The demand for effective leadership within higher education's student affairs sector has never been greater. The overall effectiveness of the student affairs organization may be related to the leadership practices of the chief student affairs officer (CSAO). While theoretical and empirical foundations for leadership styles vary, colleges and universities are investing significant time and resources to find or train qualified CSAOs to successfully lead their student affairs divisions. Effective leadership is synonymous with transformational leadership and personified in five exemplary leadership practices according to James Kouzes and Barry Posner: (a) modeling the way; (b) inspiring a shared vision; (c) challenging the process; (d) enabling others to act; and (e) encouraging the heart. Thus, the question is whether a correlation between these exemplary leadership practices and organizational effectiveness exits. The purpose of this study was to determine any correlation between transformational leadership practices in CSAOs at small, non-profit, bachelor's degree granting colleges in Midwestern states and organizational effectiveness in student affairs. The study was cross-sectional, quantitative, and non-experimental. It used a descriptive-characteristic design as it measured the leadership practices of a target population (CSAOs) and their organizational effectiveness. CSAOs and their respective college/university presidents were invited to participate in this study by completing their respective surveys. Participating CSAOs completed the Leadership Practices Inventory which measured the five exemplary leadership practices. Presidents completed the Student Affairs Organizational Effectiveness survey, which measured their perceptions about organizational effectiveness in their respective student affairs division. Correlation and multiple linear regression analysis were used to look for relationships between leadership styles with organizational effectiveness. The study revealed that none of the leadership practices scores of CSAOs were statistically significant predictors of student affairs organizational effectiveness.