Background: Critical reflection is an essential curricular component for learning from experience that determines placement quality in postsecondary experiential learning placements. However, there are poor empirical connections between the use of critically reflective processes and learning outcomes. Purpose: This research explored reflective processes professionals use in their practice and how these processes compare with the reflective activities postsecondary instructors in professional faculties use during experiential learning. Methodology/Approach: This collective case study used focus group interviews, field notes, and professional grey literature to examine the research questions. Findings/Conclusions: Professional training programs must align their reflective practices with more integrated and holistic models of reflective practice to better mirror the professional skills demanded in professional practice contexts. Professionals in context-laden professional environments should integrate reflective activities into their practice based on emergent, iterative, and cocreative models that are more like their lived realities at work. Reflective practices which better fit and mirror these lived realities may lead to better connections between reflective activities and work outcomes. Implications: Professional environments are complex, dynamic, and affected by contextual factors. New integrated and holistic models of reflective experience should replace the separated, stepwise, or automatic models that have guided reflective practices in the past.