Late in the 19th century, American communities were in a state of flux. As northern abolitionists fought against slavery, relationships among diverse members of society rapidly changed, forcing historical figures to adopt new leadership strategies. Like communities of the pre- and post-Civil War era, modern educational contexts reveal growing diversity (immigration) and rapid societal change (emergence of a large adult learner population and changes in communication), suggesting that analogous leadership skills may be needed to navigate diverse ethnic and social circles. The purpose of this study was to examine historical traits and behaviors conducive to leadership of diverse populations. Due to tremendous success in assisting runaway slaves, as well as service in a variety of capacities (conductor of the underground railroad, nurse, career trainer, and military captain), Harriet Tubman was deemed an ideal candidate for examination. Her experiences and behaviors were analyzed in detail, resulting in a number of recommendations for leadership training and governance of today's American schools.