The Questioning Technique Every Student Should Know
Instead of teaching children the answer, we should teach them the questions.

Early in my career, I was mentored in a most amazing way by my boss. I was assigned to a project. I was young and precocious-confident in the planning skills that had already brought me success in school and my career up until that point. I am sure my boss saw my naivete. He had more than a couple of decades of deep experience in project management. Here is what he told me as I remember it:
“Rebecca, the best way to manage a project is to start with five basic questions. You should always know who, what, when, where, why, and how. Remember five ‘W’s’ and one ‘H.’
I didn’t learn until much later in my career that more than 70% of all projects fail. I didn’t quite understand way back then that there is a BIG difference between achieving individual success and creating team success.
That first project didn’t go so well. Unfortunately, I used an individual approach and ended up alienating most of my team. I got the job done, but it was at much personal expense. I ended up doing most of the work myself.
After receiving additional training in project management, the approach that my boss shared with me kept showing up repeatedly. As I reflect on it now, I wonder, “Why didn’t they teach me that in school?”
The new world of work is very different from the one that ushered in the Industrial Age. As people left farms to go work in factories, the skills they possessed by managing farms were somewhat transferrable. And most companies invested time and money to train the incoming workforce.
Fast forward to the 1940s, and the trend began to shift. The age of science and engineering miracles demanded a new kind of worker-one who could think on their own. While school systems continued to produce students ready for a manufacturing environment, one that was structured and led by expert managers, the demand for “knowledge workers” slowly rose. Manufacturing plants in America began to disappear. But we didn’t see the effects of it until early in this century.
Between 2000 and 2010, US manufacturing experienced a nightmare. The number of manufacturing jobs in the United States, which had been relatively stable at 17 million since 1965, declined by one third in that decade, falling by 5.8 million to below 12 million in 2010 (returning to just 12.3 million in 2016).
William B. Bonvillian Lecturer at MIT and Advisor to MIT’s Industrial Performance Center
And here we are in the Information Age where technology and innovation are primary drivers of business success. Companies are no longer creating mass training programs. Workers must be ready to work when they enter the door. This has driven companies away from hiring inexperienced workers who can’t understand how to work in this new environment. The result is many college graduates who can’t seem to get their foot in the door of corporations in need of ready-to-work talent.
All of this is important to understand because it is the backdrop for why we must teach our children differently. The 21st century is demanding a new kind of worker.
As a scientist, I was trained to ask two questions consistently: “Why…?” and “How…?” As my story in the opening paragraphs points out, those two questions alone were not enough to help me manage my project.
What I learned as I matured in my career is the importance of asking the right questions. As I grew in my skill, people began asking me, “How did you get that information?” It was really simple. I asked the right questions.
So, I will outline the value you can give your students as you teach them the power of the “Five Ws and One H.”
Ask “Who?” This question seems rather basic, but I am amazed at how many people miss the opportunity to clarify the “who.” I hear people say “they,” “them,” “most people,” etc. And no one bothers to ask, “Who are they?” “Who are them?” “Who are most people?” In fact, I have found when people use these phrases, they often mean “I” or “me.” Using these other terms is a way to deflect the fact that they want you to believe that others believe the way they do. Or if they are talking about a real person, you will discover EXACTLY who. Always ask, “Who?”
Ask “What?” This question can go in all kinds of directions. This question, married to the “Who” question, will get to the essence of what you need to know. As our English teachers taught us when writing a clear sentence, first identify the “who” or “what.” Yes, we should do that beyond English class. “What does that mean?” “What are we doing?” “What is the main point?” There are so many options for what questions but use judiciously. In conversation, it can cause you to veer off-topic. Always ask, “What?”
Ask “When?” There is a quote, “Timing is EVERYTHING.” And when you enter the workforce, timing and time become the primary drivers of success. A great product delivered too late can cause hundreds or thousands of dollars to be lost. People in the workforce must always know “when.” But what happens when your boss gives you an assignment and fails to mention when it is due? Unlike school teachers who make the “when” very clear, sometimes the worker is left with the task of clarifying the “when” on their own. I learned this the hard way. Assigned a task to complete, I added it to my “To Do” list for next week. When the boss came back the next day ready for my results, a blank stare ensued. I forgot to ask him, “When?”
Ask “Where?” I call this “The Differentiator Question.” In Kepner-Trego problem-solving, you are taught to ask two questions:
- Where does this happen?
- Where does this NOT happen?
If I told you, “Gravity does not exist,” I would suggest you ask me “Where?” before testing it here on Earth. Knowing “where” will give you all kinds of information that you might not otherwise discover. Always ask, “Where?”
Ask “Why?” Of all of the questions, the “Why” question must be used sparingly. Asking “Why?” can be interpreted offensively if used in the wrong situation or at the wrong time. I would recommend these alternatives to ask, “Why?”:
- Describe that for me.
- Can you help me understand the reason behind that?
- What makes that work?
Using this question has helped me find people with hidden expertise in certain subject areas. It has also help me uncover the details behind what people think so that I can make better decisions. Always ask, “Why?”
Ask “How.” Of all of the questions, this one is my favorite. I often ask:
“How does that work?”
What follows is usually a fascinating conversation in discovery. This question helps me bring to light and validate who holds expertise. If you can’t explain how it works, you probably don’t understand it. And if the person doesn’t know, I have found that it often leads to a referral to someone who does know “how that works.” It’s a great question to use when you want to understand, validate information, or find a subject matter expert. Always ask, “How?”
How might you use this to create an activity for your class to discover this powerful questioning technique?
I would love to hear what you create.
