In 2006, The Wyoming state legislature allocated monies to fund Instructional Facilitators (IFs) in schools around the state. This interview study, developed through situational analysis, explores the roles and responsibilities of IFs in Wyoming secondary schools, and the contextual factors of those schools that impact the work of IFs, particularly those whose work is focused on literacy coaching. Findings from the study include descriptions of common work roles, individual coaching with teachers, providing staff development to groups of teachers, and collection, analysis, management, and interpretation of data. Contextual issues of teacher enrollment and embeddedness in school professional development structure are also presented as of great importance to IFs, and recommendations for IFs’ work in schools, as well as for future research are presented.