Many challenges face CIOs in their management of IT systems; yet, very little research is available regarding the issues and constraints associated with their role. CIO leadership is still a subject of inquiry for those with aspirations to pursue such a position. The specific problem of the current qualitative phenomenological study concerned the absence of best practices and standards for interviewing and selecting prospective CIOs. A group of 20 participants, who represented a cross-section of executives currently working throughout the United States or have experience as participants in the CIO interview and selection process or currently serving in the CIO position, were included in the study. Three themes emerged from the study; based on the participants' responses, the phenomenon persisted because there was (a) the inability to determine the experience needed to support the CIO position; (b) gaps in understanding the leadership skills needed to support the CIO position; and (c) the lack of effective strategies to support the sustainability of the CIO position through succession planning. "A Circular Flow Model for Improving the Selection of CIO Candidates" emerged as a foundation to assist decision-makers in reevaluating and restructuring their organization's recruiting and interview practices and objectives for prospective CIOs. [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.]