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There is an increasing interest in the area of information technology success research within the organizations and academia. The information wave is sweeping around the world and information technology is advancing at breathe taking pace. There is a widespread agreement that leadership has important effects on IT acceptance and use, but little empirical research to date has explored this phenomenon in detail. The way IT is managed and used is very much a product of the culture and management style of the organization. Culture is an important factor in successful technology implementation, innovation, and use. It is the domain that enables or obstructs the growth of the organization. Whereas effective leadership fosters organizational culture conducive to long term IT success. Evaluation of IT effectiveness would help in identifying the right mix of leadership and culture required in the organization. The primary objective of this study is to review the studies related to the relationship between leadership, transformational leadership in particular and IT effectiveness focusing on the role of organizational culture in this relationship. Past literature suggests that there exist a strong linkage not only between leadership and culture but also between IT success and leadership. Organizations having different combinations of leadership and organizational culture have different levels of IT effectiveness. The theoretical contributions and managerial implications are discussed.