The purpose of this study was to investigate the possibility of a relationship between second-order change leadership behaviors of high school administrators and changes in student achievement on the Florida Standards Assessment English Language Arts/Reading component and the Algebra 1 End of Course examination in two large urban school districts. This study further sought to determine the leadership behaviors that high school administrators felt had the most impact on student achievement. As a mixed-method research study (N = 69), quantitative and qualitative data were collected for analyses. Quantitative data were collected via the Principal Actions Survey (PAS) developed by La Cava (2009). A Pearson r correlation was conducted to determine if there was a relationship between individual principal scores on the PAS and changes in student achievement from school years 2016 and 2017. Qualitative data were collected via telephone interviews using the Second-Order Change Principal Interview Protocol (Taylor, 2007). A thematic analysis was utilized to determine themes among administrator responses, specific to the seven leadership responsibilities determined by Marzano, Waters, & McNulty (2005). Themes were determined by frequency of occurrences among interviewees. The quantitative analysis determined that there was no statistically significant relationship among the mean scores of principals on the PAS and changes in student achievement. Qualitative analysis revealed themes specific to administrator change implementation. Themes included: creating a culture of change, data-driven professional learning communities, professional learning, development, and administrator leadership.