2025 Award Recipient
Cheryl Booker
Cheryl’s Idea: Co-creating culturally grounded strategies with family child care providers to ease children’s transitions into kindergarten.
Cheryl is passionate about helping children in family child care settings transition smoothly into kindergarten, recognizing that this shift can be overwhelming without proper support. As a former kindergarten teacher and elementary school administrator, she has witnessed how excluded providers often feel from the transition process despite knowing the children best, while families worry and children face new routines without adequate support. This project serves as her response to honor those voices and co-create tools that help children feel confident and connected from day one of kindergarten.
Cheryl is eager to learn which tools and strategies best support emotional readiness and reduce anxiety in children as they transition from family child care into kindergarten. She looks forward to gaining deeper insight into how co-created, culturally grounded approaches—like visual schedules, goodbye rituals, and transition kits—are received by families and providers, and which are most impactful. Cheryl is also curious about how these tools can be adapted across diverse communities and how to effectively build bridges between family child care and elementary school systems. This learning will help shape a scalable, equity-focused model for supporting school transitions in early childhood.
Pilot Year Impact
For 2025 Imagine Award recipient Cheryl Booker, easing a child's transition to kindergarten meant looking beyond the child — to the educators, families, and schools around them.
Last year, Cheryl launched "Tiny Pilots for Big Change" in Prince George's County, Maryland, co-creating culturally grounded strategies with early childhood educators to ease children's transition from family child care into public kindergarten.
The heart of the pilot was a specialized resource kit packed in clear backpacks, developed together with educators and families.
Each kit included child-focused tools to build routines and manage emotions and a parent folder with a literacy guide and conversation starters to help families stay engaged at home.
Building genuine trust with families opened up honest conversations about their real challenges. Cheryl also saw how meaningful it is to create spaces where historically excluded providers feel heard.
As the pilot evolved, Cheryl realized the project was about more than creating transition tools. It became an opportunity to strengthen relationships between family child care educators, families, and schools, while elevating the voices of family child care providers as valued partners in preparing children for kindergarten. Ultimately, the pilot demonstrated that successful kindergarten transitions depend not only on preparing children, but also on intentionally connecting the adults who support them.
By the end, Cheryl engaged 8 educators, 3 coaches, and 27 children, with families connected to 14 receiving schools.
Receiving the $20,000 in funding provided Cheryl with the critical funds to compensate educators, purchase children's resource kits, and host their end-of-program celebration.
Beyond the financial support, the award offered invaluable coaching support that built her professional confidence, empowering her to pursue future funding and champion early childhood equity.
Q&A with Cheryl
We recently sat down with Cheryl to hear what she learned from her pilot and how Promise shaped her work.
Here are some highlights from our conversation:
What did you learn from your pilot?
“As I was doing the pilot, there's a lot that we tried and I say we, because it was collective, right? I'm working with the educators – we're co-creating together. What I did learn is they know their children the best and they know their families best. I did come with ideas and I was open to hearing them, which they appreciated. And so some of the ideas I had for the design of the book bag, changed based on what they said. And some things I wasn't even thinking about and they would come up with ideas – even the type of book bag that they wanted. They wanted it to be clear. I wasn't thinking that way.
The toolbox, for instance, what would go in it – the picture of a sleeve that's clear that they could put pictures of their families in there, just little components that they came up with that I didn't think about. And then just knowing how to engage the families is something that I learned how to do within this setting. I worked with families before but these were their families, these were their children and they knew best how to engage them, how to get them to talk with me because – who am I? They don't know me personally, so I wanted to be able to get their trust and they would open up and talk to me about some of the challenges that they were having. So I learned to listen. I learned to listen to others.
I learned to create a space where every voice is heard and everyone matters. And so when you leave my space, you feel that you were heard and that you matter and the surveys shared that. So I was really happy to see that. I learned to step back because as an administrator, you have a tendency to want to put your foot in everything and make sure, but I learned to step back so that others could be leading as well.”
How did the Imagine Award's funding and support help you and your pilot program?
“The educator's time needed to be compensated. These are professionals – these are business owners – wanting to make sure that they were compensated for their time and they were wanting to make sure that families who took an hour or two hours of their time were compensated for their time as well. When we had our celebration, we were able to provide a wonderful venue. All the children had their t-shirts, their book bags, their matching gear. We were able to provide that for them as well. We were able to make sure that the educators were highlighted – that their programs were highlighted. So the designing of our little logo and all those pieces, that could not have happened [without the funding].
Promise as a [funding] organization was so caring – they made sure you had everything you needed to be successful. They prepared you, they encouraged you, they created a space so you can have a conversation, and have people checking in on you – and not to check in on you like, "I'm not sure you're doing what you're supposed to be doing” but really checking in on you. [Saying] what do you need? What can I give you?
The coaching that was provided, they looked at us as professionals, but also we were family…it was evident [that they were] trying to get you to think out of the box, to think bigger, to dream a little. And so they provided that space for us. And some people probably were [more] familiar with entrepreneurship, not me. My thing was – I'm working full-time here. I really didn’t know much about [entrepreneurship], but I was successful because of Promise.”
Learn More About Cheryl
Cheryl Booker is the Director of Professional Advancement for the Family Child Care Alliance of Maryland and an Instructional Coach with the ASPIRE program. With nearly four decades of experience in early childhood and elementary education, Cheryl has served as a kindergarten teacher, Reading Recovery specialist, consulting teacher, staff development leader, elementary principal, and adjunct professor. She brings deep expertise in child development, adult learning, and culturally responsive instructional practices. Cheryl is especially passionate about equitable school transitions and empowering family child care educators and families as co-creators and partners in children’s early learning journeys. Now, as Director of Professional Advancement with the Family Child Care Association of Maryland and an instructional coach for FCC educators, she partners closely with providers and families to elevate their voices in the transition process.