In the digital world, business executives have a heightened awareness of the strategic importance of information and information management to their companies’ value creation. This presents both leadership opportunities and challenges for CIOs. To prevent the CIO position from being marginalized and to enhance CIOs’ contribution to business value creation, they must move beyond being competent IT utility managers and play an active role in helping their companies build a strong information usage culture. The purpose of this article is to provide a better understanding of the leadership approaches that CIOs and business executives can adopt to improve their companies’ information orientation. Based on our findings from four case studies, we have created a four-quadrant leadership-positioning framework. This framework is constructed from the CIO’s perspective and indicates that a CIO may act as a leader, a follower or a non-player in developing the company’s information orientation to achieve its strategic focus. The article concludes with guidelines that CIOs can use to help position their leadership challenges in introducing or sustaining their companies’ information orientation initiatives and recommends specific leadership approaches depending on CIOs’ particular situations.