As the “impact agenda” continues to gain prominence internationally, a key challenge is enabling academics and policymakers to interact so that they can learn effectively from and with each other. There is an ethical position that, if we could contribute to policy change impacting on work, society, and environment, then some of our resource and effort should be focused in this way, to bring the benefits of our research to the world of policy and practice and to gain insights about the use and potential direction of our research. We argue that there are significant cultural incompatibilities between academia and policymaking, but we propose an approach that establishes a learning zone in which key cultural rules are suspended (not “solved”) and groups can contribute input and extract learning insights as if they were collaborating with shared understanding, when this may only partially be the case. We explore the theoretical grounds and design principles for this new kind of learning zone, which we term the “paradox box.”