This article reports on a two-year study of one principal's professional learning practices in "Transform," a professional learning program in Edmonton Catholic Schools, Alberta, Canada. Transform was designed to be a bottom-up, morally-oriented professional learning approach in which principals and teachers worked as partners on critical, participatory action research projects. This article examines the research question "How are principals shifting from technically- to morally-oriented professional learning practices in their schools?" and explores one theme--co-creating social spaces for risk-taking--to illustrate how principals shifted from being managers of teachers' learning to being partners with teachers in researching and refining classroom practices.