The purpose of this study was to develop a measure to investigate studio teacher's observational skill as a function of the observer's ability to identify effective pedagogical practices. A secondary purpose was to see if observational skill varied as a function of scores on a measure of empathy. Participants (N = 60) were saxophonists who observed and wrote about the strengths and weaknesses of two 1-minute videos of private saxophone lessons and two private violin videos. To develop expertise criteria, four expert teachers observed the videos for their respective instruments and their responses were converted into lists of strengths and weaknesses. These lists were then compared to participants' responses and used as criteria for determining the degree to which participants' analyses matched the experts' responses. Participants also completed a demographic survey and the Toronto Empathy Questionnaire. Results indicated that the degree to which participants' analyses matched the experts did not vary as a function of teaching experience. The degree to which participants' analyses matched the experts also did not vary as a function of empathy scores, though descriptive trends indicated that higher empathy scores were accompanied by a greater degree of match. There was a significant difference in degree of match between the participants and experts for the saxophone and violin videos. Implications for tool refinement and future research are discussed.