This paper investigates how planning practitioners can increase the effectiveness of lesson-drawing from exemplary case studies in sustainable urban transport development. There are a number of cities worldwide that have successfully managed a transition in their transport systems towards providing attractive and efficient structures for public transport, walking, and cycling in liveable communities. Several studies have analysed these successful examples of sustainable transport development, and a related body of literature investigates their transferability to other cities. Based on a review of the existing literature on lesson-drawing and policy transfer, this paper finds that current practice mainly focuses on the content of what has been implemented in exemplary case studies. We suggest that there are additional lessons that practitioners can learn from investigating how a successful program has been implemented, and how practitioners have contributed to this success by advocating their subjects in the political arena. These strategic lessons are especially valuable with regards to interventions that promote sustainability, as these are often discussed in a climate of polarised or adversarial ideas and interests in civil society. The paper concludes with suggesting three areas for strategic lesson-drawing: suitable policy windows, the role of key individuals, and the quality of stakeholder debate