By examining the role of supervision in the induction process of second career teachers, this study provides a new lens both for examining the career transition of second career teachers and for viewing the role of instructional supervision. Using case study methodology, the transitions of three cohorts (N=38) of participants in a teacher education program specifically designed for second career teachers and two cohorts (N=12) in a program designed to serve both second career and traditional entry teachers were studied. The data from the cohorts, separately and as a whole, indicate that a model of supervision combining institutional opportunities for dialogue between the second career teacher and his or her supervisor with weekly forums for peer exchange facilitated by a supervisor, was most effective in addressing the concerns of second career teachers. This approach helped them to bridge theory and practice by identifying, adapting, and utilizing their own strengths, and supporting their sense of agency. Findings of the study support a social constructivist approach to teacher education by documenting the relationship between the knowledge and experience individuals bring to the field and the ways in which a dialogical approach to supervision can facilitate the extension and application of this knowledge base to the realities of school. (Contains 35 references.) (Author/LL)