In this paper we explore the subject of question asking as an inherent driver of enterprise modelling sessions, within the narrower context of the ‘dialogue game’ approach to collaborative modelling. We explain the context, but mostly report on matters directly concerning question asking and answer pre-structuring as a central issue in an ongoing effort aiming for the practice-oriented development of a series of dialogue games for collaborative modelling. We believe that our findings can be relevant and helpful to anyone concerned with planning, executing or facilitating collaborative modelling sessions, in particular when involving stakeholders untrained in systems thinking and modelling.