Chief information managers (CIOs) lead IT organizations in a changing and uncertain competitive environment. IT managers deal with external environmental changes, changing internal customer needs, and rapid technology changes. Studies suggest that to manage change and prepare for uncertainty, IT leaders should create an organization that is more flexible. The authors propose in this conceptual paper that flexibility can be analyzed and introduced systematically within the IT organization. The authors suggest that three distinct organizational characteristics, anticipation, agility, and adaptability, be combined into a unique ‘IT Flexibility Framework (IFF).’ CIOs could use this IFF to assess the IT organization’s readiness for change and improve its capability to support the agile enterprise. On-going research is planned to validate the IFF and its potential usefulness to manage IT change and uncertainty, while still providing cost-effective and reliable services.