Paradoxically, although question asking is a fundamental human activity, we frequently ask and answer questions without considering the processes we use. This paper describes two studies that ask “questions about questions,” in order to improve understanding of the often implicit processes involved in the asking and answering of questions, and to inform the design of social tools to aid knowledge workers in asking and answering questions. The first study, using a focus group methodology, led to the identification of thirteen dimensions that can be used to distinguish questions, and the development of an iterative model describing the often surprisingly complex question-asking behavior. The second study extended the findings of the first study by analyzing usage data from an enterprise social networking application to provide insight about how questions are asked and answered using that tool. These analyses revealed significant differences in conversation patterns between question and non-question discussions in the tool. Implications for the design of social question and answer (Q&A) applications arising from the findings of these studies are presented. © 2013 Alcatel-Lucent.