| | | | Dear Friend, It's tempting to believe that school culture resets in August. New calendars open, fresh goals are announced, and everyone returns hoping for a stronger year ahead. But the healthiest communities know something important: next year is not built in August. It is built right now, in May. May is when a community has the clearest view of itself. We see where relationships are thriving and where trust has frayed. We know which efforts created momentum and which quietly lost energy. We see who feels connected, who feels unseen, and where fatigue has replaced patience. These are not failures. They are insights and opportunities. Too often, schools rush to the finish line and postpone reflection until summer. But by then, valuable information can be lost in the speed of year-end celebrations. May offers a rare opportunity to pause while the experience of the year is still fresh. This is the moment to ask: - What helped our community feel stronger this year?
- Where did we grow in kindness, courage, and connection?
- What tensions remain unresolved?
- Who still needs to feel more seen, heard, and valued?
- What must we carry forward, and what must we leave behind?
The strongest communities do not wait for a crisis to examine culture. They build habits of reflection, honesty, and care. They do not react, they anticipate. Before the final bell rings, take stock. Listen closely. Name what matters. Decide what comes next. Because next year does not start in August. It starts now. If your school is ready to reflect on this year and plan intentionally for the next, Pollyanna would be honored to partner with you through workshops, leadership planning, assessments, volunteer training, conferences, and community-building strategies rooted in Building Stronger and Kinder Communities. Warmly, | |  | | | | | Parent Program for Volunteer Leaders After working with many schools to strengthen parent volunteer leadership, Pollyanna has codified our most effective strategies into a new Pollyanna Parent Program for Volunteer Leaders. Designed for Parents Association leaders, admissions ambassadors, advancement volunteers, and other key parent partners, this program equips volunteers with the tools to lead with purpose, build connection, and elevate the parent experience across your community. Bring this program to your school in 2026-27 and invest in the parent leaders who help shape and represent your community. | | | | | | Circle Membership Begins July 1 Year-Long Learning. Stronger Communities. One Annual Fee. What does it look like to support your entire school community not just for a moment, but across an entire year? The Pollyanna Circle Membership is designed to do just that. Beginning this summer, your school will have access to the programs, tools, and conversations needed to Build Stronger and Kinder Communities with intention and consistency. This is a shared learning experience that strengthens your whole community. Gain expanded access to the resources schools rely on most from Pollyanna, including our full lineup of 20 workshops. Click to register. | | | | | | | | May's Final Workshops in the Series Join us for our two sessions until July's sessions begin: May 6: Paris and Shanie, From Policy to Action
May 14: Rosetta Lee, Parenting with Identity in Mind Both workshops offer timely, practical, and deeply relevant learning for this moment. We hope to see you on Zoom. These sessions conclude our 2025–26 Workshop Series. We also invite you to explore our 2026-27 Circle Membership, beginning July 2026 through June 2027, and discover the benefits of joining our community which includes full access to our 2026-27 workshops. | | | | | | Are you a Lifelong Learner? The Pollyanna Circle Membership offers year-round access to 20 live virtual workshops and on-demand recordings designed to help schools lead with purpose, strengthen culture, and respond to the challenges of the moment. Upcoming sessions feature expert facilitators, practical strategies, and meaningful conversations that support educators, leaders, and entire school communities in Building Stronger and Kinder Communities. Join us live or engage on your own schedule. Check out all Circle Membership benefits. | | | | | | Teen Council: Last Meet-up of 2025-26 Aaron Ray, Director of Opportunity Programs at Hamilton College, joins Pollyanna Teen Council alumni to share candid lessons on the college transition. With a decade of experience in access, equity, and student success, Aaron offers strategies for thriving academically and socially. Join us for our last meet-up of the school year and be part of this important discussion. Stay tuned for news from the Teen Council for 2026-27. New PTC leaders, new topics, new guests. We'd love you to be part of our meet-ups next year. If you're 13-18 years old and would like to join us next year, fill in this form and we'll be in touch. | | | | | | | | | | | | | | April was a Month of Momentum From partnerships and presentations, planning sessions and conversations, Jason and Casper had the privilege of spending time with leaders at BECDA, CAIS, Drew School, Dwight-Englewood School, Lake Forest Academy, Nantucket Lighthouse School, Poly Prep and The Spence School, to name some. The connection, thoughtful planning, and shared commitment to stronger communities made for an energizing month and a powerful reminder that change happens when people come together with purpose. We’re grateful for every conversation and excited for what’s ahead. | | | | Navigating a Culture of Fear Panel Our recent webinar, Navigating a Culture of Fear, offered a powerful reminder: fear may be present in school communities, but it does not have to define them. In a moment of real pressure and uncertainty, we explored what it takes to lead with steadiness, integrity, and alignment. Key themes included: clarity over certainty, trust through human connection, values-based decision-making, and the importance of leaders not transmitting fear to others. Leadership in this moment is not about eliminating fear. It is about not letting fear determine who we are with each other. | | | | | | Teen Council AI Take-aways Sam led a forward-looking discussion with the Teen Council exploring the intersection of AI and inclusion. Students engaged in thoughtful dialogue about the opportunities and risks of emerging technologies, how they are using AI, and how their school communities are navigating its presence in real time. The conversation also highlighted how much students are learning through shared discourse as they make sense of an AI-driven world and their role in shaping a more equitable future. Thanks, Sam! | | | | | | | | | | | | | | | | TeachAAPI Educator Circle™ TeachAAPI is a non-profit that supports educators with curated resources and professional learning centered on Asian American and Pacific Islander histories, identities, and contributions. It believes teaching AANHPI history is not just filling a gap, but showing America’s story is strengthened by every voice. TeachAAPI's Educator Circle™ offers a collaborative space for connection and growth with educators committed to this work. This summer, members will have the opportunity to take a Cultural Humility in the Classroom course to build confidence in teaching AANHPI content with depth, authenticity, and care. The training is led by DEI expert Tamisha Williams, an equity practitioner, coach, and facilitator with over a decade of experience. | | | | | | 10 STORIES FOR 10 YEARS We must be intentional with professional growth and classroom change. “Pollyanna workshops gave me confidence and courage.” Jennifer Vermont-Davis Read Jennifer’s full story on page 16 of our 10-Year Impact Brochure. | | | | A FINAL THOUGHT “The future depends on what you do today.” Mahatma Gandhi | | | | | | | | | | | | | Pollyanna, Inc. is a not-for-profit corporation 501(c)(3). © 2026 Pollyanna | New York, NY 10075 | | | | | | | |
