This study contributes to our understanding of contemporary leadership as fraught with paradox and complexity and to the emergent field of paradox pedagogy (Knight & Paroutis, 2017; Lewis & Dehler, 2000) by providing insights into managerial paradox work in practice. Specifically, we explore the nature and dynamics of complexity reduction (taming) and complexity amplification (wilding) of paradox in facilitator-assisted paradox navigation in action learning – a type of intervention highlighted as relevant, yet underexplored and characterized by unrealized potential in practice by extant research in both paradox and action learning (Fairhurst, 2019; Edmonstone, Lawless & Pedler, 2019). This study explores the facilitation challenges of activation of theoretically informed notions of organizational/leadership paradox in the context of middle-managers participating in a six-months action learning research project (Revans, 1998; Pedler, 2021). Conducted from a constructionist point of departure, a Reflexive Thematic Analysis (Braun, Clarke, Hayfield, Davey & Jenkinson, 2023) of 20 hours of tape recordings of action learning interventions result in seven themes, dynamic tensions between tame/taming (complexity reduction) and wild/wilding (complexity amplification) of paradox in action learning. Interestingly, both participants and facilitators engage in taming and wilding of paradox leading to both productive as well as unproductive engagement with paradox. These findings question and supplement existing notions of paradox learning journeys as either virtuous or vicious and provide guidance for managers and facilitators on how to stay with the paradox without reducing it to a problem or become paralyzed by complexity, in effect creating paradox staying power for actors in organizational development.