As the COVID-19 pandemic caused severe disruption to education enterprises throughout the world, the main response by educational institutions was to move to online learning environments. The purpose of this study was to understand better how instructors could improve online learning for a professional-level week-long short course in a highly technical area (data analytics), which had, pre-COVID, been a hands-on computer, laboratory-based learning experience. The authors used self-study of professional practice to elicit and understand the major issues and concerns of the transition to an online learning environment. Under the guidance of a colleague in teacher education, three course instructors recorded and analyzed their experiences and, through discussion and data analysis, gained a deeper understanding of three challenging dimensions: course adaption to the online environment, personnel considerations, and technological considerations. Through the reflection that self-study provided, several of these challenges were addressed in subsequent courses. Self-study provided the instructors with an opportunity to reflect on the transition of the course to an online environment. This, in turn, provided an opportunity for course improvement and, arguably more importantly, an opportunity for the instructors to better understand each other's concerns and desires as it pertained to the course.