Conservation of ecosystem services in agricultural regions worldwide is foundational to, but often perceived to be in competition with, other societal outcomes, including food and energy production and thriving rural communities. To address this tension, we engaged regional leaders in agriculture, conservation, and policy from the state of Iowa (USA) in a participatory workshop and follow-up interviews. Our goal was to determine constraints to, and leverage points for, broad-scale implementation of practices that use perennial vegetation to bolster ecosystem services in agricultural landscapes. Qualitative analysis of workshop and interview data highlighted the complexity involved in achieving multi-objective societal outcomes across privately owned, working landscapes—especially as the Corn Belt region enters a period of rapid reorganization driven by the demand for bioenergy crops. These leaders indicated that initiatives focusing on perennials have the potential to span differences between conservation and agricultural interests by blurring the distinction between working lands and protected areas. Landscape change that transcends private property boundaries to accomplish this goal is dependent upon: (1) facilitation of vertical and horizontal forms of social capital between social actors from different scales and perspectives, and (2) scale appropriate mechanisms that increase the value of perennial practices for farm owners and operators. Our data highlight the adaptive capacity of regional actors to act as intermediaries to shape macro-scale markets, technologies, and policies in ways that are compatible with the needs, the capabilities, and the conservation of local human and natural resources.