This chapter introduces the concept of rich picture stories or scenarios to establish a collaborative effort in the design of new information systems. Systems designers need contextual information about their users in order to design and provide information systems that will function effectively and efficiently within those contexts. Story-telling or scenarios allow developers and consumers alike to create that all-important “meeting place” from which comes a collaborative effort in the design of new systems. One of the primary issues inhibiting the further use of storytelling or scenarios in information systems is the issue of validation, which is explored. It is hoped that this chapter will provide insights into the opportunities available to information systems users and designers to improve the quality of information systems through the use of valid user-driven scenarios.