In the present chapter, we focus on interpreter-mediated business negotiations as simulated in a classroom environment. Drawing on our own experience as dialogue interpreter instructors and on relevant literature, we argue that the structured role-play is a valuable teaching and learning tool to introduce students to the practice of dialogue interpreting in business settings. If the various steps of the role-playing activity are carefully designed and grounded on a dialogic approach, the activity can in fact shed light on the constraints and expectations associated with (interpreted) business negotiations and raise students’ awareness of the coordinating role of the interpreter therein.