Graduate educators are tasked with helping students connect theory to operationalized learning and practice. This connection represents the learning that graduate students must bring to the workplace to recognize the relevance of their education. Thus, graduate educators must be diligent in designing viable pedagogies in graduate programs that evoke deepened learning that can be translated into action in the workplace to meet the call by organizations. This chapter reviews critical reflection practices and their use as viable assessment mechanisms for student learning outcomes in graduate programs. The teaching styles required by graduate educators to successfully implement these critical reflection learning designs are also examined. The review and examination are conducted through the lens of transformative learning theory, a learning orientation grounded in constructivism and adult learning that occurs when the learner experiences a shift in beliefs, perspectives, attitudes, habits, and actions.