The Dumbest Question in the Room | Episode 01.05

One of Alessandra’s clients, a CFO who sits at the top of her field, calls the sharpest thing she does asking dumb questions. Alessandra refuses to let her keep that word. Derrick walks into the episode holding a question of his own. He spent the afternoon pressing prompts onto cards for an event where strangers sit down and talk for no reason other than the conversation, and he opens by asking Alessandra what question she has carried since childhood and never been able to answer. The thesis: a good question is an act of investment in another person, and the right one at the right moment can change how someone sees their own life.In this episode:* A CFO who calls her own gift “asking dumb questions,” and the reframe that turns it into seeing the blank spaces everyone else talks around* Why the people who are best at asking questions are often the worst at asking them of themselves.* Alessandra’s 3 categories of questions, from the surface ones that help you place a person, to the clarifying ones that gather data, to the ones that rearrange the furniture in someone’s mind.* Derrick’s afternoon in a mall behind a sign that read “free water and conversations,” and the stranger who offered eight minutes and stayed forty-five.* Questions Alessandra refuses to ask, and the lazy assumptions hiding inside them.* Derrick’s lifelong question, and the belief underneath it that one small overlooked thing can transform a person, a company, or a lifeThe challenge for you: Take a beat this week with a pad or a voice recorder and answer two prompts. * What are two questions you hate being asked? * What are three questions you love to ask or be asked? Notice what your answers tell you about what you value and how you want people to meet you. Then carry one of the questions you love into your next conversation and watch what it opens.Let’s Play is a podcast for serious and not-so-serious people doing big things.Hosted by Alessandra Wall & Derrick Yanford.Where to find Alessandra | Where to find Derrick Get full access to The Power Pause at drwallsays.substack.com/subscribe