Kathleen O'Leary
Retired, Former CEO - Wisconsin State Fair Park
Q: What unique qualities do you believe sets you apart as a leader and woman of influence?
A: With over 30 years of experience navigating complex challenges across public, private, non-profit, and government sectors, I bring a strategic, growth-oriented perspective to leadership. My career is marked by numerous firsts and achievements in organizational growth, operational optimization, and building high-performing, mission-driven teams. What truly sets me apart is my unwavering commitment to purpose, integrity, and innovation—qualities that have shaped both my leadership style and my influence in the community.
Q: Can you share a pivotal moment in your career that shaped your path?
A: A pivotal moment came in 1999, early in my tenure at Wisconsin State Fair Park, when a major power outage disrupted half of the fairgrounds with nearly 100,000 people on-site. I was tasked with leading crisis communications, managing internal and external messaging, and navigating intense media scrutiny. That experience tested my ability to lead under pressure and cemented my path as a trusted decision-maker. It also marked the beginning of what would become a dynamic and rewarding 25-year journey in leadership at the State Fair Park, culminating in my appointment as CEO, serving as the first female CEO from 2016 to 2021.
Q: How do you define leadership, and how do you embody those qualities in your own life?
A: I live by two guiding philosophies personally & professionally: 1. Never Burn a Bridge. Bridges represent opportunity, connection, and the ability to return. Even in difficult moments, I believe in ending relationships with respect and fairness—because paths have a way of crossing again. Taking the higher ground at all times plays into this philosophy as well. 2. Authentic, Servant Leadership. True leadership starts with humility, empathy, and integrity. It’s about empowering others, lifting them up, and helping them become their best selves. Whether I’m guiding a team, mentoring a colleague, or parenting my three daughters, I strive to lead with clarity, trust, and compassion.
Q: How do you pay it forward and support the next generation of leaders?
A: I believe in providing guidance rather than direction. Creating opportunities for others to explore, learn, and lead fosters new ideas and innovation. I aim to serve as a sounding board and mentor, emphasizing the importance of steadiness and offering encouragement to the next generation to help aid in finding clarity on their path forward.
