Educational leadership preparation programs are expected to train graduates who change their practice and produce outcomes for teachers and students. However, programs are challenged to produce evidence of their impact while also evaluating for formative purposes. This paper describes collaboration between an educational leadership program director and a program evaluator to construct an evaluation system that incorporated program theory, processes, and outcomes. The leadership preparation program, grounded in ethical leadership practices, had a unique design with core tenets that informed choices about the evaluation design. Decisions about data sources were informed by evaluation foci, the availability of existing data sources, and resource constraints. The complexity of the evaluation design paralleled the complexity of the program itself. Leadership content expertise, evaluation design expertise, and genuine collaboration were all essential to the successful design of this evaluation plan. Several recommendations are offered for others collaborating to design evaluations of their programs. (Contains 2 figures and 1 table.)