As with the other case studies in this journal, Ben Moudry and Andrew Christopherson present a vision of a Montessori high school that is focused on fostering the adolescent personality in connection to society. This chapter uses concrete examples of the key experiences and programs that provide the adolescents at The Grove School with this goal in mind. A list of desired outcomes for adolescents along with associated adolescent specific indicators is provided as these outcomes guide the work at The Grove School. [This talk was presented at the NAMTA Adolescent Workshop at the AMI/ USA Refresher Course, February 17-20, 2017 in Austin, TX.]