There is a disconnect between information technology (IT) and information systems (IS) that lies at the foundation of frequent failure in cost, schedule, and/or performance of IT/IS. This disconnect can perhaps be reconciled through a focus on the socially constructed and emergent nature of IT as it enters and is used by an organization. The argument is that IT investment is not working with the right knowledge for evaluation and justification and does not reflect human nature in decision-making. The hypothesis is that a structured dialog technique, by focusing on properly perceiving human felt needs rather than exclusively technological aims, improves the process of IT project evaluation and justification. This breaks the requirements development process into multiple, time-efficient steps in order to properly acquire and convert tacit knowledge into explicit and then embedded knowledge. The research questions include: What are the foundations of IT/IS failure, and how do they relate to the absence or presence of structured dialog? What are the dimensions of structured dialog that help fulfill the gap between users' felt needs and IT specifications? Finally, what are the aspects of tools and methods applied in early investment lifecycle activities that can, or seem to, fulfill these dimensions? This study posits a conceptual decision framework using structured dialog to perhaps prevent IT failure. The research starts with an analysis of IT/IS failure factors using a metaevaluation approach tailored for qualitative, interpretive analysis as a metainterpretation with respect to IT case studies and a synthesis of those factors. Then, a pilot of a survey approach is performed to profile and test elements of structured dialog and associated early lifecycle tools with the business/mission process community and technologists. This is then made practical by creating a conceptual decision framework for management to use in framing complex investment decisions such as IT investment. The framework includes obtaining early clarification of the purpose of the new IT/IS system, improving team dynamics to enable better collaboration, making a specific, shared decision as the basis of collaboration, and focusing on structured dialog. The elements of structured dialog found to underlie this decision framework are the production and use of shared meaning, creation and use of common language, repetition and continuation of dialog, and facilitation of shared experience. These elements achieve an organizational epistemology, or knowledge framework, that can potentially facilitate more accurate acquisition and development of IT (that is, the system-as-created), and perhaps lay the foundation for subsequent transition into IS (that is, the system-as-used) that an organization should use in the manner needed and intended. In addition, this epistemology underlies the process, and products, of successful IT/IS architecture. [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.]