The purpose of this research was to explore the content and process of nonprofit self-assessment. This paper explores issues around the following question: what does the process of self-assessment look like in urban American nonprofit agencies? The first component of the research was a review of the literature that revealed that organizational assessment is a tool that has not yet found its place in the body of best practices propagated for nonprofit management. Two assessment models were analyzed and compared: The Self Assessment Tool by the Drucker Foundation and the Organics General Program Model created by the Organics team. An author/ facilitator of each model was interviewed about their model and their experiences in utilizing it. It was found that both tools are effective in helping agencies gain a realistic picture of themselves. They are especially helpful to agencies engaged in a planning process. However, the Drucker model is more suited to organizations willing to embrace business sector language and management styles while the Organics model is more suited to more "soft" management styles. A case study of a small nonprofit in Denver, Colorado (USA) explored the process of assessment in action. The case study supported the findings from the first two research components concerning the general lack of awareness and consequently acceptance of assessment as a best practice. There were several significant lessons for managers. Organizational assessment that includes a review of both operational and programmatic components of agency health can help managers gain a more accurate and complete picture of their agency. This insight can especially enhance planning. Both informal and formal assessments were discussed, benefits and limitations of programmatic or operational assessments were also discussed. Perceptions, motivations, and possible implications for managers are discussed as well as an analysis of what comprises a strong assessment tool for use in nonprofit organizations.