Cyprus education is currently in a reform process part of which is the legal revision allowing private college-standard institutions to transform to private university-standard institutions. This study adjusts the ITPOSMO framework (Heeks, 2001) to estimate potential gaps between the current (college-standard) and the ideal (university-standard) situation of academic institutions across different parameters. The purpose of the study is to assess the overall likelihood for the success of the change intervention and to recognize the role of the leader in the transformational process to close potential gaps and increase the likelihood of success. To achieve the above, the proposed study employs a case study approach (Yin, 2003) focusing on a private college-standard institution in Cyprus. In-depth interviews will be conducted with college personnel who either have the position or knowledge power to be potential leaders in the transitional process (director, course coordinators, heads of departments, and faculty representatives). The proposed study is of great practical significance, due to new dynamics created by the legalized reformation that necessitates college-standard academic institutions to respond. In this transitional period, the study feeds information to college-standard institutions in Cyprus that have either already embarked on the process of changing to private universities, or are planning to do so in the near future. Specifically, the study aims to suggest a roadmap of how to approach the transformation process successfully through effective leadership. Finally, the theoretical significance lies in the resulting customized model that will be applicable to changes in other educational institutions.