This paper is intended to propose a conceptual model that will help researchers and practitioners better understand the importance of individual differences in judgment and decision making (JDM) styles of IT leadership. Additionally, such individual differences in JDM can further help understand how they influence the strategic use of IT resources and their contribution to firm performance and competitive advantage. This proposed conceptual model and future related studies will contribute to existing resource-based view (RBV), IS strategy, and IS behavioral research literature.