This article investigates question mapping as a methodology for making sense of the complex issues discussed at a West Coast nonprofit leadership summit in the economic downturn following the terrorist attacks on September 11, 2001. A real-time organizational development tool was employed retrospectively to help frame the fundamental questions raised by the region's leaders about community needs and the sector's role in meeting them. Following a brief description of the summit, the methodology is presented. We then consider how this approach differs from other frameworks for encouraging and analyzing discourse and how it was adapted. The technique is both a heuristic device and a guide with potential for synthesizing community issues in real time or retrospectively. The categorization schema provides a framework for deliberative dialogue and action as well as many potential nonprofit research agendas for the coming years.