The purpose of this qualitative case study was to explore the decision-making of executives in higher education institutions with an emphasis on information technology (IT) issues. The study explored decision-making through the lens of Descriptive Decision Theory. The three research questions guiding this study were: (1) How do executive skills and abilities support or hinder the achievement of positive technology decisions?; (2) How well do people understand the pros and cons of reporting lines of IT organizations within their institutions?; and (3) How does the IT governance maturity level of organizations shape IT decision-making? Eleven IT leaders (out of a total of 31) were interviewed in a large Midwestern system of colleges and universities. The interview answers and personal notes were triangulated with documents and analyzed using standard inductive coding and content analysis techniques. The data suggests that executive decision-making can be more effective if three recommendations are implemented: one, to implement an effective organization governance structure; two, to ensure the IT leader reports to the highest level, the President; and three, to develop skills in communication, change management, project management, resource management, risk management, operational management and systems thinking. These skills are critical to both the success of the executive and the effectiveness of the decisions made in the organization. The most important implication of this work is that higher education institutions have choices that can ensure their investments in information technology are not wasteful and can lead to better expectations and outcomes. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]