This article presents how character development practitioners, researchers, and funders might think about evaluation, how evaluation fits into their work, and what needs to happen in order to sustain evaluative practices. A broader view of evaluation is presented whereby evaluation is not just seen as something that is applied at a program level, but as an endeavor that considers the ecologies and systems within which programs are embedded. The evaluation landscape for youth-serving and character building programs is considered. Strategies for enhancing evaluation practices at the organizational (macro) level are addressed as well as strategies for enhancing evaluation practice at the program (micro) level. Organizational level strategies include deliberate efforts to engage in evaluation capacity building and cultivating evaluative thinking. We also discuss the role of evaluation policy and the need to consider program ecosystems through portfolio analysis. The program level strategies focus on using the Systems Evaluation Protocol to articulate and assess program theories of change.