IT organizations need to react to changes in the business, the domain (e.g., regulatory issues), and the technological development. While some of these changes can be handled by adopting agile practices, others might have large, irreversible effects on the organization as a whole. While flexibility and agility have found their way into software project methodologies, IT organizations struggle with their adaptation at organizational level. This paper presents preliminary results of a grounded-theory study aimed at understanding how experienced managers handle flexibility. The results are a rich empirical source for improving flexibility of an IT organization at the strategic level and also a good starting point for further research towards generalizing agile ideas beyond software projects.