Computerized simulation can now play a new, crucial role in the ambiguous real world as a facilitator of communication. One of the most serious problems with which organizations are now confronted is incommensurability, defined roughly as communication breakdown. This is a problem because, to cope with ambiguity, it is essential to share knowledge in the organization. Even when the same natural language is used, commnications within and among the organizations are often extremely difficult, Although there are many articles on examples of how simulation/gaming can improve commnication capacities, most of them are in classroom settings and none have identified the process involved. The purpose of this paper is to present a “middle-rage” theory of communication and simulation/gaming which is applicable to ‘real world’ settings.