IT management processes have been growing as the development of modern IT systems has grown. These are often complex with multiple interdependencies that can make it very difficult for Chief Information Officers (CIOs) to comprehend and be aware of potential risks. These risks have the potential to translate into decision making inefficiencies for an organization. Risk analysis for decision making in the planning and monitoring of these systems can be a complex and demanding task. Intelligent decision making in IT management processes and systems are a crucial element of an organization’s success and its competitive position in the marketplace. This chapter considers the implementation of Fuzzy Cognitive Maps (FCM) to provide facilities to capture and represent complex relationships in an IT management process model. By using FCMs, CIOs can regularly review and improve their IT management processes and provide greater improvement in development, monitoring and maintenance of those processes. CIOs can perform what-if analysis to better understand vulnerabilities of their designed system.