This article discusses issues that emerged from conducting professional development activities for educators during the COVID-19 pandemic. In 2020, as post-academic educational trainers, the authors worked closely with more than 200 professional educators who participated in an international diploma program to develop their professional skills and gain positive and insightful experience. Here, they share three lessons they learned while working with professional educators: (a) teachers face new challenges in the use of educational technology, (b) teachers wonder how to motivate learners with diverse abilities in a virtual setting, and (c) building a supportive community is essential. Suggestions and recommendations are also provided.