How Do You Respond to Challenging Questions?

Children can sometimes question endlessly, can’t they? They have been known to ask what something is, and then when you explain it, they may ask “Why?” over and over to try to learn more deeply.

As adults, we have often reached a point where we stopped questioning. This is unfortunate as I can see that this habit of not questioning has taken a toll on society.

On a routine basis in my interactions with experts, I will ask a question that could be challenging – for example, it could be unique or considering things from a different perspective. Usually, I feel that they should know the answer because I am asking an expert in their field. I feel that I am just asking them to think through problems in a slightly more complex way, rather than just giving me the solution they may find in their work manual or a Google search.

Often when I ask these questions, I am met with some of the following responses:

“I’m really not sure – maybe the reason is...”

When I hear this, usually they make something up, where often it is obvious to me that their answer is not correct. The problem with this approach is that they are more concerned with appearing to be helpful rather than actually being helpful. Sometimes, I also have the impression that they are worried about looking foolish or unknowledgeable – they want to hide the fact that they do not know certain things. With their approach, they are not learning anything new from my questions.

“I have no idea. That isn’t what we focus on here.”

Often, they will tell me this in an annoyed tone, as if I shouldn’t be asking questions. The problem here is that I have asked a question somehow related to their field. Yet, they are drawing clear lines as to what they will not think about. With that approach, their knowledge will forever remain limited as they refuse to learn new things. I understand that some things are outside of a person’s professional domain, but I still think people should be more curious about how different domains are related. Divisions between fields are often just imaginary lines or boundaries that we draw. In reality, everything is interrelated.

 “What’s important actually is that….”

After saying this, they focus on something else, more concerned with selling a product or guiding me to do what they want me to do rather than answer my question. In this case, they do not place value on questions. They view questions as a distraction from meeting their goal. This is a mistake because if they actually learned how to answer some questions, they could better help their clients and better meet their goals. In this case, they seem to be refusing to acknowledge that anything they don’t already know could be important.

The above responses are the most frequent ones that I get. The ones below are less common.

 “That is a good question. I don’t know the answer, but I will have to look it up and get back to you.”

Although they probably have good intentions, they usually never get back to me. Usually, this is someone who is interested in learning or in helping their clients. Still, they are very focused on meeting their immediate goals, and they will probably not invest time in looking up answers unless they think it is necessary. Although this is better than some of the above options, they are still failing to learn from new questions that they receive. And most of the time, they have still not actually answered the question I presented.

“I will look this up now,” or “I will ask my supervisor and get back to you in a moment.”

Usually, with this approach, they can give me a helpful response. Typically, even if they do not know the answer, they can help me understand why they do not know. Perhaps they will explain that there are several possible reasons that something has happened. Or they may need to run extra tests or perform extra services to answer some of my questions. The person who responds with the above phrase (in bold) will place value on new questions and seek to answer them. They will understand that questions present an opportunity for learning and growth. This response is fairly rare, and I am glad to see that some people (or the organizations they belong to) value answering potentially challenging questions.

 

“The answer is:” (and they proceed to give a good and reasonable answer.)

This is the part that saddens me. When I ask unique, thoughtful, or detailed questions, I don’t expect to receive good answers anymore. This is because of my experiences in having seen that most of the time, I will not receive useful answers to my questions. Usually, I am met with one of the top 4 phrases mentioned above – which results in me getting no answers.

The person who knows the answer to my question right away usually has a lot of experience is highly talented, or places a lot of value on learning new things and trying to answer new questions effectively. Someone who answers my question with reasonable solutions has probably thought through this question already. They have been asked similar questions in the past, but rather than avoid the question, they learned what they needed to answer it appropriately.

With this type of person, sometimes I will continue to ask more questions. My curiosity is endless, and I am fascinated by the opportunity to learn more about topics from people who are truly experts in their fields. Often, someone who can answer one challenging question is also quite capable of handling other challenging questions. After a few questions, I will often get to a point where we find a limit to their knowledge. But this type of person will always think about my questions more deeply and seek the answers for their own benefit.

 

It is frustrating to see that many people on a daily basis are on autopilot. They are going through certain motions. They do not expect any challenges in their day, nor do they want them. Any new question is assumed to be pointless or a distraction. For many of us, we see questions as child’s play. We think of the child who annoyed us with endless questions, or the person who makes a fool of himself asking questions with obvious answers, or we think of the teacher who scolded us for “wasting” classroom time with questions. Questions have a bad reputation for many of us, but we need to focus on bringing them back into our lives.

In my life, questions are the primary thinking tool I use for everything. The trick isn’t just to ask questions but to ask good ones. How do you ask good questions? By developing the habit of questioning so that you learn to ask better and better questions. What is a good question? The good question is that which helps you to accomplish your goals.

I want to be challenged with new, interesting, and even difficult questions. Actually, I think we should all want this.  

Do you really want to think the same thoughts every day, do the same things every day, and not be pushed into becoming anything better every day?

Is that what we are truly after? This seems quite meaningless to me, as I hope it does to you as well.

Today, I ask you to challenge me, to push me further.

Ask me any question, even if you are sure I will not know the answer.

You can do so in the comments section below.

I am the type of person who cannot let it go. When I am asked something, it will roll around in my mind until I find a solution. If I go to sleep concerned about something, I wake up with the solution in my mind.

I cannot guarantee that I will know the answer to your question, but I will try to figure it out and give you a helpful response.

In your life, seek to ask more questions and encourage people to ask you more questions. When you are asked new and challenging questions, search deeply for the answers. You will become more and more confident every day in your ability to solve problems if you do this.


Eventually, you may reach a point where you can craft the right questions for yourself, and you can seek your own answers to these questions.


If you could use some example questions to help get you into the questioning mindset, consider reading the following (written with co-author Dave Edelstein):

Question Yourself: 365 Questions to Explore Your Inner Self & Reveal Your True Nature

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The Value of NOT Thinking