This paper explores how the concept of "the facilitator as a fool" can be used as a guiding principle for supervising students at universities adhering to problem-based learning pedagogies. With the example of students enrolled at spatial planning studies, the paper argues that students should learn how to face uncertainty and take matters into their own hands. For this purpose, the paper proposes that supervisors act as "fools" in their conversations with students, mimicking a reflective practice. The paper reflects on how this concept fares when applied to a real-life situation of supervising planning students at both Bachelor's and Master's levels at Aalborg University in Denmark. In the end, the paper concludes that the applied concept can work to a certain degree, but it also requires a supervisor who is familiar with the theoretical and methodological "landscape" that students need to navigate in, and through, to become professional and reflective practitioners.