Frequently Asked Questions

Below please find a list of our most frequently asked questions from clients and partners. Do not see your question? Contact us and we’ll reply as soon as possible.

How was Pollyanna formed?

Pollyanna, a New York-based nonprofit, was formed in 2015, the project of Casper Caldarola, a former marketer with a deep commitment for promoting inclusiveness within communities. Since then, Pollyanna’s team has grown to include experts in DEI assessments, curriculum and programming. As educational institutions – and, by extension, society – undergo transformation in social justice, Pollyanna is uniquely positioned to help clients live their institutional commitment to DEI.

How do Pollyanna and clients work together?

Across the country, schools and other nonprofit institutions are working diligently to reshape cultures, promote equity, and deepen the work in anti-racism. Pollyanna empowers our clients to fulfill these goals.

How we work together depends on your needs. Some organizations use our DEI curriculum as a framework for their own. Others look to us to assess and benchmark their current DEI landscape. Others partner with us on intensive, yet transformative, summits and conferences. Our services are customized and tailored to your goals.

What can I expect working with Pollyanna?

Pollyanna is a small, nimble and resourceful team. Working together, you can expect personal attention and a program customized to meet your institution’s specific challenges. More than that, you can expect a team of compassionate and empathetic advisers, guiding you to make progress that is realistic, attainable and sustainable for the long-term, as any DEI program should be.

How does Pollyanna’s curriculum work?

Our K-8 Racial Literacy Curriculum – developed by a team of educators and available for free – is designed to help elementary school students build self-awareness and to empower them to engage in productive, and very age-appropriate, conversations about race and racism. Every school is different; some schools implement our curriculum in full, while others implement only components that are right for their school’s culture.

To address our nation’s systemic challenges, we must build in our children kindness, bravery and compassion, and to achieve this end, we must address taboo topics with courage and directness.

What do Pollyanna’s services cost?

Pollyanna is a nonprofit organization dedicated to promoting inclusiveness and equity within communities. In service to this mission, some of our services – our Curriculum and our Reports – are available free of charge. Other services, such as DEI assessments, conferences and workshops, and customized curricula, are tailored to meet our client’s unique needs and available resources.

What can I expect from a Pollyanna workshop?

Our workshops are tailored in support of each client’s goals, culture and the makeup of its participants. There is one constant — our workshop and facilitators are skilled in managing complex topics with directness, honesty, and compassion – the very characteristics we seek to build in the next generation of leaders, our children.

When is the right time to conduct a DEI assessment?

Our DEI Assessment is a snapshot in time – a measure of whether your school or institution’s culture is doing all it can to build empathy and compassion around topics of racism, inclusivity and cultural sensitivity. To move forward, we must know where we began, and setting a benchmark is a prudent first step.

How do I know if my institution needs to address systemic racism?

Systemic racism is just that – “systemic.” It permeates every aspect of our society and transcends person-to person interactions. The question isn’t whether our nation’s schools are burdened by systemic racism; the question is how deliberately and purposefully we are working to dismantle it and counter the effects, creating the most equitable environment for our students.

My child’s school is partnering with Pollyanna. What can I expect?

Pollyanna helps schools and institutions be more themselves; that is, Pollyanna helps them realize their cultural and DEI goals all while staying mission aligned. It isn’t a course-correction – it is an affirmation. Here’s what you can expect – you can expect a partner that strives for transformation through empathy. You can expect challenging, albeit vital, topics to be explored with directness yet compassion. And you can expect your children – all children – to be front and center in our joint efforts. We offer faculty professional development and parent workshops to support the curriculum that may be available at your school. Pollyanna also offers a Parent/Guardian Companion Guide to support an adult’s education.

Why is the organization named Pollyanna?

Pollyanna Founder Casper Caldarola named the organization in honor of her mother. Pollyanna was one of the nicknames she called Casper growing up, because she always tried to see the best in everyone.

Contact us with your questions.

Didn’t find your answer? Contact us with your question.

Contact Us: info@pollyannainc.org