The Possibility of ‘Both/And’: Talking Paradox with Dr. Wendy K. Smith

Organizational leaders are often under constant pressure to deliver simple solutions in the face of deeply complex challenges, with confidence and speed. You may experience this as a kind of “either/or” decision-making, a tension between doing things this way or that way. A leader pressured to decide quickly may miss insights that emerge from sitting with the tension within the paradox they face. Amidst these dynamics, can leaders hold the possibility of “both/and”?

Our guest, Wendy Smith, suggests that moving beyond reductionist thinking requires embracing the interdependent tensions of paradox. She encourages us to shift our focus from making forced choices to discovering how opposing forces can reinforce one another. Cultivating “both/and” thinking is no longer a purely theoretical exercise; it is an essential, everyday capability needed to navigate the ambiguity of our changing world, disrupt transactional habits, and build courageous, thriving communities.

Dr. Wendy K. Smith is an expert in organizational behavior whose research focuses on paradox theory and how leaders navigate competing demands to drive creative solutions. She is the co-author of Both/And Thinking: Embracing Creative Tensions to Solve Your Toughest Problems. Recognized as a Thinkers50 top global management thinker and one of the most cited researchers in her field, Dr. Smith is the Dana J. Johnson Professor of Management & Faculty Director of the Women’s Leadership Initiative at the University of Delaware. She will serve as a Fellow at Harvard Business School for the 2026-27 academic year.

This episode

• Challenges the pervasive demand for immediate clarity and rapid decision-making, demonstrating how rushing to resolve ambiguity can diminish both decision quality and human dignity.

• Unpacks the conceptual difference between a dilemma (a choice to be made) and a paradox (interdependent, synergistic tensions, such as stability vs. change or the abstract vs. the practical).

• Plays with the idea of “cauliflower living”—a deep integration where a strong global economy feeds the distinct, hyper-local traditions of communities, an example of “Both/And” thinking that revitalized Fogo Island, Newfoundland.

• Examines how unheld uncertainty breeds a social contagion of fear, proposing building a capacity for collective courage to hold interdependent tensions rather than retreating into polarized camps.

Notes

• 0:00 – The Curriculum of Experience: Navigating complexity and transition

• 5:13 – A Career Dilemma: Finding the integration between medicine and leadership

• 12:04 Engaging in A Paradigm Shift: Moving away from linear reduction and towards holistic and interdependent thinking

• 25:19 – Cauliflower Living: Fogo Island and honoring tradition through modernity

• 44:05 – Interlude: Reflection on learning through paradox

• 46:58 – The Folly of Airport Transactions: Applying paradox in everyday moments

• 1:01:50 – Emotional Contagion: Addressing the fear of ambiguity in within groups

• 1:09:08 – Final Thoughts: “Both/And” as the next core leadership practice

Citations, Papers & Recommended Reading

• Berg, David & Smith, Kenwyn. Paradoxes of Group Life.

• Kerr, Steven. On the Folly of Rewarding A, While Hoping for B.

• Nisbett, Richard & Peng, Kaiping. The Geography of Thought.

Production Credits

Learning Through Experience is hosted by Dr. Heidi Brooks and produced by Emberleaf Studio. Theme music composed and performed by Bradley Kemp.