What does effective school leadership look like in a rapidly changing world?

In this episode of Leaning Into Leadership, Darrin Peppard sits down with Debra Wilson, President of the National Association of Independent Schools (NAIS), for a thoughtful conversation about leadership, organizational alignment, AI, demographic shifts, and the future of Education.

Drawing on more than two decades of experience supporting school leaders, Debra shares why today’s educational challenges require leaders to move beyond the traditional “hero leader” model and embrace the power of strong leadership teams.

Together, Darrin and Debra explore how schools can adapt to changing Family expectations, navigate increasing complexity, and create meaningful educational experiences that prepare students for an uncertain future.

In This Episode

• Debra’s journey from attorney to education leader
• The evolution of school leadership over the past 25 years
• Why leadership teams have become more important than ever
• The role of alignment in successful schools and organizations
• How demographic shifts are impacting education
• What leaders should be considering about AI and the future of learning
• The importance of creating meaningful educational experiences
• Why today’s students need schools to think differently
• A powerful leadership lesson about seeking perspective and support
• How leaders can build systems that create long-term success

Key Takeaway

“Nobody leads by themselves.”

As schools become increasingly complex, leaders who build aligned teams, seek diverse perspectives, and focus on creating intentional experiences for students and families will be best positioned to thrive.

About Debra Wilson

Debra P. Wilson serves as President of the National Association of Independent Schools (NAIS). Prior to becoming president in 2023, she served as President of the Southern Association of Independent Schools (SAIS) and spent nearly two decades at NAIS as General Counsel, leading advocacy efforts, supporting schools through crises, and advancing best practices in governance and leadership.

Connect with Debra Wilson

LinkedIn:

https://www.linkedin.com/in/debrapwilson/

National Association of Independent Schools:

https://www.nais.org/

NAIS LinkedIn:

https://www.linkedin.com/company/nais/

New View EDU Podcast:

https://www.nais.org/resource-center/nais-podcasts/new-view-edu

Connect with Darrin Peppard

Website:

https://roadtoawesome.net

LinkedIn:

https://www.linkedin.com/in/darrinmpeppard

Learn more about Coaching, consulting, keynote speaking, and leadership development opportunities through Road to Awesome.

Sponsor Spotlight:

This episode is sponsored by HeyTutor.

HeyTutor partners with schools and districts nationwide to provide evidence-based high-dosage tutoring support in Math and ELA while helping schools remain intentional about staff capacity and student support systems.

Learn more here: HeyTutor.com

Most Recent Episodes

June 21, 2026

Episode 284: Great Schools Start with Great Leadership Teams

What does it take to build a leadership team that truly works?In this episode of Leaning Into Leadership, Dr. Darrin Peppard sits down with Marlene Rombach, Rocio Rhoads, and Christina Shires—the...

Listen · 47:17

June 17, 2026

Episode 283: Leadership Is the Intentional Creation of Conditions

What if leadership isn't about carrying more?What if the true responsibility of a leader isn't solving every problem but intentionally creating the conditions where other people can do their best...

Listen · 13:12

June 14, 2026

Episode 282: The New School Leader's Playbook with Erika Bare & Tiffany Burns

Landing your first leadership position is exciting...until reality sets in.The meetings, the emails, the difficult conversations, the angry parents, and the constant interruptions can quickly pull...

Listen · 42:27

Load More Episodes

Darrin Peppard Dr. Darrin Peppard

Dr. Darrin Peppard is an author, leadership coach, consultant, and speaker focused on organizational culture and climate, and growing emerging leaders. Darrin is the best-selling author of the book Road to Awesome, and is the host of the Leaning into Leadership podcast. As a ‘recovering high school principal’, Darrin shares strategies and lessons learned from 26 years in public education to help leaders gain clarity, find joy in their work, and walk in their purpose.