Purpose: The purpose of this study is to review literature relevant to leader transition and the navigation of polarities, paradoxes, and dilemmas that exist in organizations. Furthermore, the researchers aim to critique the literature and provide suggestions for practitioners and researchers interested in leader transition through the lens of polarity, paradox, and dilemma. Design/methodology/approach: The authors conducted an extensive review of the literature for this study. They searched the following databases: ABI/INFORM, Academic Search Premier, Business Source Premier, PsychInfo, and Dissertations Abstracts. To conduct their search, the researchers used the terms; leader, manager, and supervisor in conjunction with the terms transitions, adaptation, socialization, assimilation, polarity, paradox, dilemma, polarity thinking, polarity management, leadership, team, organization, conflict management, creativity, and combinations of the same. Findings: There is very little research conducted on either topic independently and no research conducted on both collectively. The literature on leader transitions also states that transitions are times of uncertainty and stress. The findings suggest that some of this uncertainty and stress could result from the inability to recognize and manage polarity, paradox, and dilemma. Furthermore, the literature does not acknowledge this connection nor does it specify the polarities that exist for leaders in general or leaders in transition. Originality/value: Based on personal experiences working with organizational leaders and training and organization development professionals, the authors believe that there is great potential to help train new leaders on polarity thinking. If training and development professionals see value in polarity thinking for transitioning leaders and can respond with timely training interventions, it could have a positive impact on new leader effectiveness and subsequent organization performance. (Contains 2 tables.)