The role of the chief information officer (CIO) continues to be the subject of much discussion and speculation. Is this just a new name for the MIS manager, or is there truly a new and significantly different function? How has the role of the information systems manager evolved with the changing needs of business? How does the CIO bridge the gap between the organization's strategy and its use of information technology? According to much of the prescriptive literature, bridging this gap is the CIO's definitive function. This article addresses these questions by studying five successful CIOs in five divergent industries. The CIOs were studied using the structured observation methodology employed by Mintzberg in his study of CEOs and by Ives and Olson in their study of MIS managers. The findings suggest that the CIO operates as an executive rather than a functional manager. He or she is an active participant in strategy planning and acts as a bridge between the information technology group, the functional areas, and external entities. This study provides a view of how these difficult tasks are accomplished on a day-to-day basis: through scheduled meetings, interaction outside the information technology unit, a skilled reading of situations, and a strategic focus. Factors affecting the CIO's participation in strategy planning meetings include whether he or she has formal resource allocation authority and their level of peer acceptance. Lessons learned from this research pertain to the delegation of day-to-day tasks, expenditure authority, avoiding adversarial relationships, liaison activities, careful use of language, being perceived as a user of information technology, and the need for quiet time.