The demands of the Fourth Industrial Revolution require a workforce prepared to collaborate on the creation of new products, processes, and services in a rapidly changing economy. Driven by this context, higher education is challenged to prepare graduates with the requisite transferable skills they will need to succeed in their careers. The purpose of this action research study was to better understand how co-curricular leadership educators can prepare undergraduate students with the transferable skill of group creativity. An innovation, the Creative Leadership Design Studio (CLDS), was designed using the theoretical and conceptual frameworks of play and improv comedy to introduce students to group creativity. A design studio application allowed students to collaborate to creatively address a problem in their organizations. Through a qualitative multiple case study design, the CLDS was delivered to two groups of undergraduate students. Four sources of data were used to answer the research questions including video observations, written student reflections, researcher journal, and semi-structured interviews. Major findings suggest that the innovation helped students identify and practice the skill of group creativity. Furthermore, play and improv comedy were viewed positively as a way for students to strengthen group bonds and improve creative thinking. In reflection, students indicated that the innovation held relevance to their future careers in preparing them with multiple transferable skills including collaboration, creativity, communication, confidence, and adaptability. These findings indicate that co-curricular leadership workshops using play and improv comedy can positively influence student’s transferable skills growth.