Over a decade after the regulation change in Virginia allowing individuals without teaching experience to pursue school counseling careers, no known study had focused exclusively on differences site supervisors observe when training school counselors from different professional backgrounds and the extent to which those counselors employ a tailored supervision approach in the clinical setting. While site supervisor training has been an area of interest in recent articles (e.g., Dollarhide & Miller, 2006), its relationship to supervision philosophies and technique differentiation has not been previously addressed. The researcher investigated those topics using a mixed-method research design shaped by suggestions from recent literature (e.g., Better-Fitzhugh, 2010; DeKruyf, 2007; Luke, Ellis, & Bernard, 2011; Miller & Dollarhide, 2006; Peterson & Deuschle, 2006; Stephens, 2008). This study analyzed site supervisors’ perspectives on supervision, the role training can play in developing site supervisors’ confidence and philosophical orientation, and the beliefs and practices site supervisors employ when supervising former teachers and non-teachers. Observed differences between former teachers and non-teachers in the clinical setting existed, yet 7 out of 12 site supervisors did not differentiate their supervision approach in order to close this gap. Findings from both Phase I (survey) and Phase II (interview) of this study indicated that practice is linked to training. Site supervisors who reported receiving supervision training were more likely to work from a philosophy of site supervision, feel more confident about their ability to supervise, and believe that differences between former teachers and non-teachers were slight and could be overcome with supportive, intentional supervision.