When teachers consider integrating new or existing forms of technology into their designs for teaching and learning, they need to rethink the existing course design. Emerging mobile and wearable technology enables real-time monitoring and support for collaborative processes. Digital didactical designing (DDD) is the act of modelling and forming the teaching practice for different designs for learning. A main prerequisite for DDD is how institutions look at the teacher's role. Teachers are experts and, when they develop new designs for learning, they are also learners. In a study programme in higher education at Ume University, instructors and teachers reorganized an existing course. The course redesign was conceptually inspired by the design-based research approach. The study aimed to explore new forms of innovative pedagogy, particularly how smart glasses may support student learning when they walk through a flexible learning process. This study provides insights into new forms of innovative pedagogy and how to reorganize teacher teams across existing study programmes.