Innovating Out Loud with Larry Robertson

We take a lot for granted in innovation. Chief among them: that questions are where it all starts. So this episode, Larry Robertson and I decided to poke at our own assumption and see if it held up.Larry’s an innovation advisor and the author of Great Question, a book he built by talking to more than 140 people — neuroscientists, teachers, artists, CEOs. What he found is that we’re a questioning species. Our brains actually do their best work in uncertainty, not away from it. We got into why “best” isn’t a fixed answer but something you build together, why asking “why” too early kills the good stuff, and how I once flipped a data center project by asking “What if communities asked us to build one?” instead of “How do we get permission?” We closed on AI — useful, but only if you’ve already got the muscle it can’t teach you. An hour in, our assumption held. Questions really are where it starts.Five things worth carrying with you* Questions aren’t a technique. They’re how we’re built. Your brain does its sharpest thinking in change, complexity, and uncertainty — Larry’s neuroscientists call it “innovation mode.” So questioning isn’t something you bolt onto the work. It’s the work.* Quit leading with “why.” Start with “why” and you’re down a rabbit hole you won’t climb out of. Try Deb Meyer’s five instead: How do we know what we know? Is there a pattern? What if? Is there another way? Who cares? As Larry put it, a question is just going there. You’re not committing to anything yet.* Flip the question and watch the whole thing change. For years the industry asked, “How do we get permitted to build a data center?” We asked, “What if people were asking us to build one?” You can’t solve that the same way. What came out didn’t look, sound, or run like a data center at all. Because innovation is value creation — if it’s not changing someone’s life, it’s just a cool idea.* It starts with trusting yourself. Every field Larry studied circled back to the same thing: faith in your own questioning, earned from the wins and the flops. You can’t build that trust across a team if it isn’t there in you first. When you’re stuck, lean on the three things you can always trust — curiosity, play, and search.* AI can’t teach you to question. It can help. But AI averages toward an answer, and you can’t amplify a skill you don’t have. Build the muscle yourself, and how you use AI will change. Skip that, and you’re just handing over the thinking that would’ve made you better.You can find Larry’s book, Great Question: The Art of the Ask and Getting More of What Your Really Want everywhere books are sold.Next up on Innovating Out Loud: Angus Fletcher. Story Scientist and author of books that have come up in many previous episodes. Wonderworks and Primal Intelligence live on my desk. This is a not to miss session. NOTE the change of time: 10:30 AM PT / 1:30 PM ET. July 23, 2026. Register here and see you then! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com