Online teaching faces the challenge of using roleplaying as a tool to promote cognitive rehearsal (CR) and skills acquisition in management. COVID-19 has forced many face-to-face (F2F) higher education courses to go online, adding to the challenge. However, in the face of COVID-19, many educators have quickly adopted Zoom and similar videoconferencing platforms (VP) to carry on synchronous education. Roleplaying over a VP could promote CR and skills acquisition in an online learning setting. Research shows that studies on activities that promote deeper learning principles (DLPs) have historically been less likely to be done in an online setting. We propose to use and evaluate a synchronous, roleplaying module administered over a VP to a class of undergraduates studying the social and political environment of business as an aid to improving understanding the diverse social and political perspectives of various stakeholders in business.