Engaging industry operators has proven crucial for implementing emerging Industry 4.0 and 5.0 technologies. As such, platforms that consider operators’ contextual perspectives and their views on the impact of these technologies have both facilitated technology acceptance and, in turn, improved operators’ jobs. However, by focusing solely on employed users, scholars have systematically overlooked the perspectives of potential users, such as job seekers. This paper presents an exploratory study on job seekers’ perspectives. Based on four interactive workshops, job seekers were provided with a platform to discuss (1) their perspectives on two emerging technologies, (2) the anticipated impact on their future jobs, and (3) their vision of digitisation and job transitions. We summarise the set-up and findings of the interactive workshop sessions on digital work instructions and cobots, share key lessons learned, and propose both practical and theoretical directions for future research.