ParentSquare began with a simple, deeply held belief: every family—no matter their schedule, language, or background—deserves to feel connected to their child’s school life.

What started as a grassroots effort in just four local schools has since grown into a platform that supports over 20 million family-teacher connections across the country.

But along the way, I’ve learned something important: technology alone isn’t enough. True family engagement doesn’t happen by accident—it takes intention. It takes systems, routines, and a shared commitment to making families feel seen, heard, and valued.

That’s why I started this guide. 

Whether you’re a district leader, a school administrator, or a teacher in the classroom, my hope is that this month-by-month roadmap helps you move beyond one-way updates—and into real, ongoing partnership with the families you serve.

And like ParentSquare itself, this is a living guide—built to evolve with your feedback, questions, and ideas.

Inside, you’ll find templates, tools, and practical ideas—but more than that, you’ll find heart. Because our goal isn’t just to communicate better. It’s to build something better—together.

Let’s begin.