Mastering Academic Transitions: Five Key Strategies for Supporting Your Child’s Journey - Greenwich Moms
Aron Boxer  M.Ed. S.P.E. is the Founder and CEO of Diversified Education Services (DES), a Greenwich-based organization that has been delivering academic and organizational support to students and professionals for over 15 years throughout Fairfield & Westchester Counties and beyond. Aron began his career as a special education teacher with Greenwich Public Schools and later served as the Director of Special Services at Greenwich Catholic School. He holds a master’s degree and certification in special education with a specialization in learning disabilities. Through his extensive experience, Aron developed a proven program methodology and assembled a team of top-tier experts who make up the DES team. Together, they empower clients to reach their academic, professional, and personal goals.
 
 
 
Aron’s expertise has earned him recognition as a trusted voice in education. He has appeared and contributed to Fox News, USA Today, U.S. News & World Report, Fox Weather, NTD News, News 4 New York, CT Insider, and numerous other national and regional outlets.
 
 
Here are five tips from Aron for how to support your child’s academic journey.
 
 

1. Establish a Transition Routine

If you’ve ever found yourself repeating the same five-minute warning, only to be met with pleas for “just a little more time,” you’re not alone. Transitioning from downtime to homework is a common struggle. Our kids are subject to high expectations, but without a clear routine, they can trip out of the gate, leading to lost, incomplete, or misunderstood assignments. Creating a consistent transition routine, like a set five-minute warning, or reminders from their devices can help students shift more easily between tasks, reducing the daily battle and making academic shifts smoother.

2. Strengthen Core Executive Functioning Skills

Transitions often challenge the executive functioning skills required to stay organized, plan, and manage time—crucial skills throughout their academic journey. In EF coaching, we refer to this ability to shift between activities as “set-shifting.” Kids with ADHD, learning disabilities, autism, speech and language impairments, or general executive dysfunction often find transitions particularly tough, whether it’s moving between different homework subjects or shifting from a play mindset to study mode. These skills become essential as students enter middle school, where navigating different classrooms and assignments requires increased organization and adaptability. The earlier they start working on these skills, the easier it becomes to meet rising academic expectations.

3. Build Self-Advocacy Early and Often

Self-advocacy isn’t just about speaking up; it’s about building respectful relationships with teachers to avoid unnecessary penalties. Students who struggle with executive functioning may miss deadlines, and once teachers’ patience runs out, students can face punitive consequences. I’ve seen this firsthand—students who delay communicating with their teachers or fail to reach out can find themselves with a “zero” on an assignment, which may significantly lower their grades. A respectful email to the teacher can bear fruit, but it’s not guaranteed.

4. Instill Resilience for Challenging Situations

Encourage your child to understand that while they can’t control others, they can control their responses. Sometimes they’ll encounter a teacher with whom they don’t jive, which can be discouraging. I’ve seen students receive harsh messages from teachers after simple misunderstandings, which can damage their self-confidence. I work with students to help them manage their reactions and find constructive ways to approach these situations—whether it’s writing a respectful follow-up email or clarifying their struggles. Building resilience in handling such challenges helps them take control of their academic journey, ensuring that a difficult relationship with a teacher doesn’t lead to unnecessary setbacks. Building self-advocacy early helps mitigate the challenges that they can overcome with support.

5. Guide Them Through Responsibility in New Environments

For ninth graders or those switching schools, the workload jump can be a rude awakening. Going from middle to high school or high school to college means facing a reality where parents can’t always swoop in to help manage assignments, and college professors won’t accept calls or emails from parents asking for leniency. Suddenly, kids are responsible not only for their homework but also for life tasks—like laundry—that might have previously been handled by a parent. Without early preparation, these transitions can leave both students and parents overwhelmed. Teaching responsibility early, whether it’s through organizing assignments or managing chores, prepares them for the new independence required at each academic level.

These strategies are more than just tools—they’re steps in shaping confident, capable learners. With support from the EF coaches at DES, these transitions can be less of a struggle and more of an opportunity for growth, paving the way for your child’s long-term academic success.

Written by Aron Boxer, CEO/Founder & Head Exectuive Function Coach & Learning Specialist of Diversified Education Services

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