Leadership is about transformation. It is the opportunity to transform people, places, and possibilities. The purpose of the study reported in this article was to identify means to assess leadership development and performance. Although leadership development and performance can be assessed, school systems often lack consistent methods, frameworks, or efforts to evaluate leaders. This study identified three school administrators and examined assessments that were used to measure leadership development and performance. Sources of data for this study were researcher site observations, field notes, interviews, and leadership performance assessments. The most evident outcome from the study of leadership development and performance was the lack of formal job assessments. A second finding of this study was the lack of performance criteria identified for each leader. A third outcome of the study was the strong personal desire by leaders to identify and measure his or her leadership development and performance. In summary, the study of three transformational leaders reflected a lack of formal performance criteria or assessments to measure leadership. A major implication of this study on transformational leadership development and performance assessment is the need to provide leaders with clear performance criteria and assessment.