The emerging field of educational visioning is full of challenges and phenomena worthy of careful analysis and documentation. A relatively neglected phenomenon is the learning curve of the leaders (often lay leaders) involved in the visioning process. This article documents a range of experiences of the author serving as a vision coach to five different institutions. The importance of treating the educational leaders involved in the process as learners is a consistent theme across five institutions. The tendency in the field is to think of them as transformative agents for congregational change. The author argues that this admirable goal can only occur with considerable attention to the pedagogy of teaching vision. This is a particular challenge given the highly abstract and conceptual framework of the volume "Visions of Jewish Education" (Marom, Fox, & Scheffler, 2003), which often serves as the "text" for the visioning process. (Contains 1 figure.)