Curated Questions: Conversations Celebrating the Power of Questions!

Ken Woodward built this entire show around a single premise: the questions we ask matter more than the answers we get. And honestly, he makes a convincing case for it. Each week he sits down with someone from a different field — entrepreneurs, academics, therapists, artists — and the conversation centers not on their accomplishments, but on the questions that shaped their thinking. It’s a subtle shift from your typical interview podcast, but it changes everything about how the conversations unfold. You get guests talking about the question they wished they’d asked ten years earlier, or the one that completely redirected their career. The show has about 78 episodes and updates weekly, with a perfect 5-star rating on Apple Podcasts (though from a smaller listener base). Episodes typically run around 40 to 50 minutes. Ken’s interviewing style is patient and curious — he doesn’t rush to the next topic, and he’s comfortable with silence, which lets guests think before they speak. Recent episodes have covered everything from the questions we never asked our grandmothers to how leaders can use inquiry to build better teams. If you’re the kind of person who thinks about metacognition or gets excited when someone reframes a problem you thought you understood, this show will feel like it was made for you. It’s less flashy than bigger podcasts in this space, but the quality of conversation is consistently high.