This article describes the Context Based Learning (CBL) redesign of Nursing courses addressing life transitions, including by implementing group discussion, written concept analysis, group presentations, reflections on thinking and simulation performance, group skills analysis and a final paper. The purpose of the study was to determine how these strategies build metacognition and thinking in the students. Both students and faculty participants agreed the structure of the courses stimulated thinking and metacognition, especially through group discussion of the presentations based on the concept analysis. Students said listening and a safe learning environment helped them think and reflect. However, the larger the group and the more faculty controlled the group, the less thinking developed. This study provides insights into the importance of a safe learning environment, listening, group size and faculty control in the development of thinking and self-reflection in small group CBL format that may be applicable to many disciplines.