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Asking the Smart Questions: A Lesson for Success

by | Lifestyle

Voltaire got it right when he said, “Judge a man by his questions rather than by his answers.” In mentoring, as in life, asking questions is the primary way we learn to do better and be better. Questioning things we don’t understand is the most effective way to enhance learning, develop critical thinking skills, and build trust between the question-asker and the question-answerer. The key to success, however, is knowing when and how to ask the right questions. It’s knowing that while it may be true that there is no such thing as a stupid question, there is such a thing as a smart question. So yes, some questions are better than others, and those who ask smart questions are more likely to be the best at what they do because they learn in the best possible way as well.

But what makes a question a smart question?

First off, it is a question asked with intention. It is directed at understanding a specific goal, concept, or idea and is asked in fine detail. It is well-informed and relevant in such a way that it does not sound willfully ignorant. Does this mean you must be an expert to ask a question about a specific idea? No, but it does mean that you have to have done your homework. You have to have researched the information enough to understand the basic foundation of your question so that it is coming from an analytical perspective. A smart question may be framed with the phrase “Can you explain more about X, so that I may better understand Y?” You should know exactly the kind of information you are looking for so that your question creates clarity and you don’t end up with an open-ended answer.

A smart question is also not laced with judgment or asked in a condescending or undermining manner. It should be founded in facts and respect and asked out of honest curiosity. Smart questions express a certain level of empowerment and ownership towards the person to whom you are directing your question. For instance, “Based on your experience, what do you think is the next step?”

More than anything, a smart question is one that is asked to learn something you didn’t know before, and it is asked in a way that acknowledges the ideas and opinions of others. It offers thought and a fresh perspective and encourages others to see things in unpredictable ways. It pushes others to think critically, analytically, and creatively in hopes of provoking inner reflection. For example, consider asking something along the lines of “What did you learn from previous trials that made this one successful?”

As all things in life, timing is everything and asking a smart question is no exception. Make sure to consider the timing and relevance of the conversation and ask your question in a way that further encourages or propels the discussion forward.

By following these guidelines to ask the smartest question, you are ensuring the smartest response.


  1. Kyle Gatchalian

    Great article on how questions can be used for connecting and equipping.

  2. Megan T

    “More than anything, a smart question is one that is asked to learn something you didn’t know before, and it is asked in a way that acknowledges the ideas and opinions of others.”
    So good! A true spirit of humility. I know how amazingly valued and acknowledged I’ve felt when others have asked me questions like this. Thank you so much for breaking it down in such a way that I can learn to do it myself as well!

  3. Alan Escalante Lopez

    This is really helpful! I’ll definitely apply these principles. Thanks for sharing.

  4. Michael Steinberger

    I enjoyed this lesson. Like John Maxwell says, questions are like keys that open different doors!

  5. Leslie

    Great perspective and wisdom as usual. Thank you!