Schools are a critical setting to promote healthy youth development through the provision of evidence-based programs (EBPs), yet preventive EBPs in schools are underutilized. The Exploration, Preparation, Implementation, Sustainment (EPIS) framework highlights numerous factors that may influence program adoption during the Exploration phase and progress monitoring during the Implementation phase. However, no research has systematically and simultaneously identified the factors that influence school administrators' decision-making during these important processes. We conducted semi-structured interviews with 24 school administrators in the Midwestern region of the U.S. to understand how they weigh various considerations that inform their adoption and progress monitoring of prevention programs. Results indicated that school administrators consider five separate factors during the adoption decision, prioritized in the following order: (1) need for the program; (2) school community buy-in; (3) contextual fit; (4) resources; and (5) program characteristics (including the evidence-base). Further, administrators consider five indicators to monitor program performance, prioritized as follows: (1) intervention fidelity; (2) quantitative and qualitative data that determine if the identified need was met; (3) school community buy-in; (4) resource consumption; and (5) program characteristics. Implications for prevention scientists and suggestions for future research are discussed.