The need for top management involvement in the exploitation of information technology (IT) is a recurring theme of information management. Previous research has suggested that this involvement is linked, with a two-way relationship between CEO and CIO. This paper reports on an exploratory research study that set out to identify the determinants of a successful two-way relationship. CEOs and CIOs were interviewed indepth in 14 large organizations based in the United Kingdom. This paper describes an explanatory framework that links the quality of the CEO/CIO relationship to identified attributes of each of the parties, and of their host organization. Successful relationships seem to be linked to a shared vision of the role of IT as an agent of transformation. The CIOs in these successful relationships may have extensive IT backgrounds, but they are accepted into the top management team and are seen to contribute beyond their functional responsibilities.