The importance of information technology (IT) and quality of leadership to business are widely acknowledged in both academic and praxis literature alike. The need for top management involvement in the strategic management of IS/IT for competitive advantage has been a recurring theme, with increasing vigour since the en masse creation of Chief Information Officer (CIO) positions in private and public sector organisations. Previous research has suggested that IS/IT adoption implies organisational innovation and as such there is a need for senior executive involvement. This chapter 1 presents an exploratory framework that links the quality of the leadership to the effective adoption of new IS/IT in organisations. The chapter also explores the demographic influence on leadership philosophy. Data from senior managers and executives in the Australian Public Service (APS) shows how different aspects of leadership philosophies influence (positively and negatively) four integral facets of IS/IT adoption - IS/IT Training, IS/IT Deployment, IS/IT Skills, and IS/IT Impact on the Organisation.