This study was designed to investigate the perceived experiences encountered by principals in the state of Illinois regarding professional development sessions offered through the Illinois Administrator Academy. The fundamental value of the Illinois Administrator Academy was designed as one of 169 specific initiatives in association with the passage of the omnibus education act of 1985. The administrative oversight component of this critical piece of legislation was responsible for assuring that Illinois principals were indeed continuing their education and honing their skills as instructional leaders for students within their charge. Two dimensions of principal professional development offering through the academy were assessed to determine: (a) if trainings maximized upon learning experiences deemed coherent across an assorted framework for delivery, and (b) if the content of the trainings experienced aligned with skills demonstrated by research to increase student achievement. The research aligned within this study utilized both the Structures of Training and Process of Implementation (STPI) model as an analytic construct for determining placement of professional development offering within a fourfold typology, as well as the 21 Leadership Responsibilities demonstrated by the McREL group to be positively correlated to increased student achievement. The study was conducted through a series of three phases employing both quantitative and qualitative methodology. In Phases I and II of this study, methods of quantitative statistical analysis utilizing random sampling technique were developed to narrow the population group of Illinois principals from 3,788 subjects to a subgroup of nine. This population group was provided by the Illinois State Board of Education (ISBE) and entailed descriptive statistical data per participant based on records collected from the Education Certification System (ECS). In Phase III, the researcher conducted on-site visits to the school for the purpose of interviewing and collecting documents pertaining to Illinois Administrator Academy experience. Pattern codes were used to analyze the data with general themes and interpretation by participants noted. The prominence of academy experience by the Experienced Principal Participant subgroup was compared by elements of process and content to the STPI model, as well as 21 Leadership Responsibilities offered by the McREL research. In addition, the researcher collected and interpreted responses by subgroup participants to make recommendations for future studies and the related field. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]