Existing preparation programmes for school principals have been widely criticized for failing to prepare their students adequately for their future roles. This study investigated a workshop at a principal preparation programme which focused on collaborative learning from personal real-life cases, exploring its potential contribution to the professional development of aspiring principals. Using qualitative methodology, we investigated 99 journal entries written by 12 aspiring principals who had participated in such a workshop. Data analysis revealed three benefits of this way of learning: (1) developing a multidimensional view; (2) acquiring applicable knowledge; and (3); nurturing the ability to doubt. Analysis suggests that collaborative learning from personal cases may be an appropriate pedagogical approach for principal preparation programmes; however, there are some concerns worthy of attention.