Rapid advances in information technology(IT) and telecommunication systems impact the number and quality of decision-making in organizations. Specifically, middle mangers must posses or develop the creativity necessary for survival in a constantly changing and volatile business environment. While tradition and conventional wisdom tell us that a middle managers role centers on control and monitoring, todays competitive arena has spun out a new managerial requirement developing and maintaining an innovative attitude. Problematically, most previous research has focused on the issue of changing decision authority (i. e. centralization/decentralization). Moreover, much previous research has also largely ignored environmental changes exposing new roles that middle managers have assumed. This study explores the means of identifying middle managerial roles, managerial possibilities involving the growing popularity of open systems through electronic brainstorming, and an adaptation and development of Diffusion Theory and attempt to counter criticism leveled at the theory's inability to provide an adequate explanation for diffusion of complex organizational technology. This paper develops three ideas: 1) Introducing the 'Chasing Curve' as a theoretical background. 2) Suggesting a new methodology using electronic brainstorming for analyzing the gap between Knowing (the perceived importance of middle managers' roles) and Doing (the degree of current status of middle managers' roles), which we term the 'Spiral Gap Analysis Model'. 3) Identifying a feedback system for minimizing the Knowing - Doing gap, aimed at development of IT strategic priority decision support, which we call this the 'Star Process'.