This pilot study investigated the relationship between principal preparation program (PPP) field experience structure and principal instructional leadership preparedness as measured by state certification exams and state-wide student assessment results. The researchers sought to determine if a statistically significant difference existed in principal certification examination scores between principals who completed part-time practicums while maintaining their classroom teaching duties and principals who completed a year-long, full-time internship as part of their PPP. Further, the researchers sought to determine the impact on school-wide student achievement scores for both groups of principals during their first year in a principalship. Findings indicated a statistically significant difference in median state leadership licensure examination scores between the two groups, with internship principals (IP) scoring significantly higher than practicum principals (PP). Other findings indicated, both, PPs and IPs positively impacted SA levels in their first year as principal with schools led by PPs making higher gains in school-wide student achievement scores and schools led by IPs meeting school-wide growth, as measured by the state accountability model, at a higher rate. These findings may aid key constituents in re-envisioning the structure of their current field experiences and re-examining preparation practices to explore innovative methods to prepare school leaders who are trained for the complexity of today's principal role.