In this study, we investigate the benefits and barriers to postgraduate students' employability skill attainment through an in-person, boardroom role play activity titled "Theatre of the Board." We use a case study approach that incorporates mixed methods to analyse 157 pre- and post-survey student responses and twelve reflective logbooks. Over a two year period we measured students' employability skill growth through a "Theatre of the Board" role play. Students play-acted boardroom positions, requiring highly spontaneous and creative solutions to collective problem solving. The results show that students improved their cultural awareness, reflective learning and problem-solving. On the other hand, students' self-confidence with time management, interpersonal and oral communication skills decreased over time. Based on the findings, we present key recommendations to advance role play curriculum design while considering employability skill attainment as a key component to experiential learning outcomes.