The purpose of this study was to examine the descriptions college presidents use and the stories they tell about the students in their institutions when communicating with certain influential stakeholders, such as trustees, alumni, and funders. The researcher examined themes and patterns in the portrayal of students through these stories to see if a composite emerged of what the 21st century student might look like through the college presidents' perspectives. The study highlighted the research from the presidential viewpoint, as to how and for what purpose they incorporate student descriptions in their discourse. In studying the communication of a college president with certain stakeholders, a broader understanding of the organizational identity comes through as "embedded" within different membership and meanings (Scott & Lane, 2000). Nine college presidents from the City University of New York participated in open-ended interviews. These interviews were then analyzed using Mayring's (2000) Inductive Category Model. Findings from the study led to four major conclusions. The "mentor narrative," although dominant throughout the interviews, was absent from communication with the stakeholders and there were important untold stories. The second finding was the tension and duality experienced by the presidents and how this influenced their choices in their role as liaison between the stakeholders and the university. The third finding was the "diversity paradigm." This study revealed the newer and multifaceted layers of diversity and how this paradigm is different from the historic understanding of diversity in the undergraduate student body. The last finding was the shift in the American Dream narrative and the implications of that shift for CUNY and for higher education nationwide. This study has value for leaders within a higher education environment that is rapidly changing as they can recognize (a) the ways in which they shape discourse in relation to stakeholders as an audience and (b) the influence this shaping has on understanding the organizational culture of their institution and the undergraduate student's experience. [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.]