This paper offers a model of supervisory collaboration that brings teacher and administrator programs together through a lens of formative evaluation. The roles of teacher and principal must be collaborative to sustain student success, yet the preparation models for those respective positions are often isolated from each other, as varying university departments and focus areas exist in silos. Preparation programs must maximize the clinical experiences of teacher education and administrator preparation programs, with a focus on practical teaching strategies and authentic feedback to pre-service educators and their instructors for reflection and change. This paper overviews a collaborative supervision model and incorporates case study vignettes focused on reflective supervisory practices in a STEM instructional environment.