The purpose of this research was to investigate a formal principal mentoring program and report on perceived learning benefits and the well-being of the participants. The study highlights aspects of the mentoring relationship evidenced in the explicit and intentional development of school leaders. The empirical investigation used qualitative-naturalistic inquiry methods. Data were collected primarily through in-depth, focused participant interviews. The findings of this study revealed both the "what" and "how" of perceived benefits within formal mentoring relationships under the direction of a state-wide programmatic initiative. Of particular interest was the role of social learning through reflective activity and the results of occupational well-being. A truthful representation of aspects of mentoring relationships between novice and mentor principals within formal programming provided insights into how novice learning supports their well-being. Implications for the development and retention of principals are considered.