Right hemisphere brain damage (RHD) can cause challenges with information gathering. Cognitive processes aid in implicit and explicit information gathering, yet the relationship between these processes and question-asking, the most explicit avenue of information gathering, has not been explored. The purpose of this exploratory descriptive study was to test the hypothesis that adults with RHD differ from controls in the types of questions produced during a conversational discourse task and whether observed differences are associated with cognitive limitations. Adults with RHD (n = 15) and controls (n = 15) participated in a 5-min "first-encounter conversation" and were assessed for attention, memory, executive functioning (EF), visuospatial skills, and language domains using the Cognitive Linguistic Quick Test (CLQT). Questions produced during the conversation were coded and tallied by type: polar (yes/no), content (wh-), or alternative (A or B) using Computerized Language Analysis programs. Groups were compared on total questions used, use of questions by type, and CLQT domain scores; associations were computed between cognitive domain scores and question types. Compared with controls, adults with RHD used half as many questions overall and scored significantly lower on the attention, executive function, and visuospatial domains of the CLQT. For the RHD group, there was a significant correlation between EF scores and the production of content and polar questions. The frequency of question-asking is important to understanding the communication profile in adults with RHD. Executive function, attention, and, to a lesser extent, visuospatial capabilities may contribute to question-asking behaviors in conversation in this population. The RHD Framework for Asking Questions is proposed to illustrate the potential areas of deficit in the question-asking process after RHD.