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Some school districts are exploring mentorship to help teachers enact more effective classroom practices that lead to higher student outcomes. The Good to Great study, by the National Network of State Teachers of the Year outlined the professional growth opportunities that state teachers of the year (STOYs) perceived as contributing to their success in the classroom. Although the STOYs noted that mentorship was a key factor, the original study did not examine how different generations of educators may respond differently to mentorship based on their generational cohort identity. The purpose of this nonexperimental, causal-comparative study using Good to Great data was to examine how STOY Baby Boomers and Gen Xers perceived specific attributes of official and unofficial mentorship. Strauss and Howe's generational cohort theory and Zachary's mentoring theory provided the theoretical foundation. The research questions examined whether there was a significant difference between STOY Baby Boomers' and STOY Generation Xers' perceptions of (a) official mentors' and unofficial mentors' levels of empathy, (b) the alignment of personality to the mentee, and (c) their ability to offer support. In a secondary analysis of the existing data, Hotelling's T2 tests indicated that Baby Boomers and Gen Xers did not show a significant difference in their overall perceptions of official nor unofficial mentoring factors. However, a post hoc analysis indicated that Baby Boomers had a significantly higher (p = .01) perception of official mentors' personality alignment to the mentee. The positive social change implication of this study is the potential to increase student learning by designing more effective mentorship programs to meet the needs of different generations of teachers.