Online preparation of professionals is increasing in higher education, which in educational leadership preparation programs raises the need for a means to provide authentic simulations of leadership experiences and help aspirants learn from them. This study presents a content analysis of 826 responses from 59 different school leadership students who, following each of the 14 simulations they experienced, wrote one response in an asynchronous format as a form of self-debriefing. The five themes identified map to the four phases of the experiential learning cycle (Kolb, 1984), suggesting that virtual opportunities to practice leadership in simulations may serve as grounding experiences after which developing professionals can reflect upon, integrate with new understandings, and try out alternate approaches. This study demonstrates the purpose of self-debriefing following online simulations of relevant professional experiences and how self-debriefing may propel students through the full experiential learning cycle, offering a valuable avenue for professional development in higher education.