Collaborative inquiry and conversational learning are approaches to management education and learning in which participants construct knowledge together through dialogue. Both approaches advocate letting go of control to allow insight to emerge through free-flowing conversation, but little has been written about how to accomplish this. Furthermore, these approaches contradict expectations about learning among both teachers and students and raise fears of discussion degenerating into pointlessness. This article presents the idea of “meandering”—wandering casually without urgent destination—as a way of framing a conversation process that can help management educators loosen control without being out of control. It is based on a case of group learning generated by the six authors at the 2019 Research in Management Learning and Education Unconference. Our conversational learning process, which we described as meandering, was not only pleasant and rewarding but also led to a concrete action plan and research agenda. In this article, we demonstrate and discuss the highly relational, embodied, and contextual nature of meandering and propose a research agenda for generating more knowledge about this method and how to put it into practice in management learning and education.