Information technology has the potential to change community college administration procedures; merging technological knowledge and business skill; creating a need for further definition and understanding of current Chief Information Officer (CIO) position. However, the existing research on this topic focuses on the merging leadership roles and interactions in business and is limited in identifying phenomena characteristics that lead to a positive strategic alignment. Accordingly, the purpose of this qualitative embedded multiple case study was to explore Institutional Management Team (IMT) and CIO perspectives about CIO's inclusion in leadership decisions in community college settings. The study population is community college leadership including Presidents, Vice Presidents and Chief Information Officers. The sample was comprised of three IMTs and three CIOs from six different community colleges in western New York. Individual, qualitative interviews were conducted with the six study participants, facilitated by an interview guide. Data were transcribed and analyzed to address the study research questions and provide information about leadership decisions in community college settings. The findings indicated communication is the most important part of the IMT/CIO dyad, CIOs consider the top down management style of the IMT and lack of inclusion by the IMT are barriers to the inclusion in leadership decisions by the IMT, and top down management styles are a large barrier in CIO inclusion in the decision making process of an institution and communications was the force to address the lack of inclusion brought about from the top down management style and the lack of inclusion. The results of the study provided information to impact future directions of community college management techniques. Future research includes expanding the study beyond the state of New York and a deeper investigation of the reporting structure and existing dyad compared to various outcome measures of technology in the institution. [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.]