Information Systems research has investigated what roles CIOs should play but has paid very little attention to when these executives are more likely to be effective in their various roles. This paper focuses on the role of change agent, and proposes a three-stage model (“Conquest,” “Exploration,” and “Settlement”) describing what combinations of change agentry models CIOs follow during their time in office. The model suggests that CIOs predominantly follow the “advocate” model of change agentry at the beginning of their tenure, and combine both the “advocate” and “facilitator” models as they progress in their position. As they reach the end of their tenure, CIOs mainly adhere to a balanced combination of “facilitator” and “traditionalist” roles. The combinations of change agentry models CIOs tend to follow are explained by the patterns of evolution of five key characteristics: commitment to a paradigm, task knowledge, information diversity, task interest, and power and influence.