This quantitative nonexperimental comparative study aimed to evaluate if a difference exists between senior leadership groups at an institution regarding student retention and student satisfaction and if a relationship exists between student satisfaction and retention at a private college in Illinois. Prior research validates the effects of leadership are felt throughout an organization. However, leadership in higher education faces some unique challenges, such as meeting the job market demands and the needs of the many different constituencies. One aspect in which leaders and institutions in higher education are assessed is student retention outcomes. Yet, no magic formula has been discovered to increase an institution's retention rates. To further explore aspects of the students' experience that may affect retention, this study evaluates the following questions regarding one Illinois private college: Does a difference exist between senior leadership groups regarding student satisfaction? Does a relationship exist between student satisfaction and student retention? Does a difference exist between senior leadership groups regarding student retention? Archival data were collected from the college spanning six academic years, including Student Satisfaction Survey results and retention rates. The data were evaluated concerning two different senior leadership teams. However, the results determined there is no statistically significant difference between senior leadership groups regarding student satisfaction, nor was there a relationship between student satisfaction and retention. Additionally, no difference was found between senior leadership groups regarding retention. Therefore, institutions should consider a robust plan addressing more than student satisfaction and senior leadership effectiveness when developing retention plans. [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.]