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Better Questions Take Practice

Curiosity becomes useful when we learn to give it a clearer shape.

By Shane MurphyPublished 4 days ago • 3 min read

“Any questions?” often arrives at the exact moment when a person has not yet worked out what they do not understand. Silence follows, and everyone moves on. The silence may mean agreement. It may also mean that the available question is still a blur.

I think asking questions deserves deliberate practice. We often treat it as a personality trait: some people are curious, confident, or naturally good at conversation. Those qualities may affect how readily someone speaks, but they do not settle whether the question they ask will help. A question can be revised like a sentence.

Consider a hypothetical discussion about a new booking form. “Will this work?” invites a broad reassurance. “What happens when somebody tries to book two overlapping times?” asks for a particular behaviour. The second question is not more intelligent because it is longer. It gives the conversation somewhere definite to go.

A useful practice begins by writing down your first question privately. Then identify what you actually want to learn. Are you checking your understanding, looking for a missing condition, exploring an alternative, or asking someone to explain their reasoning? Different purposes call for different shapes of question.

If you are checking understanding, offer a brief account that can be corrected. “Have I understood that people can change their booking until the day before?” is easier to answer than “Can you explain it again?” The broader request may sometimes be necessary, but the specific version shows where your current understanding stands.

If you are exploring reasoning, avoid smuggling an accusation into the wording. “Why did you ignore the simpler option?” assumes both neglect and simplicity. “What led you to choose this option over the other one?” leaves room for information you do not yet have. You can challenge the answer afterward without forcing the opening into a defence.

Another practice is to remove the answer you have hidden inside the question. “Wouldn’t a shorter form obviously be better?” is mostly a statement seeking agreement. Try, “Which questions on the form are necessary to complete the booking?” This allows the discussion to reveal whether shortening it is useful and where it might cause trouble.

Good questions also have an appropriate size. “What should the whole experience be?” may overwhelm a conversation intended to settle one screen. “Which details does someone need before choosing a time?” is a smaller doorway. A narrow question is not automatically timid. It can uncover a concrete dependency that a sweeping conversation would miss.

Practice listening to the answer before preparing your next intervention. This sounds obvious, yet a beautifully phrased question is wasted when it is merely the preface to a speech. A useful follow-up often borrows a word from the answer: “When you say flexible, do you mean people can change the time or the number of attendees?”

There is also discipline in deciding when not to ask. A question should not be a way of transferring every small effort of understanding to somebody else. Reading the relevant paragraph or trying the obvious control can produce a better question afterward. Preparation helps distinguish an actual uncertainty from a detail that was already available.

For a small exercise, take one recurring conversation and revise a single question before entering it. Afterward, note whether the answer clarified the issue you intended to explore. If it did not, ask whether the question was too broad, assumed too much, or addressed the wrong person. Treat that as feedback on the wording, not a verdict on your character.

The ambition is not to become the person with the cleverest question in the room. Questions can be used to display knowledge, corner a speaker, or delay a decision while appearing thoughtful. Better practice aims elsewhere: towards making uncertainty easier to name and shared understanding easier to build. The question succeeds when the conversation can move somewhere useful because it was asked.

It is worth practising with ordinary subjects, where the pressure to sound impressive is low. Ask what made a recipe difficult or why a route felt confusing. These small conversations give you room to notice whether your wording invites a useful answer.

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About the Creator

Shane Murphy

Shane Ian Murphy: co-founder/partner, Tri-Party Tokenisation; founder/CEO, Global Secure Technologies (planned 2027 launch); co-founder/partner, Dual Party Capital. Partner, RougeN International Corp. Formerly of Limitless Mobile.

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    Written by Shane Murphy