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Learning Specialists provide support in three crucial capacities:

1. With the guidance of the Learning Specialists, students learn about a variety of learning styles and experiment with various learning strategies in the classroom, then use various self-report forms to examine areas of success and difficulty. This strategy fosters an atmosphere of trust in which students are able to honestly express successes and concerns in a way that enables them to learn from each other in a spirit of confidentiality. To keep abreast of progress and address concerns Learning Specialist frequently meet with student individually.
2. Every day, there is a scheduled "Strategic Planning" period of 15 minutes, where the advisors, supervised by the Learning Specialist, ensure that each student has all necessary materials for daily homework and that she or he is setting and meeting short-term goals for long-term assignments.
3. Learning Specialists collaborate with teachers and students to ensure that material is presented optimally for their students in order to create classrooms that are compatible with student needs. Learning Specialists also remain actively involved with students to provide support for timely submission of assignments, areas of difficulty, and both short and long-term goal-setting.

One full-time counselor is primarily engaged in classroom guidance and provides a weekly check-in with students who need short-term monitoring. Students with long-term needs are referred for outside counseling. The department of Support Services also includes the Woodlynde School librarian, who teaches research skills to middle school students and consults with upper school teachers and students in the classroom when long-term papers are assigned.