Ready for the new school year? How planning ahead, providing explicit expectations, and implementing consistent practice with support can help students achieve independence and success.
Author: DJ Matsko | Dean & Content Teacher
Getting Ready for the New School Year
The other day, as I walked into my local Target, I looked up to see the big hanging advertisement for “Back to School Supplies” pointing past the freezer section toward a corner with shelves of pencils, pens, backpacks, notebooks, and lunchboxes. I thought to myself, “It’s not even August!”
But as I considered this thought, I had a flashback to my own days as a kid and remembered how quickly the month of August descended. Before I knew it, I was grabbing my supply lists and schedule for the new school year and in the throes of “Back-to-School” shopping. Other than deciding what outfit I was going to wear, I didn’t give much thought to anything prior to stepping inside for the first day of school.
Now as I enter my ninth school year at Winston Prep New York, I find myself thinking long and hard about how to support students, teachers, and families with ways they could set themselves up for a successful new school year.
As an Academic Dean, I have numerous conversations with members of the school community about what a huge transition “Back to School” really is. While we give our students and ourselves patience and grace, remembering what a shift it is to go from school year to summer to new school year, there are some steps we can take to be more prepared.
I have found it common for students and families to get caught up in summer plans and miss the opportunity to give the upcoming school year some serious thought. I hope these three back-to-school tips can provide you, your family, and your children with a helpful runway as the school year gets off the ground.
Successfully Navigate the New Year with Self-Reflection
One of the Qualities of a Sustainable and Independent Learner (QSIL) that I spend a significant amount of time emphasizing both inside and outside of the classroom is Self-Reflection. Implementing self-reflection time with your child about the previous school year is an effective way to start the conversation about the new one quickly arriving.
What daily routines worked well last year? Was it helpful attending Study Hall every Tuesday and Thursday? Did you enjoy going to Cooking Club after school on Mondays? In turn, these conversations can yield ideas for goal setting, supporting both personal growth and academic success.
Talk with your child about what goals or intentions they have for the new school year. Link those goals to a discussion of why they’re important, how they might tie to their learning, and which tools can be used to achieve those goals.
For example, if your child has a goal of being ten minutes early to school, asking them why this is important will help them to develop the intrinsic motivation necessary for achieving that goal. Knowing that time management, prioritization, and organization are facets of executive functioning that your child is working on can also help them to develop strategies for achieving their goal.
Perhaps they will benefit from a morning routine checklist or timers that indicate when it's time to get out the door. Maybe they can coordinate a travel buddy system for additional accountability. All of these strategies taken together enable your child to remain more goal-oriented intrinsically, meaning a greater chance of successfully reaching their goals!
“Know Before You Go” - Reading the Student and Family Handbook
Every year, families are required to fill out multiple forms, including the acknowledgement of the Student and Family Handbook. While many of the sections of the handbook remain the same year after year, some policies and procedures change or go through periodic updates.
Let’s be honest, it would be grueling work for many of our kids to read through this incredibly long (and at moments, dense) handbook. That said, it’s important for them to understand the policies that pertain to them.
One way to do this effectively is to break the handbook down into a series of small chunks (just like we do with readings in class!) and take time to read sections aloud with your child. Use it like a Read Aloud activity where you and your child each take turns reading.
Given that the handbook is lengthy and that some sections may not directly apply to your child, a strategic approach is helpful. First, make sure the essential expectations are covered. For example, the sections about attendance, technology, student conduct, and dress code are sections that can take priority and be covered together. Additionally, allow time for your child to process the information and to ask questions. Some sections will need to be re-read.
Finally, use this time as an opportunity for developing self-advocacy: as your child asks questions, make a plan for how they can address these questions and concerns with their teachers.
This practice of reading the handbook together as a family not only prepares you for what to expect for the upcoming year but also covers a series of skills, including reading fluency, critical thinking, self-advocacy, productive discourse, and more!

“Get in the Groove” - Starting Back-to-School Routines Early
Countless studies and years of research have shown the benefits of consistent structures and routines, especially for students with learning differences. We also know that initiating new routines or transitioning from one routine or structure to another can be incredibly difficult for our kids.
In your August conversations about the upcoming school year, consider initiating a conversation with your child about how and when to implement school year routines prior to the start of the school year. As before, with goal setting, ask your child why these kinds of routines might be important and what tools are available to ensure they are carried out. For example, have conversations around
screen expectations and
digital wellness.
What time will technology be put away in the evening to “wind down” before bed? When will bed time be? When will homework be completed? What does the morning routine look like?
Make a list of considerations together with your child to collaborate on the plan for the year. If your child feels as though they have a say and have been a part of the planning process, they will be much more likely to invest in following the plan. Perhaps some of these routines will be helpful for the whole family!
Fostering Student Success and Independence
This is by no means an exhaustive guide for preparing for Back-to-School. However, my time at Winston has demonstrated how planning ahead, providing explicit expectations, and implementing consistent practice with support and flexibility along the way can help students meet their goals and achieve independence and success.
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