As uncertainty rises, people often look to leaders for greater certainty. Yet the more complex the environment becomes, the less credible it is for any one person to claim they have the answers. The leadership challenge is no longer simply making better decisions. It is creating the conditions for better questions, broader participation, and stronger collective judgment.
In this episode of Partnering Leadership, Mahan Tavakoli speaks with Larry Robertson, leadership advisor, Fulbright Scholar, and author of Great Question: The Art of the Ask and Getting More of What You Really Want. Drawing on his research into entrepreneurship, creativity, and leadership under uncertainty, Larry explains why questioning is not merely a communication technique. It is a core organizational capability that helps leaders test assumptions, recognize emerging threats, and see opportunities before they become obvious.
The conversation examines the difference between asking more questions and building a genuinely questioning culture. Larry challenges leaders to consider whether the questions inside their organizations are authentic or simply statements disguised as questions. He also explores who is permitted to ask, which questions receive serious attention, and whether senior leaders are willing to be changed by what they hear.
Mahan and Larry also address the growing role of artificial intelligence. AI can identify patterns and generate predictions from what has already happened, but that raises a consequential leadership question: What happens when the assumptions embedded in historical data no longer hold? Their discussion reveals why human curiosity, contextual judgment, and intellectual humility may become more important as AI becomes more capable.
Throughout the conversation, Larry offers memorable ways to strengthen leadership judgment, from learning to “quiet your cleverness” and “listen atmospherically” to distinguishing functional questions from the great questions that shape strategy and direction. This episode provides a practical and timely examination of how CEOs and senior executives can lead without pretending to possess certainty they do not have.
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