Conventional academic debate on sustainability and transformation has begun to be disputed by researchers, policymakers and other stakeholders from the private sector. The complexity of linking sustainability with transformation necessitates the development of new ways of understanding and explaining actors, processes, issues, structures, and outcomes related to transformation to sustainability (T2S). A persistent problem in understanding and managing the T2S is the implied notion of a monolithic transformation to achieve sustainability. This notion underestimates the diversity of actors as well as the historical contexts of transformations. At the same time, achieving T2S is highly dependent on technical solutions as well as policies that can stir needed behavioural change, whereas these technical solutions and policies are not always socially acceptable or politically implementable. Therefore, achieving T2S also calls for evaluating normative foundations of policies and actions needed to advance T2S. This article argues that T2S is composed of different phases, each of which having a different set of actors, resources and audience. This article explains how collective decision can be achieved through multiple levels and types of negotiations that occur in an orchestrated manner. To understand this, this article introduces a theoretical model as an analytical framework to structure how T2S unfolds. This model uses insights from negotiation studies to focus on the actors’ perspectives on T2S. It proposes the division of the transformation process into phases – entry point, learning, sequencing, disrupting and fortifying. Using the Germany’s energy transition (Energiewende), each of these phases is analysed to determine the “quality” of cooperation that can help fulfil the tasks required to master the so-called “cognitive games” of T2S (ripeness game, power game, bargaining game, policy game, scaling game). Moreover, insights are presented to explain how the designated milestone can be achieved that indicates the advancing to the next phase and eventually entrench the transformation process. The lessons and findings resulting from the analysis of the phases of T2S suggest that there is also the need to revisit underlying assumptions on negotiations, sustainability and transformation.