The purpose of this study was to analyze the relationship between administrator leadership styles and their impact on student achievement. The goal of this quantitative, non-experimental study was to investigate the correlation between administrator leadership styles and third and fourth grade math, Tennessee Comprehensive Assessment Program (TCAP) scores. Math scores were measured by the TCAP which is considered both a valid and reliable measure of proficiency in Tennessee. Third grade student math scores from 2007-2008 and fourth grade math scores of those same students from 2008-2009 were utilized for the mean gain scores. The sample population consisted of seven elementary, Title I school administrators in a middle Tennessee school district. Those seven administrators completed the Leadership Effectiveness and Adaptability Description Instrument (LEAD) which is published by the Center or Leadership Studies and the Myers-Briggs Type Indicator (MBTI) which is published by the Consulting Psychologists Press. The results of this study indicate that it is not necessarily the leadership style of an administrator that effects student achievement or the personality style of the administrator, rather it is the combination of an administrator's leadership style and his/her personality that appears to be most closely related to student achievement.