Six Questions You Should Never Ask

John R. Stoker is the author of  “Overcoming Fake Talk” and the president of Dialogue WORKS, Inc.  His organization helps clients and their teams improve leadership engagement in order to achieve superior results. He is an expert in the fields of leadership, change, dialogue, critical thinking, conflict resolution, and emotional intelligence, and has worked and spoken to such companies as Cox Communications, Lockheed Martin, Honeywell, and AbbVie. Connect with him on Facebook, LinkedIn, or Twitter. 

When I was just beginning my corporate career, there was a manager in our department that everyone referred to as the “Why-man.”  He didn’t understand the proper use of the “5 Why’s” tool which has the purpose of diving deeper in root-cause analysis.

Rather, his “why’s” were used to demean, not to seek understanding. He would ask such questions like, “Why did you do that?” “Why did you think that would work?” “Why did I ever believe you could do this?” or, “Why didn’t you check with me first?” There is nothing inherently wrong with asking “why” questions, but when using a sarcastic, cynical, or demeaning tone like he did, the underlying message is, “You’re an idiot.”

It’s also important to distinguish between “why” and “what” questions and the results of each. Asking “why” questions forces the listener to reflect on the past and to defend their actions or thoughts. For example, if you are asked, “Why did you do that?”, notice that this prompts you to remember what happened in the past, recall what you were thinking at the time, uncover the motivation behind your actions, and then formulate an answer that is reasonable, rational, and acceptable to the person asking the question.

I have found that asking “what” questions are generally more effective in eliciting productive responses. “What” questions are not only more neutral in their effect on the individual, but they can also be used to move a person into the future.

Asking “why” questions forces the listener to reflect on the past and to defend their actions or thoughts.


Let’s suppose a person did as you asked and their performance didn’t yield the desired results. They know the results of their actions didn’t meet your expectations, so it’s important to ask the right question to avoid defensiveness and excuses in their response. Rather than ask a “why” question which will likely not prompt the reply you are looking for, you could ask, “What did you learn?” to explore their understanding. Or, “What would you do differently going forward?” Notice in this instance, your question will move the person to reflect, discover, and project into the future in order to formulate their answer. Their response to such a question helps you to understand their thinking process and what might have been done instead to yield a better outcome. Rather than making someone feel attacked, this type of question is motivational and helps people want to improve. This is vastly different than asking questions that are demeaning and may not result in a truthful or beneficial response.

In addition to avoiding “why” questions, here are six common examples of questions not to ask.

“Were you even thinking when you did this?” This question is an attack on the person’s judgment. It is really nothing more than saying, “You obviously weren’t thinking when you did this.” Such a question is not a discovery question but is a disguised “tell”—a statement disguised as a question. This question forces the person to rehearse what they did and prompt a defensive response, reinforcing the negative rather than inspiring positive change. What might be more effective is to simply ask, “Help me understand what you were trying to achieve.” or, “What was your rationale for taking this course of action?” would be a more productive course to take.

“Will you ever be finished with that?” This question serves to criticize the person who is undertaking a task. It also carries the assumption that the person can’t be counted on to meet their commitment. How is a person even supposed to answer such a question? Any answer they give, such as, “It is taking longer than we had forecasted,” is unacceptable because the deadline may have already passed. This question really makes the point that the person is failing or is not meeting expectations. How much more effective would it be to simply ask, “Can you give me a concrete completion date for the task?” This kind of question requires the person to think and analyze what would be required to meet the deadline. It may also result in an open dialogue about issues that need to be considered to ensure timely completion.

“Don’t you think you should have…?” The purpose of this question is to give advice. The way this question is framed forces the person who responds to say something like, “Well, I guess I should have….” Most people would never counter their leader by saying, “No, I didn’t think I should have….” This “should” question is really nothing more than a statement of, “You should have ….” If you really want to understand a person and how they are viewing an issue, notice how much more powerful it is to ask, “What do you think you should do?” This is an open-ended question that inspires reflection and thoughtful response which is exactly what you want to take place.

“Were you the one who did this?” If the person who asks this question knows for sure that the other person did what they did, then the question serves nothing more than to emphasize, “I know you did this and you blew it.” This question serves to assign blame. Such a question does not seek understanding, clarity, or learning. Its purpose is to accuse, blame, and belittle.

“Didn’t you know that…?” This question is about making a point. Obviously, if someone did the wrong thing, they didn’t know what they should have done, or they wouldn’t have done it. People will typically respond, “No, I didn’t know that.” It is a way of making the person admit what they didn’t know, or it may encourage the person to blame someone else to avoid the consequences. In asking this question, the questioner misses the opportunity to learn what the person did or didn’t know and what they were hoping to achieve by their actions.

“You did what?” This question forces the person to self-justify their action or thinking. The person and the questioner obviously know what the person did or they could make mention of it in a question. Such a question serves to criticize the individual. It forces the person to identify their thinking in a forced admittance that they did the wrong thing. Rather than asking this question in a calm, respectful manner, it is usually asked in anger and frustration because of the lack of results. Again, the person answering the question may go so far as to justify their actions rather than assess and make improvements in the future.

These questions are usually asked out of frustration, and they will not help you get the answers you seek. Such questions tend to be disrespectful and demeaning, especially as they are usually accompanied by a negative tone and motivation. Unfortunately, all of us have likely either asked or been asked these types of questions. One of the easiest ways to create respect with others is to ask questions that will let the other person know that you are trying to understand and support them. Asking the right questions takes deliberate, thoughtful effort on your part. Taking the time to formulate and craft effective questions will help you get the answers you seek, increase rapport and respect, and improve your personal and professional results.

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