This chapter is presented especially for the use of practicing planners. Practicing planners, as intended here, are broadly defined and inclusive as a set of local stakeholders. Given the widespread need to develop an active civil society, it is important that representative local actors, and diverse urban and regional stakeholders engage in developing their communities intelligently over sustained long-term futures. Practicing planners in this context include, but are not limited to professional urban and regional planners. Citizens and other professionals, such as business persons, bureaucrats from all levels of government, employees from nongovernmental public organizations and their volunteers, and other individuals all have stakes in, and contributions to make to the development of their city-region in the relatively new context of a globalizing and increasingly knowledge-based world economy and networked society. The chapter, therefore, presents the background to these new development dynamics and it introduces the ALERT model. In the form of a conceptual framework, the model is a planning support system designed for the use of the diverse and wide-ranging stakeholder-planning practitioners who seek to engage planning in the steering of these new technology-enabled and knowledge-based development forces to attained desired outcomes. The ALERT model is not so much directly prescriptive, rather it is directional and relational with the intention that engaged planning practitioners will design and tailor their own planning processes to be responsive to local demand and need. At its best, the model can catalyze and stimulate the stakeholders to invent their own strategies that capitalize on the unique assets and development potential of the locality’s communities.