Collective impact (CI) initiatives provide a promising collaborative community-based approach for addressing health disparities, but they are challenging to evaluate. This paper provides a detailed strategy for addressing these challenges through a case study, with the goal of not only of evaluating the CI, but also putting organizations in a position to implement and maintain sustainable self-evaluation efforts over time. A three-phase evaluation strategy was developed and implemented via a community-academic partnership to assess the impact of the CI. Process and outcome data from a CI to address health disparities in a Chicago community were collected and analyzed. The evaluation strategy, following the developmental, formative, and summative phases, helped a CI overcome barriers and build capacity for ongoing evaluative work for its members. Considering the flexible, low-technology approach, this strategy is a valuable resource in assisting individuals seeking to create a successful and sustainable CI evaluation.