The outplacement department at The Windward School plays a critical role in ensuring that students transition successfully into mainstream schools when they are ready. Led by Diane Kissner, the department takes a deeply personalized and family-centered approach to guiding students and their families through the outplacement process. With a strong emphasis on readiness, self- advocacy, and the invaluable benefits of Windward’s Study Skills program, Kissner and her team are committed to setting up students for long-term success.
For many families, the outplacement process begins in the spring of their child’s seventh-grade year. Students are typically planning for their transition after eighth grade at this stage, and the department provides them with essential guidance and structure. A crucial first step is an outplacement information session, which helps families understand the process and what to expect. Following this, each family meets individually with the department to discuss potential school choices and the student’s academic needs.
While school selection is an important aspect, Kissner emphasizes that the process goes far beyond simply matching students with schools. “We know schools. And parents know their child better than anyone,” she explains. “When we work together, it turns out really well.” The department carefully assesses not only a student’s academic capabilities but also independence and overall readiness to succeed in a new environment. With these factors in mind, families are encouraged to diversify their applications to schools so that each student has at least one strong placement.
The department encourages students to take initiative in the application process, from writing personal statements to preparing for interviews.
One of the key points Kissner stresses to families is the tremendous value of staying at Windward through eighth grade. That academic year at Windward marks a significant shift for students, where they are expected to take greater ownership of their learning and practice self-advocacy. “We want to see them start to use these tools a little bit more independently,” she explains. “There’s a stronger emphasis on self-reliance in eighth grade, and we really want the kids to step up and take care of themselves.”
A highlight of the year is Windward’s Study Skills program, a highly structured course that provides students with the research and writing tools they need for high school and beyond. Over the course of the year, students learn to analyze texts, take structured notes using keywords and phrases, and synthesize information from multiple sources into a well-organized research essay.
Beyond academic preparation, the outplacement experience fosters a sense of confidence in students. They leave Windward both with strong academic skills and the self-assurance needed to navigate new surroundings. The department encourages students to take initiative in the application process, from writing personal statements to preparing for interviews. Students gain valuable experience in presenting themselves effectively and professionally, with the ability to appropriately convey their strengths.
The department’s commitment to its students does not end once they are placed in a new school. Alumni frequently return to share their successes, seek advice, or address challenges in their new academic environments. Whether assisting a family in securing proper accommodations or providing support through unforeseen academic hurdles, the outplacement department remains a trusted resource. “Our families use us as a resource long after they’ve left,” says Kissner.
A unique aspect of Windward’s outplacement process is its whole-family approach. The department recognizes that transitioning to a new school is not just about the student; it’s also about the family unit as a whole. Families are supported just as much as students, ensuring that every step of the process— from school selection to application completion—is handled with care and collaboration. “This works best when we work as a team,” says Kissner. “We provide the options, but it’s up to the family to make the final decision.”With its deep commitment to student success, personalized approach, and ongoing support, the outplacement department at Windward makes sure that each child leaves the school not only academically prepared but also confident and self- sufficient. As Windward continues to grow, Kissner and her team remain dedicated to fine-tuning their approach, strengthening relationships with schools, and, above all, maintaining the trust of the families they serve.
