The Art of the Ask: How to Ask Better Questions
Quality answers come from quality questions, and quality answers can change the direction of your work or life. In this blog, Wonsupona gives tips on how to ask questions. Better.
branding, wonsupona, copywriting, questions, psychology,
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The Art of the Ask: How to Craft Better Questions


The Art of the Ask: How to Craft Better Questions

Photo by Caleb Ralston

Photo by Caleb Ralston

It has been said that if you ask a question in the right way, you can get anything you want. Isn’t that an incredible power?


Questions help expand our awareness and understanding of ourselves and the world. If you think about it, almost everything we want in life is the result of asking questions. Relationships, communities, and businesses are founded upon the answering and reflection of questions.

“Judge a man by his questions rather than his answers.” – Voltaire

The ability to ask questions, and more specifically, ask for what you want, is a skill few have mastered. When it comes to branding and storytelling, asking rich questions leads to deeper insights that can transform an entire strategy. When it comes to managing employees, questions can replace critiques, contributing to a more positive work environment. Of course, there’s a science behind asking the right questions.

“Where we are in our lives at this very moment, is very much a direct reflection of the questions we have habitually and unconsciously asked ourselves over time.”- Adam Sicinski

The Psychology of the Ask
My dear friend Linda told me that “the way you word your question determines how much you’re willing to hear.” Quality answers come from quality questions. So without further ado, here’s how to ask questions. Better.


Be Specific

“What are you thinking?” is an example of an open-ended question that is too broad and intimidating. Instead, add another layer of detail to open-ended questions. “What do you think about the 49ers winning the SuperBowl this year?” This particular type of layer is husband tried and true.


Avoid Yes or No Questions

When possible, avoid direct questions (yes or no) as this triggers the fight-or-flight reflex in brains of both the interviewer and the respondent, leading to anxiety.


Frame Questions in Terms of Solutions

We essentially eliminate all possibilities of answers that are not consistent with questions. By asking questions that are framed around exacerbating a problem, we become blinded to the solutions. Frame questions in terms of solutions. “What must we do now in order for this project to be a success?”


Experiment Replacing “Why” with “How”

Many ‘why’ questions can be weakening, leading to limitation, confusion and doubt. ‘How’ questions and ‘what’ questions can contribute to more solution-oriented answers. “How can we phrase this message to communicate a feeling of comfort?”


Aim to Empower

Questions formed in terms of accusations create walls, make people defensive and most likely, receive distorted answers. Empowering questions enable you to create a deeper connection with the other person, enabling a more honest response.


What new questions do you now seek answers to? If there’s a something missing in your life, look deeper, ask new questions and reflect on them. No doubt you’ll get different answers that will lead you a new way.


What’s the best question you’ve ever been asked? Write your response below!

  • Linda

    My most interesting question: What do you know that if the whole world knew, you would be relieved?

    October 12, 2015at6:39 pm
  • wonsupona

    Wow, what a great question! I’ll need to think about how I would answer that.

    October 12, 2015at7:08 pm
  • Anonymous

    Where were you before your parents were born?

    February 4, 2016at9:59 pm

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