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MAY 2025

Dear Friend,
 
“Thank you for this bit of sunshine in my inbox this morning. What fantastic news! I look forward to working with my school in support of attending this conference next year, taking place in my hometown! Onward!”
This was the very first email response we received after announcing Pollyanna’s inaugural National Conference—and it lit us up. That kind of genuine enthusiasm reminds us why we do this work.
As the school year begins to winds down, we’re filled with gratitude for recent moments of connection—from our local conference in Chicago to our Civil Rights trip to Alabama. These experiences affirmed how powerful it is when we come together with shared purpose.
Now, we’re turning that energy toward our next big gathering: Pollyanna’s inaugural National Conference, coming in January 2026. Designed for Small and Large School PODs made up of administrators, alumni, community engagers, faculty, heads of school, parents, high school students and trustees, this three-day event will offer powerful speakers, skill-building sessions, and space for deep, action-oriented connection.
Early pricing registration is open—details below. We can’t wait to welcome you to Minneapolis!
Warmly,
Casper Caldarola
Founder
 

LOOKING AHEAD

 

Meet Our National Conference Keynote Speakers

Jason Craige Harris – Conference Guide
Megan Hogan – Global Head of Talent, Goldman Sachs
Natosha Reid Rice – VP, Global Housing Opportunities and Mission Engagement, Habitat for Humanity International
Charles Vogl – Author, The Art of Community
Jamil Zaki – Psychology Professor and Author, Hope for Cynics

A special opportunity for the first 20 schools that register. Read our FAQs fine print - it’s worth a peek. Click here for more information.

 

Summer 2025 Workshop Series

This summer, bring your entire school community together for a transformative learning experience! Our 2025 Summer Workshop Series features 12 workshops designed to deepen alignment with your mission and values—and it's all available for one price per school.
✅ 12 impactful workshops
✅ 12 incredible facilitators
✅ One flat fee per school
✅ Open to your entire school community
✅ Designed to spark reflection and action

From Challenge to Change: Strengthening Teams and Departments in K-12 Schools

Creating thriving team cultures in a K-12 school requires more than good intentions—it demands intentional reflection, open dialogue, and collective commitment. This two-part series is designed to help teams and departments surface key challenges, foster trust, and develop actionable solutions that strengthen collaboration and communication.

See Resource below for more information.

 
 

Final Teen Council Meetup in May

Join us on May 18 for our last meetup of this school year. Dré Finley, a dialogue facilitator and restorative practitioner will join our group for a discussion on the importance of the youth voice and speaking up for change. Bring your voice!

If you're between 13-18 years old and interested in joining us, email info@pollyanna-us.org and we'll share the Zoom info.  

 
 
 
 
 

LOOKING BACK

What is the Admissions Department's Role?

On April 9, Joanna Lovett, Admissions Director at Drew School in San Francisco shared many suggestions on how to create more inclusion during the admissions process. Her 4 take-aways are:
1. Revisit Your Mission—Often and Intentionally 
2. Engage and Build the Capacity of Your Whole Community
3. Build Equity Into Every Step of the Process
4. Make People Feel GOOD! 
 
 

Pollyanna's first Civil Rights Trip in Alabama

This was an unforgettable 3-day experience with an inspiring group of friends and educators from CA, NJ, NY, and VA. Together, we walked across the Edmund Pettus Bridge, visited Bryan Stevenson's Equal Justice Initiative, and gathered at the Brown Chapel AME Church. Deep reflection, shared learning, and powerful moments of connection.

Reply to this email and let us know if you'd be interested in joining our Spring 2026 Civil Rights Trip to Alabama.

 
 
 
 

NNMS's Inaugural Conference

Near North Montessori in Chicago marked an inspiring milestone: their inaugural Pollyanna Conference – Pathways to Belonging. With keynote speaker Jason Craige Harris leading the way, we explored critical conversations on building connection, resilience, and stronger communities -- keeping dignity at the center. A powerful day of learning and action! Special thanks to HoS Angela Garcia and Director of Equity, Inclusion and Community Engagement Denise Boswell.

 
 

The Business Case for Equity & Inclusion

David Smith led an insightful session on how independent schools can strategically align fundraising, tuition models, and DEIB, and secure long-term sustainability. Key takeaways:
1. Tuition increases are fueling an affordability crisis, threatening socioeconomic diversity.
2.  Schools should replace traditional financial aid narratives with a focus on using the discount rate to support student excellence.
3. School heads should promote coalitions of DEIB staff with CFOs, enrollment managers, and advancement directors to collaboratively shift the financial model.

 
 
 
 

RESOURCE

From Challenge to Change: Strengthening Teams & Departments in K-12 Schools

Session 1: Naming the Barriers
Participants will engage in a 90-minute facilitated conversation to explore unspoken tensions, recurring challenges, and cultural dynamics that may be limiting team effectiveness. Through structured reflection and dialogue, we will identify patterns that shape the team experience and set the stage for meaningful change. To ensure an open and productive conversation about what may be standing in the way of the culture you aspire to create, we will use a carefully designed facilitation process. As part of this process, participants will have the opportunity to share anonymous reflections that will inform our discussion. Excerpts from these reflections—without attribution—will help guide our dialogue.

Session 2: Building the Path Forward
With a clearer understanding of the roadblocks, this 90-minute session will focus on generating practical solutions and making commitments that drive positive cultural shifts. Teams will collaboratively outline strategies to enhance trust, accountability, and shared purpose, ensuring that insights from Session 1 translate into sustained improvements in team dynamics and school leadership.

By the end of this series, participants will leave with a deeper sense of alignment, clarity, and a roadmap for building a culture where all members feel valued, heard, and equipped to lead effectively.

To learn more and book these sessions, email info@pollyanna-us.org

 
 
 

ENDORSEMENT

"Integrating Pollyanna Racial Literacy into our K-8 Program of Inquiry has enriched our IB and Reggio-inspired curriculum, deepening connections to identity, diversity, and equity. It empowers students to engage thoughtfully with multiple perspectives, while supporting teachers in fostering inclusive, meaningful conversations that enhance our Units of Inquiry and classroom culture."
 
Alejandra Navarro (she/her)
Director of Community Engagement and DEIB, La Scuola, CA
 

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