School leaders are not adequately trained to supervise music teachers (Powers, 2012). Whereas the areas of expertise of teachers vary, school leaders generally have expertise in one area. This is problematic because school leaders lack the pedagogical and content knowledge that is essential to effective instruction in music (NAfME, 2011; Millican, 2013). This comparative case study was designed to understand music teacher’s perceptions of common strategies used to support their professional growth in comparison to the perceptions of their leaders. Case replication was used to select two music teachers and two school leaders across two contexts. These contexts included a high performing academic school in an affluent neighborhood and low performing academic school in a poor neighborhood. In addition, the music programs from the schools in each of these contexts is high performing. This research revealed several strategies for cultivating teacher growth. These included: (1) professional development opportunities with content specific experts (2) adequate resources and (3) trust in the execution of the evaluation process and evaluator. It was also concluded that teacher age/experience plays a role in how they respond to feedback from leaders. When well received, feedback cultivates teacher growth.