The Strategic Information System Planning (SISP) is thought to be the first step toward implementing information systems. The development and implementation of a highly aligned information systems still a top concern among academics and professionals, where IT considered as a strategic asset capable of adding value to overall organisation effectiveness. Based on the contingency theory of information system, this paper tend to examine the affect of different leadership styles on the SISP process stages of growth, using the competing value framework (CVF) as a measurement model of leadership orientations, and building on Grover and Segars (2005) measurement model of SISP process stages of growth and contributing to his model by adding a new SISP decision process dimension, lapelled “Intuition” as one of the SISP process stages of growth where it can be seen as the first stage towards the SISP process rationality stage. By linking these two measures one should be able to identify a pattern in which leadership orientation is most represented in each stage of SISP process growth. This paper is representing a theoretical base for empirical testing yet to be carried out.