The Power of How and What and the Weakness of Why Questions

Excerpted with permission from “Ask Powerful Questions – Create Conversations That Matter” by Will Wise

Recently, I found myself sitting in a fancy corner office, leading an energetic coaching session with an executive who had just shared that he’d said something to his boss and was now wondering if his words had been a mistake. I responded: “Why did you say that?” The conversation screeched to a halt as he looked at me with puzzlement, his forehead a mountain range of ridges.

Oops. I just made a mistake. Was it fixable? We had just been hitting a productive flow, but now it seemed like my client was getting defensive. He was about to exhale, lean back in his chair, and cross his arms (I had seen him do this before). “Wait just a moment, that was not a great question,” I said; “Let me rephrase. What compelled you to say that to him?”

His response was a complete shift. He exhaled, placed his hands on the table, and said, “I feel like someone should share with him the fallacy of his thinking.” Then he shared more. We were back in the flow.

How did one question cause him to nearly shut down? What happened with the next question that began to open him up again? Let’s look at which trap I fell into.

Trap: Asking Why questions thinking they are open

What is the question we ask most often when we believe we are asking an open-ended question?


While Why is considered an open-ended question, it does not elicit powerful and fresh answers.Why questions actually create defensive and scripted responses.

Think about times when someone asked you questions like these:

  • Why were you late?
  • Why did you do that?
  • Why are you wearing that?

What did you feel like? Most often, people feel defensive. When you have been asked these kinds of questions, do you feel the need to defend why you are late, explain your reason for doing something, or justify your choice in clothes? Do you think about anything new or just give the responses you have already considered giving?

Antidote: Drop the Why from your questions

If you find that people are responding to your questions with defensiveness or non-engagement, they may be reacting to your judgment. Although it is true that you can ask questions full of judgment that create defensiveness, that do not begin with “why”—especially when using a certain tone—a good place to begin the process of asking powerful questions is to drop the Why in your questions and see how people respond. Examine the following tool to replace the Why in your questions.

Tool: Powerful questions begin with How and What

Dropping the Why in our questions requires us to use something different to fill the void. Use How and What instead. Chances are, the heart of your Why question has some good material in it. So, drop the Why; use a How or What instead, and then do whatever is required to make the question make sense.

For example: Why . . . ?” becomes “What . . . ?”

Why did you go to the market when you had what we needed?” becomes “What compelled you to go to the market?”

Why are you wearing that?” becomes “What do you like about wearing that hat?” or “What is appealing about wearing that hat?”

Why were you late?” becomes “What happened?” or “What happened that made it difficult to get to work?”

Why . . . ?” becomes “How . . . ?”

Why did you do this?” becomes “How did this happen?”

Why do you charge so much?” becomes “How was this pricing structure decided?”

Why do you think like that?” becomes “How is it that you learned that?” or “How did you come to that understanding?”

You will notice that in the examples above, the words in the original sentence changed in order to make the question clear. You will do this naturally as you try to find ways not to sound judgmental.

When you create questions for which people will not feel the need to defend themselves, you will notice something else happening to your questions. The word “you” will show up less. The word “you” in a sentence may be perceived as a direct attack on the person (or persons) you are talking to, rather than what you are talking about. “Are we talking about ‘me’ or this thing around me?”

If you can begin to make conscious choices around using “you,” you will notice questions that are more powerful in your life. For instance, let’s look at a question in three iterations:

First, “Why did you complete that so fast?” 

This question is filled with judgment and the person will need to defend themselves, proving both the outcome and the process of how they got there.

Second, compare the first question to “How did you complete that so fast?”

Here the question is being asked with curiosity, about an observation you’ve made. The person can answer by simply explaining what they did (maybe they developed a shortcut!). They still may need to defend, depending on your rapport, because the presence of the word “you” might confuse and lead them to believe that they are being attacked.

Third, compare the second question to “How was that completed so fast?”

Now the question is about the process and not about the person. There is less to personally defend against. There is much more to talk about now, and the focus can be on the process and how it was different than before. This will happen naturally, as you drop the Why and attempt to create less defensiveness.

I suggest not focusing on the “you” component at first. That is a lot to think about. First, work on dropping the Why. That is enough of a mind workout to start with.

Dropping the Why from our questions requires us to think differently. We need to translate our Why questions into How or What questions. If your mind is anything like mine, this will give your brain a real workout. It is not easy because we have many years of practice in Whys, but the payoff is great. It is worth your time and effort. However, if you don’t believe me, go practice and see for yourself.

Note from Bob:  “Ask Powerful Questions: Create Conversations That Matter” was a page-turner for me.   If you are committed to growing as a Leader who “Leads With Questions” you will want to purchase your book today! 



Will Wise


WiLL WiSE, M.Ed., has over two decades of experience custom building leadership programs for corporate and nonprofit groups. Leaders call Will when there is a lack of trust getting in the way of results. Tens of thousands of people have been empowered with positive communication skills after spending some time with WiLL and We!™ Most recently, WiLL has been passionate about sharing his #1 Amazon Bestselling Book, Ask Powerful Questions: Create Conversations that Matter.


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