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Weick recommended organizations to “Complicate Yourself” (Weick, 1979, p. 243) on the path to developing “complicated understanding” (Bartunek, Gordon & Weathersby, 1983), being curious about “contradictions” and “embracing criticism” (e Cunha, Clegg, Rego & Berti, 2021, p. 187). A pathway for fostering complex understandings, paradox theory (Smith & Lewis, 2011) increasingly forms part of both organizational development practice as well as curricula and programs of higher education. This PDW seeks to help change agents, educators and others professional helpers complicate not only their learners, but also themselves exploring new paradox pedagogical strategies (e.g., Lewis & Dehler, 2000). Prioritizing time for interactivity, we zoom in on three contemporary paradox pedagogy challenges related to leadership development, sustainable transformation and emotions in paradox facilitation work. This PDW provides participants with several benefits, including: 1) an overview of paradox pedagogical strategies of paradox and associated opportunities and challenges, 2) round-table discussions (with handouts) of facilitation tools, pedagogical strategies, and exercises for aspects of paradox exploration for developing interventions or course work and 3) a widened repertoire of instructional techniques to effectively facilitate paradox-theory informed productive interactions for developmental purposes in organizations and higher education.