Abstract This chapter examines nudging questions as devices for prompting courses of action in multinational Military Observer training. Nudging questions are a way to handle the complexity that associates with the interlocutors’ asymmetric experience and competence and the “role of being more experienced” in relation to other operative roles within the trainee teams. They are emergent and uniquely designed for the situated interactional trajectory and its relation to concurrent activities and change over the interactional episodes. Military discourse and learning in military settings are not built on imperatives, but courses of action can be initiated and progressed also by using softer means. The findings contribute to our understanding of how roles and responsibilities are negotiated and how intersubjectivity and deontic symmetry–or asymmetry–are maintained in collaborative situations.