A bossless organisation, in which employees self-select to projects with minimal or no interference from management, is an emerging phenomenon that has attracted the attention of scholars and practitioners. The understanding of the benefits and costs of this new organisational form is, however, limited. In this paper, we develop an agent-based model to investigate the benefits of the bossless form and compare its efficacy in terms of project selection and asset allocation with that of a traditional hierarchy. Our results suggest that the relative balance between the organisation’s resources and number of opportunities it faces plays a critical role in determining the advantages of the bossless form of organising, which performs better when resources are highly constrained relative to opportunities. We analyse the mechanisms and boundary conditions and discuss potential applications of our findings to the study of organisation design.