episode-header-image

Today

39m 29s

Episode 285: The Future of School Leader...

About this episode

Up next

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 leadership team at Locust Grove Middle School in Locust Grove, Virginia—to reflect o ... Show More

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 work?In this special solo episode of Leaning Into Leadership, Dr. Darrin Peppard ref ... Show More

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 new administrators away from the work they were most excited to do: leading people ... Show More

Recommended Episodes

128 Sarah Levitt - Your Best Year Ever

<p class="p1">A new year. A fresh start. For many professionals, it signals a new beginning, such as seeking a new job or promotion. For others, it's a time to set goals. Goals that can make the upcoming year your best year ever. Sarah Levitt is a leadership coach. She works with ... Show More

Aspire Mailbag: Career Aspirations and Leadership Opportunities

In this Aspire Mailbag episode, Jeff Gargas and Joshua Stamper dive into listener questions about school leadership, connecting with students and staff, building future leaders, and navigating career aspirations. Topics include: How can you consistently connect with students and ... Show More

308. Finding Fulfillment in Leadership: Featuring Walter McKenzie

In this engaging episode of Aspire to Lead, we sit down with Walter McKenzie, author, ASCD leader, and co-creator of The Worthy Educator, to explore the complexities of leadership in education. Walter shares his thoughts on the temptation to say "yes" to roles because of titles, ... Show More

Become a World-Class Leader

What Happens When You Help Others Win

The first step toward helping someone become their best is to help them believe that they can. In this week's episode, John Maxwell shares the influential power of giving others a win! After his lesson, Mark Cole and Chris Robinson unpack his insights so you can apply them direct ... Show More

The Truth About Bringing Your "Authentic Self” To Work - A Leadership Coach Explains

Work takes up more of our lives than almost anything else—so it’s no wonder that it can leave us feeling drained, stuck, and oftentimes further away from who we authentically are. This week, JVN is sitting down with leadership coach and author Mory Fontanez to unpack what it real ... Show More

225 Tatia Granger - Working in Teams

<p>You look at your calendar and you see a Team Meeting is up next. How does that make you feel? Love them or hate them, we spend about a third of our work week working in teams. A Stanford University study found effective teamwork is linked to increased productivity. Harvard Bus ... Show More

737: How to Fundraise for Leaders Who Never Wanted to Fundraise, with Alice Ferris

Alice Ferris: GoalBusters Alice Ferris is the Founding Partner of GoalBusters, a firm working to help small and mighty fundraising teams achieve big impact by planning practical strategies, teaching essential fundraising skills, and doing the hands-on work to turn vision into rea ... Show More

Start with Yourself

<p class="MsoNormal"><span style= "font-family: 'Arial',sans-serif;">When it comes to life and leadership, one of the wisest pieces of advice comes from John Maxwell: "You have to start with yourself." At first glance, this idea might seem counterintuitive. We often associate gro ... Show More

Chapter 1: The Charismatic Leader

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