Abstract: Sketch recognition can capture the sketching component of a multimodal conversation about design, but it does not capture information conveyed in the other modalities. The informal speech that accompanies a sketch often has a considerable amount of additional information. We want to develop a digital whiteboard capable of understanding both sketching and speech, and capable of participating in a conversation similar to one that the user would have with a human design partner. We conducted a user study to help us understand what kinds of conversations users would have with a whiteboard capable of recognizing a sketch. We report results that we believe will help guide the design of an effective multimodal interface, and discuss implications for system architectures.