The paper summarizes the experiences of working for a decade to promote the transition of courses toward the CDIO framework. It presents a list of lessons learned when applying the CDIO principles in master-level classes in the field of Mechanical Engineering. The paper aims to formalize operational guidelines, serving as a platform for further discussion and as a set of practical recommendations for teachers and educators initially redesigning their courses toward a more CDIO-oriented structure. The paper initially presents the rationale formoving toward CDIO and describes where and how data were collected. Further, it lists several lessons learned for teachers on (1) how to support students in maximizing their learning opportunities in a CDIO context, (2) how to manage the relationship and engagement with company partners, dealing with expectations, trust, flexibility, and visibility.