The future of work and learning will take place in two-dimensional, online settings, even if these virtual formats are used to augment in-person experiences. In this chapter, the author reflects on his improv theater and teaching experiences to offer practical advice on enhancing collaboration in small, synchronous online meetings, both in the classroom and workplace. Core principles include engaging selflessly, honoring the power of empty space, and bringing emotional and physical energy to each online session. The author shares lively examples from his own theatrical experience and supports the use of basic improv principles through social science, neuroscience, and workplace engagement research.