Strategic Information Systems Planning (SISP) is an important process in the implementation and use of IT systems in today’s dynamic and increasingly digitalized organizations. However, SISP is not a straightforward task, it is a process that covers simultaneous multiple planning issues often in changing environmental and organizational climates. Although SISP has been widely studied, and evaluating the SISP process has matured, theory on SISP facilitators that enable successful outcomes remain sparse. The main objective of this paper is to explore such facilitators and to investigate their relationship and contribution in achieving SISP success. By postal surveying a random sample of managers with SISP experience in South Korean organizations, we modeled the relationship between facilitators of SISP and their outcomes. The study used Structural Equation Modelling to analyze and validate its findings. This study suggests that facilitators positively affect successful SISP through business and IT alignment. It also demonstrates that effective SISP has a positive effect on organizational outcomes by ensuring organizational capabilities and IT infrastructure flexibility. The findings of this study expounding the role of facilitators adds to the theory of SISP and provides a guide to planners and managers responsible for information systems.