Many researchers and practitioners recognize that there is a link between the failures of information system (IS) provision and flawed Information Requirements Definition (IRD). Misinformation arises from defective communication between clients and analysts and lead to situations where the actual requirements of clients are not identified and properly represented in the subsequent information system. Recent research suggests that this could be the result of inquiry methods that do not subscribe to known learning theories and instead focus on contextual factors affecting client learning. In this paper, we explore the underpinning ideas of client-driven requirements definition and attempt to find a way of “navigating” the gap between what the client wants and what the technical expert can provide. The approach described stimulates client learning, which we suggest is a fundamental component of a successful outcome. We propose a method of requirements analysis that has shown its value in helping to overcome the communication gap between client and developer while creating a collaborative learning environment. The lessons learnt from this research may provide an interface for other technology driven development methods.