This article discusses a design research project in which design practitioners and researchers collaborated to develop training guidelines and a toolset for astakeholder workshop to be implemented by partner organisations of the Arts on the Margins: Arts as Social Sculpture (AMASS; 2020–2023) project. It focuses on the learning experiences of the design team, which was comprised of four people who created the online environment for the stakeholder workshop.The team members, who are also the authors of this article, were all designers and researchers with varied backgrounds and experiences. The workshopactivities were adapted from a face-to-face format to an online environment due to the COVID-19 pandemic. The objectives of the article are to explore the team dynamics, approaches to design development within digital environments. The use of collaborative autoethnography (CAE) and reflection enabled the design team to assess their design processes and learn from critical discussion. The results will present guidelines for teams developing and conducting online workshops in digital environments.