Improving leadership development opportunities among those likely to ascend to the principalship is a particularly effective policy response to reform advocates. But the school district level requires a deeper understanding of the individual personality preferences and leadership styles of those preparing to apply for the next round of principalships, namely assistant principals. Educational decision makers, particularly superintendents, must move away from interview intuition, employment networks, and formal credentialing toward a more data-based matching of personalities and styles with position requirements. This article explores the personality preferences and leadership styles of aspiring school principals, including differences in race, gender, grade level, and school district location. It uses data gathered through assessment programs for aspiring leaders conducted in two large South Carolina school districts during fall 2006. Two personality inventories and two leadership assessments provided the dependent variables. The group profile of assistant principals that emerged from these personality inventories and leadership assessments provides several insights into the personality preferences and leadership styles of those aspiring to the principalship in South Carolina and possibly in other states as well. This profile data also has important implications for those involved in university and school district pre-service preparation and early career development of school leaders. (Contains 1 figure.)