The societal and political pressure of the energy transition, combined with the promising possibilities of a connected, decentralized world within the framework of the Internet of Things (IoT), is accelerating the transformation of cities towards Smart Cities. While there are some flagship cities like Barcelona, Lyon, and Vienna that are harnessing this potential, most cities have a significant catch-up to do. The gap between leading Smart Cities and lagging cities is growing larger. Although the need for action is often recognized, the paths forward are often unclear for decision-makers. What are the core elements of a Smart City? What steps need to be taken from analysis to identifying the sweet spot to developing an action plan? Where is the potential greatest? Where should one start? How are other cities approaching this, and what have they learned so far? What can be derived from Greenfield approaches in Chinese cities?.