The present study explored the applicable situational leadership styles of experienced military managers attending an advanced leadership educational program. While attending this program, these managers were requested to reveal the results of their situational leadership self-assessment in which they participated. A total of 620 managers agreed to reveal their results, and descriptive statistics were conducted to determine the findings of their situational leadership self-assessments. The study research results revealed two situational leadership styles were predominating: (Telling and Participating). The findings of research study have significant implications for managers when leading individuals and teams for organizational success. These findings also may contribute to better understanding of the situational leadership styles which characterize managers when leading people and team members. Additionally, the findings of this study also have implications for teaching situational leadership skills in a variety of settings to include educational leadership programs such as the one reported here.