This article examines how to prepare professional social workers for real-world nonprofit leadership roles. A pilot course assignment that incorporates a quasi-organization fieldwork simulation developed by the author is described. Development and application of critical thinking skills are reviewed, the course objective is explained, and methods and content that evolved during a three-semester trial are outlined. Student assignments and evaluation results indicate that a virtual asynchronous classroom experience is beneficial for students and faculty and that MSW administration students studying advanced generalist practice are an under-recognized potential source of nonprofit leadership.