The broader framing of the decision-making processes of stakeholders within the sustainability debate is explored in the context of a paradigm shift that acknowledges the world as a complex, dynamic system. There is merit in adopting a paradigm informed by, and therefore suitable for dealing with, living systems, particularly as the paradigm is founded on holistic and flexible strategies. To move the discussion forward, a key concern examined here is what this different paradigm means for engaging and motivating stakeholders. Through questioning established notions of ‘stakeholder’ as defined in the business literature, and the traditional models of sustainable development, an alternative model of sustainability is presented that is grounded in a different worldview. The implications are considered of how the paradigm’s adoption and the associated model of sustainability would change current practices for motivating social transformation in the built environment through stakeholder engagement. Three major shifts in thinking implicit in such a new model of sustainability are identified and examined: creating effective change in the complex social–ecological system presented by the built environment; how this worldview would redefine current notions of stakeholder engagement; and what the implications would be for mechanisms such as assessment and rating tools meant to change stakeholder behaviour.