Strategic Information Systems Planning (SISP) has been recognized as one of the most essential tasks for better management and supporting strategic use of IS/IT in the current dynamic and increasingly digitalized environments. However, undertaking SISP is difficult, because organisations need to take multiple planning perspectives, including managerial, environmental and organisational perspectives all at the same time. To achieve and sustain organisational performance and competitive advantage, various facilitators affecting successful undertaking of SISP process, and the relationship regarding the facilitators and SISP success, need to be well identified and understood. The relevant SISP facilitators are selected to enhance SISP success and to improve dynamic capabilities. This paper proposes a model to show the relationship between six critical facilitators and SISP success. This research intends to undertake the survey of top 1,000 Korean large organisations to examine the relationships and test the proposed research hypothesis. A pilot study was carried out to confirm the adequacy and reliability of the research instrument, which final items are presented in this paper.