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5 Ways to Ask Better Questions
“Did you enjoy the trip?” → Yes/no
“What surprised you about the trip?” → A story wants to emerge
Some open questions are still dead ends. Some closed questions crack people open. The real distinction: does the question invite a story or request a data point?
the full class
The question shapes the answer it receives.
Most questions close doors. A few questions open rooms. This class teaches five techniques for asking questions that make people want to answer — questions that go deeper, reveal more, and create connection instead of interrogation. One lesson per day. Each explains one move, shows examples, and gives you an exercise. You submit questions. You get feedback. By day five, you'll notice the questions that unlock people — and the ones that shut them down.
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I.Open vs. closed — and why it's not that simple.
You've heard “ask open questions.” That's not wrong, but it's incomplete. Some open questions are still dead ends. Some closed questions crack people open. The real distinction: does the question invite a story or request a data point?
“Did you enjoy the trip?” → Yes/no
“What surprised you about the trip?” → A story wants to emerge
exerciseTake five closed questions you asked recently. Rewrite each to invite a story instead of requesting data.
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II.Follow the heat.
When someone's voice changes — speeds up, slows down, gets quieter — that's heat. The question that follows should go toward it, not away.
“It was fine. Mostly. The part at the end was… anyway, we made it home.”
Most people ask “How was the drive home?” Follow the heat: “What happened at the end?”
exerciseWrite a short exchange where one person's response contains a flash of heat — a trailing off, a shift, an “anyway.” Then write three possible follow-up questions. Identify which follows the heat and which avoids it.
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III.The question you're not supposed to ask.
Most conversations have an elephant. The thing everyone's avoiding. Naming it isn't rude — it's relief. The skill is naming it warmly.
“Can I ask about the thing we're not talking about?”
Or, more specifically:
“You've mentioned the job three times without saying how it's going. Can I ask?”
exerciseThink of a real conversation where there was an elephant. Write the question you could have asked to name it without accusation.
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IV.Let them teach you.
People light up when asked about their expertise, their obsession, the thing they know that others don't. The question “What do most people get wrong about X?” turns them into the authority.
“You've been a nurse for twenty years. What do most people misunderstand about hospitals?”
Now they're teaching. Now they're invested.
exerciseWrite five “what do most people get wrong about…” questions for five different people in your life. Be specific to their actual expertise.
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V.The question that ends with silence.
The most powerful questions aren't answered immediately. They create a pause. The person looks away, thinks, comes back different.
“What would you do if you weren't afraid?”
“What do you wish someone would ask you?”
These questions don't have cached answers. They require real-time thought.
exerciseWrite three questions so genuine that you'd need to pause before answering them yourself.