Despite a long interest in Information Systems (IS) development, the need to improve the success rates of IS projects remains relevant. Continuing disappointment with project performance has led to suggestions that a broadening of the project management (PM) conceptual base could bring new insights to this enduring problem. Consequently, this study acknowledges the sociological nature of IS projects and will explore the dynamic interaction of culture and leadership to expose better explanations for project performance. This interpretive study will use the Cultural Dynamics Model (CDM) as a theoretical lens, and will privilege a view of ‘data as text’ over ‘data as fact’ by accentuating reflexivity in the research. Four IS projects in two organizations will serve as cases in a multiple case study approach. This paper argues for a dynamic, reflexive study of culture and leadership and positions the CDM as an appropriate theoretical framework to support this approach.