This paper examines the use of cultural probes as a method for fostering collaboration within groups of diverse experts working on creative projects. Using two case examples, we show that probes-short, oblique, and at times whimsical sets of activity prompts-have boundary object properties that can jumpstart interdisciplinary and cross-functional exchange. The first case explores how social scientists and designers used a smartphone-based scavenger hunt activity to gather insights for a workshop on organizational innovation. The second case examines how artist/scientist pairs utilized probe-like prompts to develop short performances for an arts festival. Drawing together theoretical views on boundary objects and cultural probes, we suggest that designed experiences such as probes can create opportunities for both boundary work and the establishment of common ground, which is increasingly vital in the highly collaborative contexts that define work today.