AbstractAnnual meetings have the potential to be used to promote the objectives of a society in a unique setting. A carefully selected venue will not only enhance the experience but also promote the very essence of the society. However, conference organisation can also be a minefield of unexpected problems caused by the involvement of diverse service providers. The cost to members can easily exceed the benefits they experience.Critical systems thinking provides a framework of understanding for promoting holistic thinking and sensitivity to underlying assumptions, guiding the organiser to include multiple perspectives. In this paper, the systems approach, along with elements of critical systems heuristics, Ubuntu, and servant‐leadership, are used to reflect on the organisation of the annual meeting of an international systems organisation. The choice of venue provided both opportunities and challenges.The reflection on the process focuses on the fluidity of boundaries and the interplay between systemic planning and systematic implementation.