This chapter provides insight into the challenges faced by independent evaluators working in community settings. Communities are complex, requiring the independent evaluator, who chooses to work in them, to possess a unique set of personal qualities and professional competencies. Social problems are complex and community members and organizations must be engaged for interventions and evaluations to be effective. The authors delve into the evaluators' professional competencies applicable to working with communities and the perspectives required to help communities evaluate their social change strategies. The authors discuss the necessity to demonstrate cultural humility and cross-cultural competence, a commitment to justice and equity, an ecological perspective, empowerment, community inclusion, and knowledge of program development and implementation strategies typical in communityoriented work. This chapter suggests guidelines and resources to assist the evaluator working in communities. It concludes with examples of results from the authors' work as independent evaluation consultants working with community coalitions.