A responsive landscape planning approach is characterized by feedback loops between sensing the environment and the designing and planning process. Advancements in this approach come along with technological developments and the generation of vast amount of data providing many new opportunities but also important challenges. While landscape planning and design requires a thorough understanding of the complex interactions between natural and socio-cultural factors, it is unclear how these new workflows and these data can successfully be implemented to shape landscapes that provide societally valued and needed qualities. We suggest six conditions for a successful implementation of such an approach and illustrate them with various examples. We discuss to what extent this new approach can create a knowledge-driven rather than a data-driven design and planning process and conclude with discussing the potential of the approach to foster social learning enabling shaping and transforming our landscapes.