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About Jim Ryan
Jim Ryan served as a dean at Harvard and then as president of the University of Virginia. During his 12 years of leadership, he learned that the right questions matter more than the right answers. His work centers on how leaders use questions to sharpen judgment, build trust and turn conflict into clarity. As dean of the Harvard Graduate School of Education, Ryan delivered a 2016 commencement speech on five essential questions that went viral, viewed millions of times and translated into multiple languages. The speech became Wait, What? And Life's Other Essential Questions (2017), a New York Times bestseller that distills how leaders listen, learn and lead under pressure.
Ryan's forthcoming How About Never? And Other Essential Questions For Leadership and Life (2027) extends that framework into seven questions that define exceptional leadership, from basic questions of identity and purpose to the operational challenges of decision-making and knowing when to change course. The framework is anchored in the conviction that true leadership means putting the interests of the organization above your own. As the ninth president of the University of Virginia (2018–2025), Ryan chaired the Atlantic Coast Conference Board of Directors and the Council of Presidents. He has argued before the U.S. Supreme Court and authored widely cited scholarship on education law and educational opportunity, including Five Miles Away, A World Apart (Oxford University Press, 2010).
Jim's Keynote Topics
The best leaders don't have all the answers; they know which questions to ask. Drawing from the forthcoming How About Never? And Other Essential Questions For Leadership and Life (2027) and 12 years leading Harvard's Graduate School of Education and the University of Virginia, Ryan presents the seven questions that separate good leaders from truly great ones: Who are you? What's the point? How's it going? What would you do? How about never? What can I say? Why not? The framework moves from foundational questions of identity and purpose to the operational challenges of decision-making, communication and knowing when to change course. Each question cuts to the heart of what defines exceptional leadership, grounded in the conviction that true leadership means putting the interests of the organization above your own. Audiences leave with a framework they can apply immediately to sharpen judgment, deepen integrity and anchor every decision in mission and values.
Organizations move faster when leaders and teams ask the right questions. Based on his New York Times bestseller Wait, What? And Life's Other Essential Questions (2017) and his viral 2016 Harvard commencement speech, Ryan presents five questions that build trust, surface assumptions and move teams from reaction to clarity: Wait, what? I wonder... Couldn't we at least...? How can I help? What truly matters? Each question is a tool for honest assessment, courageous conversation and finding common ground under pressure. Ryan grounds the framework in stories from his years leading major institutions and the research on how questions shape judgment, culture and the willingness to take smart risks. Audiences leave with five questions they can use in meetings, one-on-ones and moments of crisis to cut through noise, challenge their own thinking and lead with integrity.
Articles by Jim Ryan
In Praise of Easy Conversations
June 2026The Chronicle of Higher EducationDEI: The Case for Common Ground
May 2023Inside Higher EdCan We Talk?
March 2022UVA TodayOp-Ed: American Democracy Is in Danger. Here's How Universities Can Help Protect It.
June 2021The New York TimesTeacher and Tech: Making the Most of Learning Technologies
June 2016Education WeekJim Ryan's blog, Making the Case: Key Questions in Education Debates
March 2016HuffPostLearning to Live Together
September 2014HuffPostUnderstanding Brown v. Board of Education
May 2014The Chronicle of Higher EducationWhy 'Fisher' Means More Work for Colleges
July 2013SSRNEducational Policy and the Law (5th ed.)
January 2011Jim in the Media

Former UVA President Jim Ryan shares humor and gratitude with the class of 2026

Jim Ryan's podcast, Inside UVA
Jim Ryan on His Journey to Be the 9th President of UVA
5 Essential Questions in Life: A Conversation with James Ryan

What I'm Reading: Wait, What? James E. Ryan
Asking the Right Questions: An Interview with James E. Ryan

These 5 Questions Might Boost Your Curiosity—and Make You Happier

How A Harvard Dean's Commencement Speech On Life's Big Questions Went Viral

5 Essential Questions of Life with Dean James Ryan

Want to be happy? Be curious

Wait, What?' (And Other Big Questions)
Harvard dean on book inspired by his popular graduation speech
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