Research into young children’s leadership skills is sparse and focuses on leadership in early childhood classroom contexts. Understanding of leadership development in young children can be expanded by studying parents’ perceptions of children’s leadership development as it is enacted in contexts outside of the school. This qualitative study examined beliefs, practices, and contextual relationships of families with young children who were identified by teachers within their schools as having strong leadership skills. Student leaders were identified according to the Leadership subscale of the Scales for Rating the Behavioral Characteristics of Superior Students, 3rd ed. Four mothers and three fathers of identified first graders who met gender and ethnic selection criteria participated. Interviews were conducted with structured and unstructured open-ended questions, and parent journals were collected from participants. Using Bronfenbrenner’s bioecological model of human development as a guide, parental perceptions of contextual influences on young children’s leadership development were investigated. Findings indicate that parents were intentional in trying to develop characteristics and dispositions in their children to help them become good citizens but did not necessarily consider their actions as also building early leadership skills. Information concerning contextual situations, relationships, tools, and characteristics of early leadership development is shared. As parents discussed opportunities for their first graders to develop leadership skills, an unexpected theme emerged regarding benefits of rural living for young leadership development.