At the heart of the educational vocation is a drive to influence, to meaningfully affect the learning and development of others. For adult educators working in higher education, daily activities--from teaching classes to supervising student research to attending faculty meetings to sitting on advisory boards--are full of opportunities to influence. Most educational literature, however, provides little insight into the way adult educators relate to their drive to influence and how this relationship affects their capacity to generate learning, both in the classroom and in their broader professional setting. By analyzing the experiences of an instructional team in teaching and inter-faculty dialogue in a higher education context in Chile this study characterizes the varying ways adult educators relate to their drive to influence. In this paper, I draw on theories of adult development and adaptive leadership, my own ten years of teaching and professional development experience in diverse adult education field settings, and research materials gathered in six semi-structured interviews with four instructors in the team. Overall, I analyze how adult educators make meaning of their drive to influence when faced with complex challenges requiring adaptive learning. I describe the two dynamic psychological processes they experience while in action: (a) the defensive behaviors they employ and (b) the recuperative tactics that enable them to think and act more strategically. By exploring how these adult educators relate to their drive to influence, this article builds understanding of the efficacy of the different psychological mechanisms that adult educators employ in attempting to facilitate learning and change among their students and colleagues. I argue that in order to increase effectiveness in mobilizing learning, adult educators must work to develop a vigilant relationship to their drive to influence, characterized by self-observation in action and greater tolerance for uncertainty.