Landscape assessment is used as a professional means for arguing for the values of a landscape. While landscape is increasingly recognised as an entity reliant on the perceptions of those who experience it, assessments tend to remain in the domain of professionals, as objective outsiders. This view sees landscape as a neutral entity, an objective unit of analysis. In this chapter the idea of landscape assessment as a means for engaging with and accepting conflict about landscape as a means for developing a vibrant discourse is put forward, moving beyond landscape assessment as a final product, to recognise it as a discursive learning process. The chapter explores theoretically how assessment can be used to lift plurality of values attached to landscape and help enhance the democratic focus of landscape planning.