While management research has recognized the importance of a paradox mindset for leaders to manage tensions effectively, little focus has been given to its potential for learning, especially through training interventions. This study explores whether and how managers can improve a paradox mindset through training interventions. The training involved 26 managers across diverse industries, blending lectures, business case examples, and ethnographic exercises over five three-hour sessions. Participants’ paradox mindset generally increased after the training intervention, and inductive analysis and subsequent qualitative comparative analysis (QCA) revealed that improving a paradox mindset is achieved through the simultaneous pursuit of seemingly contradictory processes of simplification with complexification, suggesting that learning about paradoxes is paradoxical. Based on these findings, we develop a model of the learning processes and mechanisms that underlie the simultaneous pursuit in which improving a paradox mindset is realized through multiple pathways with diverse and intertwined learning mechanisms, including cognitive, experiential, and transformative learning. Our findings contribute to both management learning and education and paradox literature by offering a theoretical understanding of improving a paradox mindset and its practical applications for the design of effective training interventions.