The scientific literature provides a description of various models depicting autonomous agricultural machines working to complete typical field operations. Many of the models involve some form of automation interface that is used by the machine owner to supervise the operation of the machine from a remote location. The objective of this study was to interview experts in the design of autonomous agricultural machines (university researchers, entrepreneurs, and leaders in the agricultural machinery sector) to ascertain their opinions about future autonomous agricultural machines, particularly related to how such machines will be supervised by the machine’s owner. Of the four remote supervision concepts described by participants (within the field, close to the field, from the farm office, and outside the farm site), the close-to-the-field remote supervision concept was determined to be the most viable concept. Designers were divided on the idea of providing real-time live video on the automation interface, however, most of them believed that having live video would reassure the farmer that everything was going well. Desktop computer, tablet and phone were the main devices recommended as tools for remote supervision (i.e., the hardware on which to display the automation interface), with tablet perhaps being the preferred alternative.