Despite the emerging recognition of the pivotal role played by professional agency within work contexts, little is known about how agency is promoted and enacted in organised work-related learning settings. This chapter focuses on the work conference as an orchestrated agency-promoting learning arena. We understand professional agency as a necessary precondition of work-related learning, and we emphasise the potential of work conferences to activate and promote such agency. Our empirical study investigated three work conferences in education and healthcare organisations in Finland. Utilising assessments, the investigation addressed how the participants perceived the conditions for learning and the learning outcomes in these conferences. The work conference was mostly viewed as a worthwhile learning arena. The conference advanced participants’ professional agency and participation across entrenched professional boundaries, and work-related learning occurred at both individual and collective levels. A comparison of the three work conferences indicated that in terms of the generation and actualisation of innovative developmental discussions, the most prominent learning outcomes occurred when the participants were able to enact substantial professional agency, when there was comprehensive participation from the work community, and when boundary crossing occurred. This paper contributes to the understanding of the conditions that impede or support work-related learning.