Grasslands are complex and heterogeneous ecosystems, and their health can be defined by the cumulative ability of their components to evolve, adapt, and maintain their integrity in the presence of stress/disturbance and provide ecosystem services. Herein, a design approach is used to generate alternative and multifunctional pastoral livestock production systems that enhance grassland health. As a way of understanding the complexity of grasslands and initiating the design process using systems thinking, rich pictures emerge as a useful method. As rich pictures are subjective views, geographic information systems (GIS) could be applied to improve the veracity of their outcomes, as both techniques are forms of an analytical process. This paper reports the application of GIS to a case study of a high-country farm to generate and combine different thematic maps to create a modern rich picture. The rich picture is a combination of remote sensing data (altitude, slope, aspects, and the Normalized Difference Vegetation Index (NDVI)), and on-the-ground data (plant species distribution and diversity and soil chemical, biological, and physical parameters). Layers were combined using a multi-criteria evaluation (MCE) based on the analytical hierarchy process (AHP) to create a final rich picture. The results highlight dissimilarities in perceptions of what underpins ‘grassland health’ between researchers in different fields and with different perspectives. The use of GIS produced a modern rich picture that enhanced the understanding of grassland health and allowed for the identification of gaps, values, and possibilities for future research work.