Business education and workplace learning are addressed via five episodes or conversations between two business educators, one of whom is experienced and also an improvisational artist. Vaill (1989) compared managing to a performing art. Vendelø (2009) connected organizational learning to improvisation. In these constructed conversations, the improvisational nature of Decision Sciences is extended with dialogues on learning assessment, memory and pedagogical strategies, semiotics (learning via signs), technology and visual learning, and adult cognitive development. Connections to past and current writings on these topics are made, and practical examples provided for each conversation. It can be seen that improv adds insight into what McCormack et al. called "learning to work" and "learning a new kind of learning." These conversations can be viewed as multiple frames to foster analytical and critical thinking skills by business students.