A staple of the private school experience at Cheshire Academy is an advisory system. All students are assigned to small groups of 5-7 students that are led by faculty members. Advisors help guide students through their years at the Academy. Formal meeting times happen once a week, but most students see their advisors daily, sometimes just for a quick hello in the dining hall, passing between classes or in dorms. During advisor meetings, whether a formal group meeting or informal one-on-one meeting, advisors will discuss academics, athletics, social life and other issues relating to school life and life as a teenager in general.
Advisors are there to support their students when they need it, serving as mentors, advocates, counselors and support for their advisees, and are available to meet with students outside of formal advisee meetings. Advisors are an active part of student life, keeping track of academic performance, athletic and artistic endeavors, and general well-being. Sometimes, advisors provide guidance and then step back and watch the students learn and succeed on their own, while still checking in regularly. Other times, advisors take a more hands-on approach, giving more personal attention to the students who need and want it. This flexibility in working relationships is part of the student-centered experience, giving students the support they need when they need it.