The Yellowstone to Yukon Conservation Initiative (Y2Y) was created in 1993 to advance conservation in a 1.2 million km2 portion of the North American Rocky Mountains. We assembled 21 people with influence over Y2Y in a workshop to elucidate perspectives on challenges and solutions for this organization at a key point in its evolution, and used Q method to define four perspectives on challenges and three on solutions. Participants were differentiated by four models for effecting change—vision-based advocacy, practice-based learning, political engagement, and scientific management—with emphasis on the first three. Those with authority in Y2Y aligned with vision-based advocacy and expressed ambivalence about practice-based adaptive learning and rigorous appraisals of existing strategies. Workshop results were consistent with an apparent trend toward organizational maturation focused on stabilizing revenues, developing formal organizational arrangements, and focusing strategies. Consolidation of power in Y2Y around a long-standing formula does not bode well for the effectiveness of Y2Y. We recommend that leaders in Y2Y and similar organizations focused on large-scale conservation to create and maintain an open system—philosophically and operationally—that capitalizes on the diverse perspectives and skills of individuals who are attracted to such efforts. We also recommend that the Y2Y initiative be followed closely to harvest additional lessons for potential application to large-scale conservation efforts elsewhere.