This chapter is about an attempt to change, through planning practice at municipal level, the dominant planning culture. In Portugal, spatial planning has been clearly dominated by the blueprint approach. There are two main structuring circumstances that contributed significantly for the current state of the art in Portuguese planning system. The first is associated with the nature of the planning problem and the ideas about planning that became dominant and widespread when, in the 1940s, the planning system was definitively perceived as a relevant branch of public policy. The second is related with the political regime, the New State dictatorship, under which Portugal lived during 48 years. The initial step in the first stage of the planning process is, naturally, to become acquainted with the community and the municipality. The political attitude, at the level of the municipal Executive Council, towards plan-preparation can vary significantly.