NWAIS Spring Heads Meeting
May 3-5, 2026 Alderbrook Resort and Spa (Union, WA)
Speaker and Session Information
Announcing Keynote Speaker Jason Craige Harris, Polyanna Senior Advisor
Presenting: Leading with Steadiness Under Pressure: Practices for Reflective, Connected School Leadership
In a time of heightened complexity, school leaders are called not just to act—but to respond with steadiness, clarity, and care. This highly interactive session invites Heads of School to slow down, reflect, and practice what it means to lead well under pressure.
Drawing on storytelling, social science, and real-world leadership scenarios, participants will explore how to move from reactive postures to more strategic, values-aligned leadership. Through small-group scenario work and guided reflection, Heads will surface wisdom from their own lived experience, learn practical tools for “getting to the balcony” in difficult moments, and strengthen connection with peers.
Participants will leave feeling:
• More grounded in their own leadership instincts and wisdom
• More connected to one another through shared reflection and dialogue
• Better equipped with practical strategies they can use immediately in high-stakes situations
Designed as a welcoming, generative kickoff to the retreat, this session emphasizes application, peer learning, and thoughtful practice. About Jason Craige Harris, Senior Advisor, Polyanna Jason Craige Harris is an educator, speaker, facilitator, and leadership advisor who partners with K–12 schools to cultivate cultures of dignity, belonging, and transformation. A former classroom teacher and senior administrator, as well as a trusted coach to school leaders, Jason supports educators, administrators, students, and families in building trust, navigating conflict, and leading with purpose and care. Drawing on insights from ethics, psychology, and systems thinking, Jason helps school communities foster inclusive environments where all students and adults can thrive. He is a recognized expert in restorative practices and pedagogy, ethical leadership, and dialogue across lines of difference—and a sought-after speaker known for his powerful storytelling, deep empathy, and practical wisdom. Whether he is leading professional development for faculty, facilitating hard conversations among students, or advising senior leadership teams, Jason equips communities with the tools to prevent harm, repair breakdowns, and sustain a culture rooted in respect and shared purpose. And Workshop Sessions: Deep Listening: The Leadership Strategy Behind Authentic StorytellingThe most effective leaders start with questions. Whether you're new to campus, in a strategic planning cycle, or working to sharpen how your school shows up in the market, Step One is always the same: listen. "That's interesting — tell me more." This simple phrase is one of the most powerful tools in your leadership kit. When you lead with genuine curiosity, with staff and students, with existing and prospective families, you build the understanding that keeps you relevant and connected, which is the foundation for authentic messaging and stories that actually land. In this session, through case studies and real examples, we unpack the strategies behind deep listening and why it drives memorable, differentiated storytelling. Facts and figures are everywhere. What cuts through is a great story which begins with hearing from and listening to your audience.
In our time together, you will: - Explore a proven, replicable listening framework
- Discover how actual insights fuel the stories that make your audience say, "Tell me more."
- Chart your own path to listening, learning, and strategic storytelling
Expect stories, conversation, and time to workshop with one another With Barbara Egan, Head and Chief Strategist, StoryScape
With over three decades of experience across both large agencies and boutique firms, Barbara has collaborated with an array of clients spanning various industries. Before spending over ten years in education marketing, her most fulfilling role had been working with mission-driven organizations, serving as Global Director of Marketing for 1% for the Planet, a non-profit founded by Patagonia. Aligning what’s personal with professional purpose set the stage for where she is today. As a proud Loomis Chaffee and Rumsey Hall alumna, Barbara's career has come full circle—branding over 50 independent schools (and some higher ed) from coast to coast with her distinctive expertise forged in the very institutions that shaped her. & Culture in Action: Tools for Measuring Trust & Leading Change Independent schools are navigating increasingly complex change–new academic models, leadership transitions, schedule redesigns, wellness initiatives–often while trust, capacity, and clarity vary across teams. For mid-level leaders in particular, the challenge is acute: they are asked to lead change, translate decisions, and maintain culture without always having access to clear data or shared sense-making. Learn how to align strategic vision with the realities of school culture to support meaningful, sustainable change. This session introduces practical tools for understanding cultural readiness, identifying resistance, and strengthening trust within school communities. Drawing on organizational psychology and work in independent schools, participants will explore how to anticipate human dynamics during transitions, new initiatives, and organizational shifts. Leaders will leave with actionable strategies to engage people more effectively, reinforce alignment, and guide change with greater clarity and confidence.
With Cara Gallagher, Founder and Principal Consultant, Cara Gallagher Consulting (CGC)
Cara Gallagher is the founder and principal consultant of Cara Gallagher Consulting (CGC), a firm specializing in organizational culture, trust, and change readiness in independent schools. She works nationally with schools and associations to design listening strategies, leadership retreats, and custom change-management frameworks grounded in organizational psychology and real-world school dynamics. Cara is completing a master’s degree in Industrial-Organizational Psychology at Harvard and holds a prior Harvard certification in Organizational Behavior and Design. A former independent school educator and administrator, she brings a deep understanding of school culture and the realities facing leaders at every level. Her work focuses on helping schools move from intuition-driven decision-making to clearer, more humane, and more effective leadership practices.
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