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.
Actionable Takeaways
- You’ll learn why rising uncertainty should produce more and better questions, even as employees, boards, and stakeholders increasingly pressure leaders to provide definitive answers.
- Hear how the expectation that senior leaders should have all the answers can weaken organizational judgment and prevent essential information from reaching decision-makers.
- You’ll discover how to distinguish authentic inquiry from questions that are actually statements, challenges, or tests of allegiance.
- Hear why a questioning leader and a questioning culture are fundamentally different, and what must change before people throughout an organization feel able to challenge assumptions.
- You’ll learn what leaders can uncover by observing who asks questions, which questions receive attention, and where questioning quietly stops within the hierarchy.
- Hear how to distinguish functional questions that help operate the business from larger questions that can reshape its strategy, direction, and future value.
- You’ll discover why intellectual humility does not require leaders to minimize their expertise, but does require them to recognize when that expertise may no longer fit the situation.
- Hear how “quieting your cleverness” and “listening atmospherically” can help experienced executives notice context, signals, and perspectives they might otherwise miss.
- You’ll learn why AI’s reliance on historical patterns makes human questioning especially important when technologies, markets, and customer expectations are changing.
- Hear how forward-looking reflection can improve future judgment rather than merely helping leaders interpret decisions they have already made.
Connect with Larry Robertson
Larry Robertson Website
Larry Robertson LinkedIn
Connect with Mahan Tavakoli:
Mahan Tavakoli Website
Mahan Tavakoli on LinkedIn
Partnering Leadership Website
