Watershed investments, whose main aim is to secure water for cities, represent a promising opportunity for large-scale sustainability transitions in the near future. If properly designed, they promote activities in the watershed that enhance ecosystem services while protecting nature and biodiversity, as well as achieving other societal goals. In this paper, we build on the concepts of ecosystem services and boundary work, to develop and test an operative approach for designing and assessing the impact of watershed investments. The approach is structured to facilitate negotiations among stakeholders. Its strategic component includes setting the agenda; defining investment scenarios; and assessing the performance of watershed investments as well as planning for a follow-up. Its technical component concerns data processing; tailoring spatially explicit ecosystem service models; hence their application to design a set of “investment portfolios”, generate future land use scenarios, and model impacts on selected ecosystem services. A case study illustrates how the technical component can be developed in a data scarce context in sub-Saharan Africa in a way that is functional to support the steps of the strategic component. The case study addresses soil erosion and water scarcity-related challenges affecting Asmara, a medium-sized city in Eritrea, and considers urban water security and rural poverty alleviation as two illustrative objectives, within a ten-year planning horizon. The case study results consist in spatially explicit data (investment portfolio, land use scenario, impact on ecosystem services), which were aggregated to quantitatively assess the performance of different watershed investments scenarios, in terms of changes in soil erosion control. By addressing stakeholders' concerns of credibility, saliency, and legitimacy, the approach is expected to facilitate negotiation of objectives, definition of scenarios, and assessment of alternative watershed investments, ultimately, to contribute to implementing an adaptive watershed management.