The chapter explores critical roles of internal evaluators in contemporary organizational settings. The need is highlighted for an expanded, reconfigured, unorthodox set of roles and styles of work to meet the needs of the emerging learning organizations effectively. A discussion of major categories of internal evaluator roles emerged from the analysis of the evaluation literature and other sources suggests new directions for how internal evaluation is conceptualized and practiced. Systematic promoting and advancing positive change, evaluation capacity building, decision making, learning, and evaluative thinking in organizations are seen as part of the harmonized internal evaluator role. © Wiley Periodicals, Inc., and the American Evaluation Association.