Introduction
Why Family Engagement Matters
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.
Anu Vaid
Founder & President
Have ideas on how we can improve the guide? We’d love your feedback—share with us here.
Introduction
Why Family Engagement Matters
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.
Anu Vaid
Founder & President
Have ideas on how we can improve the guide? We’d love your feedback—share with us here.
Preparing for the New Year
The school year doesn’t start in August—preparation, planning, and thoughtful setup need to start much earlier. The summer months are critical to laying the foundation for a successful communication year. By taking action now, you set the stage for a year where communication feels intentional, not reactive.
Your Goal: Set your district and schools up for communication success by cleaning up systems, organizing groups, refreshing templates, and ensuring alignment.
Top 3 Takeaways:
- Create groups that parents can join. Do not send everything to everyone. Set up groups that families can join based on their needs and interests (PTA, Athletics, Clubs, Volunteer Teams, etc.).
- Establish Weekly Communication Days. Create a predictable rhythm by assigning specific days for communication, such as “District Tuesdays” and “School Thursdays.”, so families know when to expect important information and look out for the digest that day.
- Encourage Families to Download the App. The mobile app offers the best ParentSquare experience—instant alerts, easy access to posts, messages, calendar events, forms, and more. Promote app downloads early and often.
Ready to dive deeper?
Explore the full chapter for practical checklists, sample posts, templates, and strategies you can share with your team. From cleaning up contact data to launching your first newsletter, this chapter helps you turn summer planning into a school year built on trust and consistency.
Available as a printable PDF.
Back-to-School Communications
First impressions to students and families matter. After all, you only get one! August is your opportunity to welcome families into a new school year, build trust, and establish communication norms. Now that foundational tools and templates are in place, it’s time to execute. This chapter includes guidance and communication norms you can provide to schools and teachers for a successful year.
Your Goal for August
By the end of the month, families should:
- Feel genuinely welcomed by the district, school, and teacher
- Know how to use ParentSquare (or your centralized app) to stay connected
- Receive timely, consistent communications from multiple levels
- Be connected to key interest-based groups (e.g., PTA, Celebrations)
- Begin responding to posts, signing up for events, or completing forms
Explore the full August chapter for checklists, sample welcome messages, templates, survey ideas, and celebration strategies. Whether you’re launching your district newsletter or helping a teacher make their first post, this chapter supports your team in turning back-to-school excitement into communication success.
Let’s turn first impressions into lasting connections.
Available as a printable PDF.
Building Attendance Habits Early + Sustaining Connection & Routines
September is when first-day energy turns into everyday habits. This month is all about helping students and families settle into consistent attendance, trusted communication rhythms, and routines that last all year. With Attendance Awareness Month as the backdrop, you have a perfect opportunity to reinforce why “every day counts” while keeping families engaged and informed.
Your Goal for September
By the end of the month, families should:
- Understand the importance of daily attendance and feel supported in building healthy routines.
- Be actively engaged in school groups, volunteer opportunities, and events.
- Know where to find information about classroom activities, field trips, and extracurriculars.
- Feel confident in how to communicate with teachers and schools.
- Be ready for upcoming touchpoints like Back-to-School Night and parent-teacher conferences.
Explore the full September chapter for checklists, campaign ideas, sample messages, and tips from ParentSquare users. Whether you’re running an attendance challenge, launching community groups, or preparing for conferences, this month is about turning routines into results.
Let’s turn consistent connection into stronger outcomes.
Available as a printable PDF.
Engagement Beyond the Classroom – Coaches, Clubs & More
October is when student life truly expands beyond the classroom. Sports, arts, and clubs are in full swing, making this the perfect time to help families stay connected to extracurricular opportunities. It’s also the month for mid-semester parent-teacher conferences and seasonal events like Halloween—key moments to deepen trust and ensure every child feels supported both academically and socially. With ParentSquare, schools can simplify communication for coaches, advisors, and teachers while keeping families informed, engaged, and included.
Your Goal for October
By the end of the month, families should:
- Be connected to at least one extracurricular or club group in ParentSquare.
- Receive clear schedules, reminders, and updates from coaches, advisors, or activity leaders.
- Use ParentSquare for sign-ups, forms, and payments related to activities and events.
- Feel prepared and supported for mid-semester parent-teacher conferences.
Explore the full October chapter for checklists, sample messages, campaign ideas, and best practices from ParentSquare users. Whether you’re helping a coach simplify team updates, preparing for conferences, or planning inclusive seasonal events, this month is about engaging families beyond the classroom.
Let’s turn extracurricular energy into stronger family connection.
Available as a printable PDF.
Gratitude, Giving & Community
November is the season of appreciation and connection. It’s the perfect time to thank staff and families, highlight student-led service, and share holiday plans.
Your Goal for November
By the end of the month, families should:
- See authentic thank-you messages from leaders and teachers.
- Participate in food drives, fundraisers, or service projects.
- Have clear info on holiday schedules and resources.
- Be introduced to new school board members and early bond conversations.
Let’s celebrate gratitude and strengthen school-community bonds this season.
Available as a printable PDF.
Celebrations, Community & a Strong Start After Break
December is one of the most activity-filled months of the year. From classroom celebrations and winter performances to holiday messages and end-of-term updates, families rely on ParentSquare to stay organized and connected. It’s also an important time to set clear, caring expectations for attendance before and after winter break—helping students return ready and supported in January.
Your Goal for December
By the end of the month, families should:
- Receive clear schedules and updates for classroom parties, performances, and events.
- See inclusive holiday greetings and school-wide messages that strengthen community.
- Know when school resumes and why showing up before and after the break matters.
- Feel supported with reminders, resources, and two-way communication during the transition.
Let’s wrap up the year with joyful celebrations and a smooth, well-supported return to learning.
Available as a printable PDF.
New Year, New Goals & a Strong Reset for the Semester
January is a natural restart point for schools and families. After winter break, districts use this month to re-establish routines, refocus on academics, and help students ease back into learning. Families rely on ParentSquare for clear schedules, weekly updates, mid-year conference planning, and supportive attendance reminders that rebuild strong habits. It’s also the ideal time to launch re-enrollment forms and ensure websites and resources are ready for a busy spring.
Your Goal for December
- Strategies to reset routines and re-establish consistent communication after winter break
- Templates for weekly academic updates and mid-year conference planning
- Supportive attendance messages for a positive restart
- A mid-year ADA website review checklist
- Messaging ideas for winter clubs, enrichment programs, and schedules
Let’s start the year with clarity, consistency, and a strong return to learning.
Available as a printable PDF.
Inside This Chapter
February brings focus on how clear, timely family communication helps schools support participation in events, conferences, book fairs, attendance routines, and early planning for next year — all while reinforcing trust and belonging.
You’ll find practical guidance on:
- Communicating expectations around February events and celebrations
- Supporting attendance through timely, supportive outreach
- Coordinating conferences and Book Fairs with clarity and consistency
- Helping families navigate re-enrollment, course selection, and planning
This chapter is designed to help schools focus less on launching new initiatives — and more on making it easy for every family to participate in what’s already happening.
Available as a printable PDF.Coming soon…
Coming soon…
Coming soon…
Have ideas on how we can improve the guide?
We’d love your feedback—share with us here.