This chapter reports on an e-Learning readiness study that was supported by Kuwait Foundation for Advancement of Sciences (KFAS) under project number (2013-11109-05) and carried out to assess the organizational and individual factors of the two major stakeholder groups (teachers and students) in the secondary education institutions to provide significant information to the policy makers and regulatory bodies for the development of successful e-Learning strategies. The chapter looks specifically at some factors at the initial stage of an e-Learning introduction that can have tremendous impact on the later stages of the process. Later on this chapter, discussion and suggestions are presented to be instrumental in implementing successful eLearning strategies for many countries, specifically Kuwait, and will also benefit e-Learning initiatives in similar institutions in other Gulf Cooperation Council (GCC) and beyond.