Management's dilemma, when allocating financial resources towards the improvement of technological readiness and IT flexibility within their organizations, is to control financial risk and maximize IT effectiveness. Technological readiness is people's propensity to embrace and use technology. Its drivers are optimism, innovativeness, discomfort, and insecurity. Together, these drivers create the motivations for employees, management, and customers to use technology to achieve competitive advantage. IT flexibility is associated with acquiring networking hardware that would improve IT connectivity, modularity, and compatibility within the organization's IT infrastructure. By prioritizing the constructs of technological readiness and IT flexibility towards IT effectiveness, management would know when and where to allocate their corporate resources. This study's findings provided statistical evidence that the combination of the interaction term of technological readiness and IT flexibility (TRxITF) did have a more positive relationship than the individual relationships of these independent variables on IT effectiveness. The implications are that managers should allocate financial resources equally among technological readiness and IT flexibility in their organization. It is recommended that this study be extend into educational departments in large companies. These educational departments would have knowledge on the effectiveness of employee training and employee preparations that would facilitate the acceptance and use of technology within their organizations. In addition, IT flexibility research could be expanded to include small and medium organizations in an effort to validate and generalize this study's findings on the positive relationships among IT flexibility and IT effectiveness. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]