Partnering for the Journey: Middle School and Grade 9 Parent Orientations Launch the Year

Head of School Ryan S. Dahlem opened the program by capturing the vibrant spirit of the school year’s kickoff. He specifically highlighted the high-energy Red & White competition and the bonds formed when upperclassmen high-fived Rivers' younger students during exciting rounds of trivia games. Reflecting on the long-term impact of the Middle School experience, Dahlem reminded families that “the days are long, but the years are short,” noting that the Class of ‘27 student body co-presidents began their Rivers journey in the Middle School and the future co-presidents are sitting among the current Middle School classes. 

Dahlem outlined key school-wide priorities, including the new balanced daily academic schedule, a focus on the transition from the Middle School to the Upper School, and expanded wellness resources and programming. He also shared updates on the school’s Strategic Plan, announcing that early campaign planning and a feasibility study validated three fundraising priorities for an ensuing campaign: 1) a transformational new community center that will complete the main quad, establish a reimagined entrance to campus, and serve as a vibrant hub for student gatherings, community life, and the performing arts; 2) an increase in endowment to support financial aid, professional community excellence, and program innovation; and 3) continued support for annual giving to provide program enhancements that impact Rivers students every day.

“We are very excited to partner with you on your child's Middle School journey and a successful transition to Upper School,” Dahlem said. “It’s a time when they are developing core academic skills and finding new areas of interest, all while exploring the timeless question of ‘Who am I?’" 

Head of Middle School John Bower P’31, now in his nineteenth year at Rivers and speaking as both an administrator and an eighth-grade parent, opened by grounding the evening in connection. He introduced parents to Big Small Talk, an orientation exercise originally developed for eighth graders. In the student version, Middle School students interview faculty members on their very first day back, organize their notes, and deliver public introductions in front of eighty peers and teachers to build collaboration and public speaking skills right from the start. Parents participated in a scaled-down version, pairing up by grade level to ask questions and exchange practical advice. 

Bower drew a parallel to the Middle School journey by sharing stories from last June’s trip to Italy with thirty-one middle schoolers, where some of the richest learning occurred when things didn’t go as planned—such as navigating a delayed city bus in Rome or realizing that peperoni in Italian refers to bell peppers rather than meat. “The trip, for me, is a wonderful metaphor for what we're trying to accomplish in Middle School: establishing a strong foundation of skills and habits so students can adapt, problem-solve, and thrive when real life doesn’t always follow a script,” Bower said.

Bower also shared insights from last spring’s survey of eighth-grade students, parents, and caregivers, which highlighted strong feelings of belonging and community fostered by advisory programming, strong student/teacher relationships, and experiential trips such as Chewonki and Washington, D.C. In response to survey feedback, Middle School leaders are also ensuring students are accountable to academic expectations as they prepare for the transition to upper school through structured unit assessments, a gradual reduction of scaffolding, and increased independence over the course of the three years. 

Underscoring his partnership with Head of Upper School Colleen Kyle, Bower highlighted a strategic initiative to ensure that students experience a genuinely coherent journey from Grade 6 through Grade 12. Working alongside the academic leadership team, they are mapping out a progression of skill development from middle school through Grade 9 and beyond. This work aligns with a shared whole-school approach to teaching and learning anchored in three commitments: developing autonomy, building belonging, and cultivating purpose. Referencing Rebecca Winthrop’s book The Disengaged Teen, Bower explained that clearly defining skill expectations helps encourage students to take ownership of their learning.

Assistant Head of Middle School and Grade 7 math teacher Meredith Lorber shared her perspective on early adolescent development, drawing on over two decades in education. Acknowledging the social awkwardness and rapid physical, emotional, and cognitive shifts of the middle school years, Lorber highlighted the natural beauty of this age, emphasizing that adolescents bring deep curiosity and a passion for justice. 

In an initiative to provide clearer feedback about student academic progress, Lorber introduced a redesigned report card structure created over the summer to separate non-cognitive habits from discipline-specific academic mastery. The new reports measure student habits on a frequency scale and evaluate course benchmarks on an independence scale ranging from beginning to extending, with the expectation that most middle schoolers will land in the developing or meeting stages. Homework expectations will also scale gradually—from 60 minutes per night in Grade 6 to 90 minutes in Grade 8—to reinforce learning and foster executive functioning skills.

Middle School Dean of Student Life Sarah Heffrin closed the presentation by talking about student wellness and social-emotional growth. Defining leadership as being your best self and positively influencing others, Heffrin framed the middle school years as a naturally bumpy ride where minor missteps, like forgetting an instrument or spilling lunch, offer crucial opportunities to build resilience. She encouraged parents to give kids time and space to process difficult days before stepping in, while keeping open lines of communication with advisors along the way. 

“Autonomy, belonging, and purpose aren't things a school builds in silo. The school-to-home partnership is strongest when the lines of communication remain open,” said Bower. “We can better support your child when we're working with as much of the full picture in place as possible.”

On September 28, Upper School families gathered for the Grade 9 Parent Orientation, an evening set up to demystify the high school transition and provide families with practical strategies to support their students through the freshman year. 

Head of Upper School Colleen Kyle opened the program and welcomed parents by framing the importance of intentional support for students during the transition from Grade 8 to 9. She introduced Grade 9 Dean and math teacher Christine Pynchon, whose career at Rivers has spanned 13 years. As the person who greets all 99 students during morning attendance, Pynchon shared that she “looks forward to getting to know them better as individuals over the course of the year.” 

Drawing on her experience in both the classroom and the dean's office, Pynchon acknowledged that entering ninth grade is a major shift as students navigate unfamiliar academic systems, new social norms, and the pressure of being new, all at once. Recognizing that parents often bear the weight of their children's exhaustion, one-word grunts, or end-of-day frustrations, Pynchon offered a key piece of advice: "Do not get on the roller coaster." Referencing the children's book The Rabbit Listened, she reminded parents and caregivers that while other animals offer unsolicited advice or rush in to analyze problems, the rabbit simply sits and listens. Pynchon encouraged parents not to rush to fix every setback, emphasizing that genuine learning happens in moments of challenge and stepping back reassures students of their own capability to handle difficult situations.

Dean of Student Life Krista Sahrbeck then explained the role of student advisors and introduced 12 senior student advisors who guide ninth graders throughout the year. These seniors host small-group check-ins, serve as familiar faces on campus, and act as a vital bridge to adults for extra support. 

Following the opening remarks, parents rotated through three breakout sessions focused on academics, social, and extracurricular activities. In the student life session, senior panelists—representing a broad range of pursuits from varsity athletics, theater, and music to niche clubs like debate, yearbook, and philanthropy—emphasized the importance of stepping outside one's comfort zone early on. Reflecting on their own experiences, seniors recalled signing up for numerous activities at the annual club fair, noting that joining JV teams, affinity groups, or arts productions led to some of their closest friendships and strongest sense of belonging. They pointed to low-pressure settings—like the third-team soccer roster, club blocks built into lunch, or grade-night gatherings—as a place where genuine community develops. When asked about social dynamics and school spirit, the seniors pointed to all-school assemblies and tradition-building events like Friday Night Lights as moments where they truly felt connected to the school.

Addressing academic life and balance, the student panel offered reassuring perspectives on managing workload, high expectations, and time management. Seniors explained that freshmen learn to use designated free blocks, study halls—where the first portion of time is focused on quiet, concentrated work—and resources like the tutoring center in the library to keep up with assignments during the school day. Most importantly, they stressed that "at Rivers, it's ok to ask for help." Panelists shared anecdotes about overcoming early academic hurdles, including an AP Physics test score of 33 percent that ultimately rose to an A- after adjusting study habits, and a late-night email to a teacher for an essay extension during an athletic trip to a distant school, which was met with total teacher empathy. 

Seniors added that relationships with teachers often start with a simple conversation after class or a quick email, and those connections frequently lead to long-term mentorships through junior and senior year. The event concluded with seniors sharing practical, hands-on advice on organization, sleep hygiene, and phone boundaries—leaving parents with a clear, encouraging picture of the support system awaiting their ninth graders.