Strategic Information Systems Planning (SISP) is an important activity for strategic use of IS/IT in today’s dynamic and increasingly digitalized organisations. However, SISP is not a very straight forward task as it entails simultaneous multiple planning views as well as changing environmental and organisational issues. Although SISP has been widely studied, to date theory on SISP facilitators remain sparse. Therefore the aim of this study is to explore SISP facilitators for sustainable organisational performance and a competitive advantage. This study explores the relationship between SISP facilitators, SISP success and the outcome of SISP in organisations. This study proposes a model indicating the relationship between facilitators of SISP success and organizational outcomes. By surveying a random sample of SISP experts in large South Korean organisations, and via SEM analysis, the relationship between SISP facilitators and outcomes has been determined. The outcome suggests that facilitators positively affect SISP success through improved business-IT strategic alignment and IS planning effectiveness. SISP success includes the achievement of dynamic capabilities and IT infrastructure flexibility. This study proves that a positive relationship among facilitators is essential for SISP and successful organizational outcome. This finding adds to the theory of SISP, and provides a guide to Information Systems planners and organizational managers.