The U School is a district high school in the Innovation Network of Philadelphia Schools dedicated to preparing students from low-income and underserved communities for college and career. One of the primary structures that has been developed to provide personalized support for students is its advisory system, Possi Circles, representing the Possibilities for students at the U School. These non-academic advisory/support groups of 10-15 students and one faculty leader form during freshman year and remain together for the duration of high school. Research supports the central importance of relationships in helping students, particularly at-risk youth like those at the U School, find success in school and develop lifelong capacities for well-being and achievement. This paper presents a set of recommendations, rooted in the science of positive psychology, for optimizing the form, content, and implementation of Possi Circles, including: a defined pathway to successful Possi Circles with a progression of measurable milestones, additional curriculum for year one Circles, and suggestions for successful implementation.