A principal's leadership is a key part to the success of a school as their leadership guides both instructional and organizational outcomes. Teachers often work beyond their formal duties to see that all their students have their needs met. This is referred to as an Organizational Citizenship Behavior (i.e., when followers display behaviors that benefit the organization or its members beyond their current job requirements). This study investigated the relationship between principal's transformational leadership and teachers' Organizational Citizenship Behaviors and related motivating factors. Participants from a suburban school district completed a questionnaire based on their perceptions of their principal's leadership characteristics and reflections upon their own practices. The results showed the strongest transformational leadership practice is individualized support. This practice demonstrated positive relationships with Organizational Citizenship Behavior, Organizational Concern, and Prosocial Values. The outcomes of this study are intended to assist school leaders in promoting sound citizenship behaviors through leadership practices as well as informing leadership preparation.