Recent Requirements Engineering research, recognizes that successful system development relies upon the ability to model and understand the intentional structure of the organizational and business environment within which an IS is intended to operate. The importance of establishing and maintaining explicit links between information systems requirements and business goals is further emphasized by recent research in the areas of business re-engineering, systems evolution and change management.This paper presents our approach for deriving and supporting decisions about system requirements based on the teleological paradigm. In this approach requirements for a new system are seen as the fulfillment or operationalization of organizational and business goals . In contrast to conventional goal-oriented approaches in which requirements are derived by high level goals by a (mostly) top-down goal decomposition process, we perceive goal operationalization as the iterative process of experimenting-in-action, using scenario generation techniques to refine enterprise goals to a level at which they have an operational definition.