What If Great Leaders Don't Have All the Answers? with Inbal Shani | #22

What if the best leaders are not the ones with all the answers, but the ones who know how to ask better questions? In this episode of What If?, Leslie Grandy sits down with Inbal Shani, Chief Product Officer and Head of R&D at Twilio, to explore what leadership looks like when curiosity, judgment, and experimentation matter more than certainty. Inbal's career has taken her from aerospace engineering and applied science to leadership roles at Amazon, GitHub, Microsoft, and Twilio. Across that journey, she has built a deep understanding of complex systems, not just how individual components work, but how they connect, interact, and create something larger together. That systems mindset shapes the way she thinks about product, culture, innovation, and AI. Together, Leslie and Inbal explore: Why great leaders do not need to know everything, but they do need to stay curious How asking questions can become a strength rather than a signal of insecurity Why failure only becomes valuable when teams communicate honestly about risk, blockers, and learning How leaders can create environments where experimentation is encouraged but not reckless Why customer problems should ground innovation, even when teams are building toward a future market What Inbal learned from the cancellation of the Amazon Fire Phone, and how that failure produced assets that later helped fuel Alexa and Amazon's last-mile capabilities Why innovation must happen across the whole company, not just inside isolated labs How companies get AI transformation wrong when they start with fear of missing out instead of purpose Why the better AI question is not "What is our AI strategy?" but "Where can better tools help this business operate more successfully?" Why AI should sharpen human thinking, not replace it Inbal offers a clear warning for this moment: when companies adopt AI because the board says they need an AI strategy, they often drive the wrong behavior. The technology becomes a mandate instead of a meaningful answer to a real problem. Purpose has to come first. That means understanding the customer problem, the employee problem, or the business friction AI is meant to solve before deciding how to use it. It also means refusing to outsource judgment. AI can accelerate work, help teams prototype faster, support engineers, personalize customer experiences, and reduce friction. But Inbal cautions against delegating the thinking itself. The human work still matters: curiosity, creativity, judgment, subject-matter expertise, and the ability to know whether an answer is merely adequate or actually great. This conversation is a reminder that leadership in an AI-accelerated world is not about pretending to have certainty. It is about building the conditions where people can ask better questions, fail forward, learn quickly, and use technology with purpose. Because the leaders who matter most now are not the ones who already know. They are the ones still willing to learn. Reflection question: Where are you looking for an answer too quickly, when the better leadership move might be to ask a more purposeful question?