Abstract: This exploratory study (a) assessed the political skill of superintendents in the Commonwealth of Virginia and (b) identified influences on the development of political skill as related by those in the position. Bolman and Deal (2013), in their research on leadership, viewed the concept through four frames. This study focused on the political frame, viewing organizations as arenas, contests, or jungles with stakeholders competing for power or scarce resources (Bolman & Deal, 2013). In this frame, solutions arise from political skill and acumen, and therefore certain leadership skills are necessary. Study data were collected through an electronic survey sent to the population of 132 Virginia Superintendents. The survey included the 18 items of the Political Skill Inventory (PSI; Ferris et al., 2005). The inventory includes four critical facets, each measuring a key dimension of political skill. Also included in the survey were demographic questions and questions related to factors that influenced development of political skill. Findings indicated that superintendents in the Commonwealth of Virginia collectively self-rate as possessing an elevated level of political skill with a mean of 6.16, only slightly less than the maximum of 7. The only statistically significant correlation (r = .24, p = .029) was found between gender and political skill noting that females tended to score themselves higher than males did. In an effort to further explore, influences were examined, and results indicated that participants\' political skill was influenced by a variety of factors, but mainly by previous professional experiences, personal role models, and professional mentors. This exploration may bring more attention to this specific skill for those who currently hold the position to improve the skill as needed, those who aspire to the position, school boards hiring new leaders for their divisions, and higher education institutions offering pre-service preparation programs or professional development for superintendents. As the position of superintendent evolves to become more complex, far-reaching, and demanding (Kowalski, 2006), so should the examination of those skills required for the role.