Digital technology has improved our lives in different ways and do-mains, also in the education field. Innovative teaching methods should integrate the use of digital technologies to enhance student engagement, support any education environment and encourage both teachers and learners that are now relying on them for a different purpose from con-ducting research to collaborating with peers. The actions have to foster innovative didactics that give value to the learner’s passions and skills, increase flexibility and transdisciplinarity, and boost project-building didactics. These changing are also occurring in the design process education. This paper aims to present a creative learning experience, based on the “flipped classroom” methodology enriched by the integration of other learning engagement strategies, developed by IDEActivity Center to explore the Design Thinking (DT) process and tools. The teaching project promotes forms of innovative learning of the Design Thinking (DT) process integrating different engagement strategies for adult learners including, Think-Pair-Share, Role-play, Flipped–Active Learning, Problem-based learning. The workshop designed for flipped DT learning is an experiential format applicable in any context, whether educational or corporate, in a public or private institution. The learning experience was experimented in a didactic module of Product Design on a Master’s course at the Politecnico di Milano.