In the twenty-first century, learning and teaching at school must prepare young people for engaging in a complex and dynamic world deeply influenced by globalisation and the revolution in digital technology. In addition to the use of digital technologies, is the development of flexible learning spaces. It is claimed that these developments demand, and lead to, enhanced reflective practice by teaching practitioners. This article is based on a project that has used multiple New Zealand case studies to engage teachers and leaders in interviews to explore their experiences at the futures–digital–reflective intersection. Critical theoretic and critical hermeneutic approaches inform the exploration of the relationships between reflective practice and twenty-first century learning by analysis and comparison of educational theoretical discourses with voices from a group of principals and ex-leaders on the one hand, and teachers, on the other hand.