A Conversation With Debra P. Wilson, President of NAIS
Debra Wilson, president of the National Association of Independent Schools (NAIS), took an unconventional path into education leadership. After law school and a start at the Department of Justice, she staged what she calls a “self-intervention” and asked what work would truly fill her cup. The answer led her to NAIS, where she spent nearly 20 years moving from regulatory work into governance, risk management, and organizational leadership. After serving as president of the Southern Association of Independent Schools, including leading through the pandemic, Debra returned to NAIS as president.
Her journey offers a useful reminder that there may be no wrong step, just the next one. Sometimes the best leadership move is recognizing when it’s time to find a different trail.
Episode Takeaways
- Build strategy with people, not for them. Debra's team engaged staff and members throughout strategic planning, creating shared meaning before the polished plan ever appeared. Agreement is easier when people receive a strategy. Alignment gets stronger when they help build it.
- Going slow can help you go fast. Debra has a bias toward action, but she recognizes that transformation requires time to build clarity, common language, and commitment. Otherwise, leaders risk adding more initiatives while wondering why nothing moves.
- Acknowledge the messy middle. Transformation asks people to sustain existing work while building new capabilities. Leaders need to recognize that reality, provide resources, and make trade-offs rather than quietly piling more onto already-full plates.
- Treat boards as learning ecosystems. Healthy board alignment requires more than good governance hygiene. Board members need context, education, clear expectations, and meaningful opportunities to contribute strategically. Simply telling someone to “be strategic” is not much of a strategy.
- Lead with clarity, culture, and empathy. Debra encourages leaders to simplify communication, build shared language, pay attention to culture, and get curious when someone responds unexpectedly. Misalignment may be signaling something people believe is at risk.
Debra leaves us with an invitation to align around curiosity. Imagine bringing together people with dramatically different perspectives to explore how education works around the world, then asking a bigger question: If we could build education again from the ground up, what would we create? Alignment doesn’t require everyone to arrive with the same answer. It creates the context for people to wrestle with important questions together.
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Dr. Julie Williamson wrote the book on how to Make HOW Matter. After working with hundreds of executives and leadership teams at Fortune 500 and S&P 500 companies, she created the Make HOW Matter Accelerator™ to bring the power of leadership alignment to more leaders at every level.
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Dr. Julie Williamson wrote the book on how to Make HOW Matter. After working with hundreds of executives and leadership teams at Fortune 500 and S&P 500 companies, she created the Make HOW Matter Accelerator™ to bring the power of leadership alignment to more leaders at every level.
Grounded in both real-world business experience and social science, this virtual, self-paced program helps you turn the principles of Make HOW Matter into practical leadership skills you can use every day. Whether you’re a small business owner, leading a division, or simply looking to increase your influence and drive better results, you’ll learn how to close the gap between agreement and true alignment, and turn priorities into action. Ready to make HOW matter? Explore the Make HOW Matter Accelerator™.
Learn more about Julie and Karrikins Group:
Creators and Guests
Host
Julie Williamson, PhD
Julie Williamson, PhD is the CEO and a Managing Partner at Karrikins Group, a Denver-based, global-serving business consultancy. Author, Keynote Speaker, and Host of The Failure Gap Podcast, Julie is a leading voice in how alignment can transform leaders and organizations.
Guest
Debra P. Wilson
In 2023, Debra P. Wilson became the ninth president of NAIS. In addition to leading the organization in partnership with the NAIS Board of Trustees, she provides support and education to member schools. Wilson speaks frequently on topics such as leadership and governance, school operations and financial sustainability, community health and well-being, and the future of schools. She also serves as a key spokesperson, representing the independent school voice in broader educational conversations. Before becoming president of NAIS, from 2019 until 2023, Wilson served as president of the Southern Association of Independent Schools (SAIS), where she led the organization through a period of growth and supported school leaders in her region through the COVID-19 pandemic. Her SAIS role followed 19 years at NAIS as general counsel. In that capacity, she oversaw advocacy work for the organization, supported schools in crises, advanced best practices in governance, and created legal advisories along with other informational resources. Before joining the NAIS staff, Debra was a tax litigator at the Department of Justice. In addition to serving on the boards of several independent schools, Debra’s current board service includes The Enrollment Management Association (EMA), the International Council Advancing Independent School Accreditation (ICAISA), and the Council for the Advancement of Private Education (CAPE), of which NAIS is a founding member. Wilson is also co-author of the NAIS Trustee Handbook (10th and 11th editions) and regularly contributes to the NAIS Trendbook, Independent School magazine, and other industry publications. Wilson received a B.A. in English from Sewanee: The University of the South and a J.D. from the University of South Carolina. She is a proud graduate of the Williams School, an independent school located on the campus of Connecticut College. She is an avid reader, photographer, and cook who loves to be outdoors.
