This study used a quantitative research approach to attempt to answer the stated research questions. This study focused on two school districts in the State of Wisconsin that have superintendents who had been in their current position between 1 and 6 years. The superintendents had been externally identified as having been effective at building positive relationships within their community. Quantitative data were collected through a survey of the school board members, administrative cabinet members, and union leadership who work with the superintendent as well Chamber of Commerce members from the community. Through comprehensive data analysis, themes were identified and behaviors emerged as being effective at building positive relationships. This study contributes to the current research by identifying leadership characteristics that are effective in creating relationships with the school board, community, union leadership, and the district leadership team. Secondly, it aids superintendents by identifying if their personal perceptions of their behaviors are in alignment with the perceptions of the stakeholder groups within their community. Further, the study identifies which traits are perceived as most beneficial by each of these stakeholder groups. This informs leaders working toward effective relationships as they choose strategies for interactions.