Asking Great Questions

Mike Presley
7 min readApr 27, 2016

In 1973, a middle aged man changed the world…

Martin Cooper, a seasoned engineer in mobile communications, was asked by Motorola to develop the next generation of car telephones. He jumped at the offer…but not the challenge. Instead, Martin took a step back and paused. He started questioning car phones and communication, and eventually asked one of the most important questions of the last 43 years:

“Why is it that when we want to talk to someone, we have to call a place?”

This question completely changed the direction of his project and allowed Martin and his team to re-focus their attention on the true goal at hand— Disconnecting a human from a place.

It was his intentional pause and deep inquiry of the problem that allowed Martin to shift his efforts from creating a better car phone, to fixing the core problem with telephone communications — being attached to a location. His redefined project lead to the birth of the cell phone and the first (public) mobile phone call in history.

Look Ma…No wires!

Martin understood that to solve great problems, you have to ask great questions. You can’t make assumptions and jump in feet first.

A study by O.C. Tanner Institute, found that by asking the right questions your work was 4.1 times more likely to create a positive effect on others, 3.1 times more likely to be viewed as important, and 2.8 times more likely to create passion in the creator. They also found that it was 2.7 times more likely to positively impact on the bottom line!

So, what are bad questions and what are good questions?

I truly believe that there are no stupid questions. However, in the context of creativity and design thinking, there are some questions you should focus on and some you should ignore.

Bad Questions

Bad questions are any question that inhibits the responder’s answer or encourages them to answer in a specific manner. Typically, these fall under two categories: Close-Ended or Leading.

Close-Ended Questions

These are questions that can be answered in a single word or with a short statement. They provide no effective insight and do not encourage discussion or free thought. These are usually Yes/No questions. For example, “Do you approve of the design options?”

Leading Questions

These are questions that point the respondent’s answer in a particular direction or that have an assumed answer built-in. Leading questions can be close-ended, but are more intentional. For example, “It looks like everyone on the team really loved the latest designs! Don’t you think?”

Good Questions

Good questions encourage intellectual thinking by the responder, allow for open-ended answers, and provide additional insight and depth into the issue. There are many different categories of good questions; however, there are four that really help draw out valuable insights from the respondent. These are: Clarifying, Adjoining, Funneling, and Elevating.

Clarifying Questions

These questions help uncover the real intent behind a statement or answer, and help you better understand what has been said. An example might be, “When you said you did not like the last design, what exactly did you mean by that? Can you explain further?”

Adjoining Questions

These explore related parts of a problem that may have been overlooked or missed during a conversation. These types of questions can help you take a step back and gain a broader understanding of the the problem and its surrounding issues. For example: “How effectively do you think this design concept will translate to mobile devices?”

Funneling Questions

Funneling is actually a technique used to dive deeper into how an answer was derived. It can be used to challenge assumptions or to understand the root cause of a problem. To perform, you start with a broad question and refine your follow-up questions based on answers you receive until you find the root cause. This type of questioning is used a lot in detective work. An example might be:

“Which concept did you prefer, 1 or 2?”

— Concept 1

“Can you tell me more about why you liked Concept 1?”

— The color palette and overall flow.

“Which parts of the flow were your favorite?”

— I loved the guidance and the immediate confirmation!

Elevating Questions

These questions touch on broader issues and focus on the bigger picture at hand. While similar to adjoining questions, elevating questions are used to zoom out from the specific issue and see the overall context around it. An example of this is: “How will the latest designs affect the overall branding and marketing strategy of the company?”

source: HBR

But how do I ask GREAT questions?

Great questions are not something you ask, but an intentional process that you follow.

The first step, and the most important step, is the Pause. When you are presented with a problem, your lizard brain goes into fight or flight mode, and you immediately start trying to solve the problem at hand. While this might save you for the moment, it will not help solve the underlying issue. Therefore, it is very important to recognize this and ignore your initial urge to jump right in and start working.

Instead, you should take some time to think about the problem and formulate your questions. Be intentional and respect this moment of silence. Take a deep breath and invoke your creativity and wonderment about why this is a problem in the first place. Invest the time you need to think about the problem and craft your questions.

“Effective discussion and learning comes from thoughtful and inquisitive questioning.”

Then, take note of your assumptions and turn them into questions so you can gauge their validity. Assumptions are like Wikipedia — by themselves they can get you in trouble, but when used as a starting point to build from, they can lead to some great findings!

It is easy to get caught up in the problem at hand, especially in a busy world; however, it’s when you stop and think about a problem that you start to gain insight that will lead you to the root cause.

Once your questions are ready, it is time to start inquiring. Edgar Schein has a great definition of inquiry in his book, Humble Inquiry: The Gentle Art of Asking Instead of Telling. He states that a:

“[Humble] Inquiry is the fine art of drawing someone out, of asking questions, to which you do not already know the answers, of building a relationship based on curiosity and interest in the other person.”

This definition is perfect because it speaks to the importance of empathy in problem solving, and it points out that good questioning is an art and is rooted in our genuine curiosity as humans.

Lastly, once you have received an answer, take the time to pause and ponder the answer. Formulate new questions based on this answer and then start all over with a new question. Repeat until you get to the root cause of your problem.

Pause, Ponder, Inquire, and Repeat. This process utilizes all four of the Good Question types, helps you avoid asking Bad Questions, and is proven to be effective in everything from problem-solving to quality management. It is simple but effective, and is the basis for Toyota’s 5 Why’s Technique — which states that by asking “why” no fewer than 5 times, the root cause, and usually its solution, will become clear.

This is great, but what’s in it for me?

Everything. Asking thoughtful and engaging questions will not only help you solve problems at work, it’s also a great way to cultivate your curiosity and creative thinking, connect with the people around you, and build true empathy for your world. This is why children ask “Why?” all the time. They are constantly trying to understand their world and build mental models of how things work. As adults, we tend to be hesitant of asking “Why?,” and we should not be. This is how we learn and grow.

Finally, by asking good questions, you are able to gain a complete understanding of the core reason for performing a task, chore, or project. You will know the consequences of doing, or not doing, something, and thus are able to focus your efforts on what is most important to you and your goals. Everything you do will have purpose and true meaning.

And when you truly understand and believe in what you are doing, you will always do your best work!

(100 Day Challenge #9 — 100 Days of Medium)

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