role resembles that of a CEO
- Leading a district serving nearly 13,000 students across urban, suburban and rural communities
- The importance of stakeholder management across students, families, staff, taxpayers and local businesses
- Why effective leadership is about multiplying capability rather than being the expert
- How executive coaching helps senior leaders create space for reflection and growth
- The role of Squadify in helping leadership teams improve alignment, innovation and decision-making
- The power of purpose when leading through uncertainty and complexity
- Building cultures where teams challenge ideas, reflect regularly and take action
Key Quotes
"Ultimately, it's always about improving student outcomes." – Dr. Kristen Weikle
"You can get so much more done if you have a team of individuals that work together with you." – Denise Pontrelli
"We all need to be working towards achieving the goal and making progress together." – Dr. Kristen Weikle
"Squadify helps leaders be intentional about where they put their time and energy." – Denise Pontrelli"You don't have to be the expert in everything all the time." – Dr. Kristen Weikle
Three Leadership Takeaways
- Leadership Is Not About Having All the Answers: Both guests challenge the common belief that leaders must personally solve every problem. In highly complex environments, success depends on building capable teams and trusting their expertise.
- Purpose Is the Ultimate Compass: When operating in fast-changing, stakeholder-rich environments, purpose helps leaders cut through complexity. For Kristen and her team, every decision ultimately connects back to improving outcomes for students.
- Reflection Must Lead to Action: Data, discussion and feedback are only valuable when they drive meaningful change. High-performing teams create deliberate moments to pause, reflect and then commit to specific actions.
Resources Mentioned
I Really Needed This Today – Hoda Kotb
A collection of short, inspiring stories and reflections offering perspective, encouragement and moments of gratitude.
The One Percenters: How to Get Things Done Now – Darrell Mann and Shannon Finnegan
A practical guide to creating focused, high-performing teams capable of delivering meaningful results and implementation.
Multipliers – Liz Wiseman
Referenced by Dan and Pia in the reflection segment, this leadership classic explores how leaders can amplify the intelligence and capability of those around them rather than unintentionally diminishing it.
We Not Me Reflection
One of the strongest themes from this episode is the danger of the "hero leader" mindset. Faced with immense responsibility, leaders often feel pressure to grip tighter, make more decisions and become the centre of everything. Yet Kristen's success comes from doing the opposite: creating alignment, trusting expertise and enabling leadership throughout the system.
As Denise observes, sustainable leadership is not about carrying the burden alone—it's about creating the conditions where teams can flourish together.
For any leader facing complexity, uncertainty or rapid change, this episode offers a powerful reminder:
The goal is not to become indispensable. The goal is to build a team that can achieve more together than any individual could alone.
Guest bios
Dr. Kristen Kendrick-Weikle has spent her entire career in Illinois public education, moving through the classroom, special education leadership, and the principal's office before becoming a superintendent in 2011. She led Warrensburg Latham CUSD #11 for nine years before taking the helm at McLean County Unit 5 School District in 2020, where she remains today. Along the way she earned a doctorate in Educational Leadership from Western Illinois University, researching how Illinois teachers use differentiated instruction — a topic that still shapes how she thinks about school leadership.
Denise Pontrelli built her career in Minnesota schools, rising from teacher leadership roles into district administration and eventually the superintendency at Stillwater Public Schools. After leaving the district seat, she moved into consulting and organizational design, first at SiteLogIQ and now as CEO of her own firm, PartnerED Consultants, where she works on leadership development and executive coaching for educators. She holds graduate degrees from the University of Minnesota in both teacher leadership and K-12 administration.