Educational leaders have been held increasingly accountable for demonstrating significant gains in student achievement in the wake of education reform policies such as No Child Left Behind. This achievement is often defined as positive gains in attendance and test scores as discipline referrals and suspension numbers decrease. Socioeconomic and cultural contributions to student achievement are often relegated to secondary analyses, are used as deficit explanations when achievement is not increased, or are ignored completely. While this approach may give a snapshot of conditions at a given moment, it does not provide program evaluators with enough information to appropriately assess the implementation of interventions. This qualitative study examines the implementation and evaluation of a prosocial intervention in 10 schools serving American Indian families designed to reflect the culture of program participants and community stakeholders. Findings of the study demonstrate that the relationship between leadership and evaluation participants improved as they worked as partners rather than in isolation. Additionally, gains in prosocial student behavior were observed when traditional evaluation methods were suspended for more culturally appropriate methods that allowed for greater collaboration and timely modifications based on emerging research. (Contains 1 table and 1 figure.)