Information Technology (IT) leadership is a domain in need of investigation and development. Here, we present a general model for problem solving leadership and describe our application of that model to IT organizations, with special attention to the role of the Chief Information Officer (CIO). We tested the real-world value of this model through intensive interviews with 26 senior IT executives of major organizations, from which we identified four key leadership challenges facing CIOs today: (1) bridging cognitive gaps; (2) building and managing problem solving diversity; (3) shifting focus to process; and (4) solving problems and managing change. Integrating problem solving concepts with insights gained from the interviews, we offer practical approaches for aligning IT with business objectives, transforming the image of IT, and managing change, among other recommendations.