This paper examines the nature of e-commerce systems development and finds that e-commerce is different requiring a high degree of business innovation and responsiveness. A study undertaken on a B-B e-marketplace in Egypt illustrates the problems with the use of traditional analysis and design techniques. They reduce imagination and the ability to respond to change, as they are systematic, comprehensive and plan-driven. The study focuses attention on the importance of modeling value-added services beside businesses processes for e-commerce applications, as well as the need for self-organizing, non-prescriptive activities, which we call the ?Practice?, that enhances creative thinking and self-reflection on the problem situation. As a response to these findings an ?upfront requirements modeling and design practice? is identified, outlined, and experimented with. It is based on brainstorming sessions guided by the use of a ?non-prescriptive? requirements modeling tool that provides a classification of the possible different e-commerce issues. The introduced tool (the e-Business Issues Roadmap) helps to trigger issues and design ideas. The results found a number of business innovative ideas that were unlikely to have been generated by traditional analysis models.