The sustainability of agriculture depends as much on the natural resources required for production as it does on the stakeholders that manage those resources. It is thus essential to understand the variables that influence the decision-making process of agricultural stakeholders to design educational programs, interventions, and policies geared towards their specific needs, a required step to enhance agricultural sustainability. We examined the perceptions, experiences, and priorities that influence management decisions of five major groups of agricultural stakeholders (conventional small grain producers, organic small grain producers, organic vegetable producers, extension agents and agro-industry crop consultants, and researchers) across the Montana, United States. Results revealed that while stakeholder groups have distinct perceptions, experiences, and priorities, there were similarities across groups. Specifically, organic vegetable and organic small grain producers showed similar responses that were, in turn, divergent of conventional producers, researchers, and crop consultants. Conventional small grain producers and researchers showed overlapping response patterns while crop consultants formed an isolated group. Our results reinforce the need for agricultural education and programs that address unique and shared experiences, priorities, and concerns of multiple stakeholder groups. This study endorses the call for a paradigm shift from the traditional top-down agricultural extension model to one that accounts for participants’ socio-ecological contexts to facilitate the adoption of sustainable agricultural systems that support environmental and human wellbeing.