Counseling students facing their clinical fieldwork training often experience significant fear and anxiety. As early as 1984, Brala (1984) discussed the potential impacts of student fears of negative evaluation of their therapeutic fieldwork. These feelings of fear or anxiety on the counseling student’s part have also been shown to be linked to the client’s anxiety and overall therapeutic outcomes. The potential for criticism or negative evaluation is consistent with older, more traditional supervisory models that essentially highlighted ways in which the student was making errors and placed focus on those shortcomings. Fortunately, more strengths-based models have emerged that encourage supervisors to have confidence in their students and avoid a hierarchical relationship between supervisor and student (Edwards, 2013; Edwards & Chen, 1999). This chapter highlights these postmodern approaches to engaging in clinical education and supervision.