Generally, one-to-one music lessons in tertiary settings are delivered by practicing professional musicians. While contemporary musicians draw upon a broad foundation of musical skills, they tend to develop highly specialized skills in a narrow area of performance. This may not be ideal for the one-to-one teaching studio, a situation that calls for a broad repertoire of teaching strategies tailored to individual student needs. This tension is exacerbated, as one-to-one tertiary performer-teachers are often employed on a sessional basis, and as such are offered limited opportunity to receive feedback or professional learning related to their one-to-one teaching practice. This article presents findings from a pilot study employing a peer observation and collaborative reflection approach to professional learning conducted by two contemporary trumpet performer-teachers. Similarities and differences between teaching strategies were identified in order to develop a broader range of teaching strategies that the participants might draw on in the future. In turn, the efficacy of a peer observation and collaborative reflection approach to professional learning for the participants is discussed.