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Prior studies as well as the present study indicate that improvisation in leadership decision-making transpires in organizations 75-90% of the time. However, little research has explored the development of this skill-set in educational leaders. The purpose of this study was to assess the effects of a new workshop applying a Holistic Improvisational Leadership Model on educational leaders in four sites across the country. Primary findings revealed that educational leaders gained better listening skills, noted an enhanced sense of mindfulness of others’ actions and their influence on others, and improved their ability to collaborate with other leaders and their staff. Furthermore, educational leaders perceived that the workshop brought their stress level down to an optimal working level.