As the Stakes Get Higher, How Do We Support the Transition to High School?

Learning Heroes
6 min readMar 2, 2021


Helping Families and Educators Partner Up to Put Students on a Path to Success

by Melissa Rayworth

While working at a high school years ago, Robert Hendricks III faced a challenge: A teenager was struggling, and Hendricks was determined to help him make lasting progress.

The solution wasn’t one thing, but a mix of several. First, Hendricks got the student involved in a club at school to build the student’s sense of belonging. He also established home-school communication by staying in constant contact with the student and his parents through a four-way text chain. And he used total transparency — before texting updates, he would tell the student what those messages would include and help the young man plan the best way to discuss the details with his parents.

Hendricks also met regularly with the young man’s teachers for a clear narrative about how things were going. By sharing this solid, real-time feedback with the student, Hendricks set him up to reflect on the feedback and then lead conversations with the whole group about the next steps he would take to succeed.

The student knew he was being seen and heard. He knew he was surrounded by caring adult support. And yet, Hendricks says, this approach “let him be in the driver’s seat.”

Adults often see teenagers “and perceive them as adults that haven’t yet matured,” he says. “Whereas I see them as children who have matured. And that kind of shifts the mindset a little bit about the type of support they need.”

Hendricks, who today serves as founder and executive director of the nonprofit He is Me, shared that insight during the recent “Preparing for Postsecondary Success — As the Stakes Get Higher, How Do We Support the Transition to High School?” webinar, part of a free series co-hosted by Learning Heroes and Remake Learning Days Across America.

This webinar (available for replay here) was designed for teachers and school administrators, as well as out-of-school-time providers, parent leaders, and others who work with parents, caregivers, and families to advance educational and developmental outcomes for children.

It can be difficult to balance the work of supporting teens while also giving them space to take responsibility — especially with middle schoolers who are making the jump to high school amid the stress of the ongoing pandemic.

So this webinar paired Hendricks with Robert Crosby III (managing director at the Flamboyan Foundation) and Crystal Requejo (communities program manager of the Mexican American Unity Council) to explore concrete strategies, insights and resources that can help educators partner with families for real success in high school, with an eye toward future pathways.

Among the highlights:

It’s vital for educators to let families know they are valued as partners, and to make sure they know their input is welcomed and respected, Crosby shared. “We have to recognize the historical nature of distrust with families and school systems,” he said. If “we want them to show up when we want them to, how we want them to, then those are the conditions that really break trust.” As busy as teachers may be, they will find more success with students if they build trust through cohesive relationships with students’ support systems at home. Crosby shared Flamboyan’s REAL Family Engagement model designed to ensure that families get the information and connections they need to support their children’s success.

Requejo reinforced that message as she spoke about partnering with parents who may not have had the chance to attend high school themselves. In her work with first-generation Latino students in San Antonio, she finds that “many parents and their children are going through this process together,” she says. For all families, clear communication from their child’s school is a top priority, whether it’s helping parents understand what a GPA is or how to prepare their child for college and life beyond high school.

Requejo also spoke about acknowledging the powerful resilience and commitment to education found in these families. When the pandemic began, “we saw parents parked behind buses to get WiFi for their children,” she said. “They are creative. They’re innovative, and when it comes to their children’s education, they want the best for their child.” But Requejo, Crosby and Hendricks all agreed that parents can’t truly support their children’s learning unless they are welcomed as respected partners.

Panel moderator Windy Lopez-Aflitto spoke about what “family engagement” means — “It’s important to continue to debunk the myth that family engagement is just an elementary school thing,” she said, and to debunk the myth that Black and Brown families don’t care. “They absolutely care,” she said,“and will show up.” To keep parents engaged during middle and high school, educators can support parents as they take on the role of “coach” which looks and feels a little different than their role during the early years.

The stakes get higher as students get closer to graduation, so this isn’t a moment to let students sink or swim. Two-way, asset based communication around goals, grade level expectations, and student progress that includes parents + teachers + students is central to building student agency and co-creating plans for success.

The webinar audience got a first look at a new resource from Learning Heroes called Paths to Success. This research-based, bilingual resource is aimed at helping parents of middle and high school students prepare their children for success in high school and beyond — whether that path leads to a four-year college, technical program, or a job. It includes numerous resources to help with things like class choices, career pathways, financial aid and more. In addition to curated resources from trusted organizations like Khan Academy and EdNavigator, it connects parents to Learning Heroes’ Readiness Check, a free (bilingual English/Spanish) online tool that helps parents get a clear sense of their students’ grade-level readiness and connects families to videos, activities, and resources for skill-building at home.

The insights and strategies shared during this panel couldn’t come at a more important time. Recent research by Challenge Success and NBC News comparing high school students’ experiences from fall 2018 through fall 2020 found that students are experiencing increased stress and anxiety, are less engaged, and are more likely to report strained relationships.

Learning Heroes’ Parents 2020 survey also found that the top concern for K-12 parents was that kids are missing important social interactions at school or with their friends. It’s hard for anyone to estimate what the impact of that might be.

Parents clearly want guidance on issues ranging from motivation to academics — during Learning Heroes’ 2020 #ParentStrong Town Hall, the nonprofit received more than 5,000 questions from parents around the country — and the majority came from parents of middle school students.

This webinar and Paths to Success aim to help fill the gap in resources for families as their students make the important transition to high school and beyond.

Get connected to Paths to Success and learn more about “Preparing for Postsecondary Success — As the Stakes Get Higher, How Do We Support the Transition to High School?” by watching the webinar here.

Learn more about Remake Learning Days Across America and the regional festivals here.

And be sure to join us for upcoming webinars for educators and parents:

Finding Balance: Ideas and Resources for Working Parents During Virtual Learning

Make Summer Count: How to Keep Your Child Learning While Having Fun (offline and online!)



Learning Heroes

Learning Heroes serves to inform and equip parents to be advocates for their children and best support their academic, social, and emotional development.