How have presidential leadership strategy, decision approaches, and institutional culture preferences influenced fund-raising effectiveness at a historically Black college for women? These conceptual dimensions guided a qualitative study that interviewed three recent Spelman College presidents and investigated documentary evidence to develop an understanding of each president's relative successes. Although generalizability is not possible when studying a single institution, the three very individualistic approaches to fund-raising adopted by these presidents indicate the contextual nature of fund-raising effectiveness and highlight the need for knowledgeable institutional planners who understand each of these conceptual dimensions to accommodate the varying contexts of their institutions. (Contains 2 figures.)