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. This study employed a survey of multiple-choice and open-ended questions to examine the perceptions, experiences, and priorities that influence management decisions of agricultural stakeholders across Montana, United States. A total of 272 respondents completed a survey, representing five distinct agricultural stakeholder groups: 103 (34.9%) conventional producers, 78 (28.7%) consultants, 37 (13.6%) researchers, 33 (12.1%) organic grain producers, and 21 (7.7%) organic vegetable producers. The results revealed that, while stakeholder groups have distinct perceptions, experiences, and priorities, there were similarities across groups (pseudo-F = 22.92, p = 0.001). Specifically, organic vegetable and organic small-grain producers showed similar responses that were, in turn, divergent from those of conventional producers, researchers, and crop consultants. Conventional small-grain producers and researchers showed overlapping response patterns, while crop consultants formed an isolated group. Six clusters resulting from the classification of the multiple-choice response dataset associated with specific agricultural professions (χ2 = 549.72, p = 0.001). The classification of open-ended questions that assessed agronomic challenges and research needs resulted in six distinctive clusters, with specific associations between clusters and agricultural stakeholder groups (χ2 = 164.41, p = 0.001). These 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.