Preparing organizations and assessing their readiness to implement enterprise systems is a growing agenda in information systems research. This chapter examines the challenges that face the preparation of organizations’ stakeholders in managing and supporting the implementation and using enterprise systems in an Arabian Gulf context. The chapter points out the major issues that have been identified by enterprise systems’ professionals such as: lack of business and IT strategies, continuous top management support, insufficient training, inefficient communication procedures, inefficient change management and cultural barriers. To overcome these challenges, the chapter suggests that the preparation should not be limited to end users since the preparation of other stakeholders, such as top managers, project manager and project teams, is essential to successfully implement and use the enterprise system. Based on insights gained by empirical research with enterprise systems professionals, the chapter recommends a number of factors that need to be considered. These have been grouped into the categories of: organizational, managerial, technical, external, and human/social factors.