This paper is an exploration of the pedagogic challenges experienced in teaching emerging Jewish educational leaders about how to lead with a diversity mindset and create inclusive spaces for teaching and learning. Employing elements of self-study and phenomenology, we identify felt difficulties, examining how those were evident in our planning and teaching of the course and in student work. From those challenges we name lessons to be learned and questions for further study about the professional development of Jewish educational leaders who are responsible for creating cultures of belonging in their institutions.