The rapid outbreak of COVID-19 pandemic has accelerated the adoption process of digital online tools for social communication across disciplines regardless of cultural backgrounds. Design to had to quickly migrate a considerable portion of its activities to the Internet, making it the preeminent platform in which a large portion of workshops take place nowadays. This swift change from a ‘face-to-face’ to ‘online’ reality is by no means without problems and hurdles, a significant one among these, is the scarcity of academic documentation that deals with the workshops from a communication point of view (beyond the technical aspects). This study aims to identify communication problems within ‘Online Design Workshops’ allowing the organizers to reroute efforts, from a technical and administrative point of view to the quality of the design output itself. The research method adopted was participatory research praxis based on the comparison of survey outputs taken during ‘face-to-face’ and ‘online’ workshops conducted between years 2012 ~ 2019, and 2020, respectively. Using the SMCR model as a framework of communication analysis it was discovered that the most critical aspects are those related to ‘understanding’ (between participants, of the online tools, and of the contents). Accordingly, a first attempt at optimal heuristic paths to the improvement of design stages within online workshops with focus on communication are proposed. Further design workshops can be approached using the process outlined in this paper, adding to the robustness of the heuristics.