Every PCD student is assigned an advisor upon matriculation to Middle or Upper School. In the Middle School, each grade level has a team of advisors comprised of faculty who teach in that grade and are familiar with the subtle differences among the four middle school years. Middle school students are paired with new advisors each year. In the Upper School, advisors are members of the teaching faculty or administrative staff. Ninth grade students are assigned advisors who have been trained to provide guidance and support for students in this pivotal, transitional year. Students are paired with new advisors in the tenth grade and will stay with their advisors through graduation. In both divisions, each advisor works with an average of seven students.

The advisor plays an important role in a student's school life. New students meet their advisors on their first day of school, and continue to see them each day during homeroom, a time when many advisors will "check in" with their advisees. In the beginning of the school year, students and advisors participate in an off-campus outing with their grade level as a way of strengthening community ties. Over the course of the school year, each advisor attends sporting, arts, and other events in which their advisees are involved.

The advisor is seen as the first point of contact between families and the school. Advisory groups meet regularly to discuss school-wide issues, such as the course selection process or to review the student handbook.  Advisors also meet with advisees individually to review academic progress and discuss each student's specific questions and needs. Advisors help students select a rigorous curriculum that takes into account individual interests and strengths, and provides the strongest possible preparation for college. Often the advisor is the faculty member who knows the student best, from the most diverse perspectives, and can be the student’s strongest advocate for success across multiple venues.

Conferences are conducted twice a year between advisors and parents, but advisors are available throughout the year to address concerns and refer parents to those in the community who can offer additional support as needed.