This study aims to examine the use of reflective pedagogies in sustainability leadership education by investigating two specific pedagogical tools—the Portfolio and Pod—employed by the Master’s in Strategic Leadership towards Sustainability (MSLS) program at Blekinge Institute of Technology in Karlskrona, Sweden. The study analyzed data gathered from student surveys, teacher interviews, and staff reflections to determine the benefits and challenges faced by students and staff in implementing and engaging with these pedagogical tools. Benefits include the provision of distinct structures to guide student reflection towards individual skill development and the use of collective reflection to encourage generative dialogue between students and staff. This holds benefits for collaboration, self-awareness, understanding of multiple perspectives, and creating self-directed graduates. Staff and students also, however, suggest a number of challenges. These include the ‘constrictive’ nature of guided reflection and the emotional and mental load faced by staff in hosting and holding students through often challenging personal reflective processes. For the potential of reflective pedagogies to be truly realized for Education for Sustainable Development in higher education institutions need to develop an understanding of the impacts that reflective pedagogies have on students and teachers and create institutional structures to support them.