How to Ask the Right Questions Part 1: The Paradox of the Right Question and how to ask it
In my travels one of the more common questions from new and experienced business analysts is “how do I ask the Right Questions?” There seems to be a belief that expert business analysts have a knack for choosing just the Right Question that will produce the answers that will solve the problem. So I thought I’d write a short piece about asking the Right Question, primarily to remove the anxiety and concern business analysts seem to have about asking the right question. I discussed the concept with a couple of business analysts and during the conversation I realized that the problem was not in knowing what to ask, but rather in how to ask it. My short piece blossomed into a four-part article, first discussing the paradox of trying to determine the Right Question to ask, and tips on asking the right question. The second part addresses what questions to ask to make sure you ask the Right Question. The third part focuses on how to ask the Right Question to get the right answer. And the fourth part deals with avoiding asking the wrong questions, or more specifically asking the Right Questions in the wrong way.
The Right Question. It conjures up a image of the business analyst spends time preparing a list of questions, and agonizing over each one to determine whether this one question is the Right Question for this particular stakeholder at this time in this specific situation.
With that kind of pressure on the business analyst to be sure to ask the Right Question, no wonder one of the business analyst’s more frequent questions is “how do I ask the Right Questions?” The issue is never “how do I ask questions?” but always about the “Right Question“. So let us talk about the Right Question and how to track it down and ask it.
Why is it so important to ask the Right Question?
First of all we need to understand that questions are the mainstay of the business analysts’ process. The business analyst lives on information. The more information the better. The business analyst needs information in order to analyze. The analysis of the information is what produces the problem, the solution, the requirements, and the results. And information is acquired by asking questions: first, of yourself, and then of others.
So what is a right question? As with many things in life. One of the better ways of determining how to excel in a particular area of expertise is to see how those we consider to be experts do it. I have mentioned Sherlock Holmes in the past as a model for business analysts in terms of critical thinking and analysis, but Sherlock Holmes was also a consummate interviewer. He not only gathered information with his magnifying glass, microscope, and keen eye, he also questioned witnesses and his clients, not to mention the perpetrators. A classic plot pattern that apparently started with Conan Doyle has Sherlock Holmes apprehending the culprit and then asking the wrongdoer to explain the details of the crime. This begins an description occupying a good portion of the book or story explaining all the details of Mormon revenge (A Study in Scarlet), stolen treasure (The Sign of Four) and so forth.
Perhaps a more current and non-fictional model for asking questions might be better for us to understand what the Right Question is. David Frost and Barbara Walters are examples of people paid lots of money to ask the Right Question. There are also print journalists of note who break stories by apparently knowing the Right Questions to ask.
So why is there such a focus on asking the Right Question? Perhaps because the literature seems to indicate that there are Right Questions out there floating around and the business analyst simply has to grab one and ask it. For example, the lead sentence in an article written in 2011 by Wilco Charité titled “Asking the Right Questions: Process Discovery” says, “If you are an internal Business Analyst or consultant asking the right questions in a Discovery project is a critical skill.” 
And there are further exhortations from various people of note: Actress, activist, and author Vanessa Redgrave says, “Ask the right questions if you’re going to find the right answers.” Entrepreneur Robert Half says, “Asking the right questions takes as much skill as giving the right answers.” And anthropologist, Claude Levi-Strauss suggests: “The wise man doesn’t give the right answers, he poses the right questions.”
Perhaps the belief that there is a Right Question comes from the many lawyer shows in which Perry Mason or Jack McCoy (Sam Waterston in Law & Order) always seem to ask the question which causes the person on the witness stand to break down and confess the murder or say some incriminating statement that turns the case around. Or the detectives like Miss Marple, or Hercule Poirot, or Columbo, who seemed to be able to ask the Right Questions that produces an rendering of the crime and catches the perpetrator.
And how does the concept of the Right Question affect the business analyst?
Even when a business analyst feels as though they have done a particularly effective job of elicitation, and have all the information that defines the problem and / or solution, there are “surprises” that crop up after the elicitation phase is theoretically done. And that is when the business analyst commiserates with other business analysts saying, “They didn’t tell me about that! If only I had asked the Right Question!” Business analysts need to get information and it seems that sometimes only the Right Question will get that information.
What is the Right Question?
So with all this concern about asking the Right Question, perhaps we should determine what a Right Question is.
Trying to figure out the Right Question to ask is a paradox. You cannot know if you’ve asked the right question until you have received an answer. If the answer to a question gives you the information that you are looking for then you have asked the Right Question. But you only know that it was the Right Question after the information gathering session is over and you have analyzed the results. And if you ask many questions to get the information you are seeking, how do you know which one is the Right Question?
So, what is a Right Question? The Right Question is the question that gives us the Right Answer. We may never really know what the Right Question is. Only the Right Answer is important.
For example, in perhaps the greatest interview of the 20th century, David Frost got former president, Richard Nixon to say, “I let down my friends. I let down the country. I look down our system of government and the dreams of all those young people that want to get into government, but now think it too corrupt. I let the American people down and I have to carry that burden with me the rest of my life.” This answer has been quoted and referred to many times and is the climax of the stage play and movie “Frost / Nixon”. But does anyone remember the question that preceded. Does anyone remember the right question? What remember is the right answer. And, in fact, that answer was the result of dozens of questions over several sessions, all asking for the same answer, which was finally given in response to just one question.
The bottom line: we can never really know we have asked the Right Question until after we have all the answers and analyze them to see if we now know what we need to know; we have the Right Answer. But, then, of course, you have to know what the Right Answer is before you ask the Right Question. And that might be the problem.
How do you ask the Right Question? Ask more questions
“Asking more questions reduces the need to have all the answers.”
Donald Peterson, former CEO of Ford Motor Company
The real answer to asking the right questions is simple: keep asking. When you ask enough questions, in and among all the questions you ask are the right ones. As long as you listen well and keep the focus on the problem or the solution, it does not matter which questions are Right. In the end, the Right Questions are those that get you relevant information. 
The only true way of asking the Right Question is to keep asking questions and asking more questions. The more questions you ask the greater the chances that you will get the answers that you are looking for: especially the Right Answer.
In addition to eventually asking the Right Question, asking more questions has the advantage of increasing the amount of information we as business analysts have to analyze, increasing our chances that we have found the Right Answer.
Consider our models, David Frost and Barbara Walters who always seem to ask the Right Question . What we see is not the full interview, but an edited version. The editors put the show together for entertainment, cutting out the questions that were not so Right, and adroitly placing the commercials right after a particular Right Question so that it will have the most memorable effect. To get the one hour dramatic interview with Prime Minister Tony Blair, President Richard Nixon, Michael Jackson or Jane Fonda, Frost and Walters had to prepare thousands of questions and probably ask hundreds. Many questions were pedestrian and many probably got answers that are not pertinent, or at least not entertaining or informative.
And those Pulitzer Prize winning journalists have reams of notes from hundreds of interviews consisting of hundreds of questions to produce a single news or magazine or article. A major part of a journalist’s work is the editing of the information gained from interviews and other information gathering into a cohesive whole
Business analysts do have a form of editing: it’s called analysis. The analysis is done after the information is collected, not before. We don’t analyze what we are going to ask so that we produce the Right Question; we just ask as many questions as we can and get as much information as we can so that we can determine the Right Answer afterwards. While there are techniques to getting more information, determining the Right Answer relies almost solely on the ability to analyze. More on this later.
How do I ask more questions? Redevelop Intellectual Curiosity
One personal characteristic that will help you ask the Right Questions is intellectual curiosity. When you can inculcate a desire to know everything about everything, questions, especially Right Questions, come more easily.
Business analysts possessing intellectual curiosity have voracious appetites for learning. They do not shy away from new or unfamiliar concepts but rather try to incorporate those concepts into their understanding. They tend to be very good listeners who absorb information like sponges.
Life coach, Dr. John D. Skare, Ed. D, defines intellectual curiosity as “a term used to describe one’s desire to invest time and energy into learning more about a person, place, thing or concept””
Are you really interested in the person or persons you are questioning and the information they possess or are you more interested in completing the requirements document? This intellectual curiosity is what drives us to ask more questions. Just as a child is curious about the whole world and his or her part in it, we can be curious about the whole business and our initiative’s part in it.
Developing intellectual curiosity is not difficult. We all are born with intellectual curiosity As children we truly want to know what the world is about, and what our place in the world is. We ask questions and more questions. Children, especially two-year olds, do not have to learn the “5 Whys”. They ask Why automatically without thinking. Over the years as we grow up we are taught not to ask questions. Research shows that young children have hundreds of questions every day, but by the eighth grade those same children ask only two questions a day on the average. Why?
“In school, we’re rewarded for having the answer, not for asking a good question.”
Richard Saul Wurman, original creator of the TED Conferences
Maybe it’s because the adults we are asking don’t know the answers and tell us to stop asking, or maybe we just get frustrated and stop asking. Perhaps it’s because we are conditioned by that age through school to have more answers and to ask less questions. 
As adults, especially in business, there is also another reason: we cannot afford to appear stupid by asking questions. People believe that they got their position or place at work because of what they know, their experience, and asking questions will belie that assumed knowledge. The belief is; if you are a “knowledge worker” and therefore paid for your knowledge, asking questions shows a lack of that knowledge and places your job, and perhaps career in jeopardy. And this includes business analysts. Despite the exhortation, “there are no stupid questions.”, Most people appear to believe more ardently that there are Stupid Questions, then that there are Right Questions.. After all, I don’t hear anyone asking how to ask stupid questions, and I doubt anyone that article titled “how to ask stupid questions.”
So what to do to recapture the attitude of intellectual curiosity? Think like a child? Well, yes. Listen naively as though you have never heard the information before, even if it is the eighth straight interview or information gathering session on the same subject. Assess the information you are receiving critically and think about what question you might ask. For example,
- Are there any words that might be ambiguous?
- Am I making any assumptions?
- Is the responder making assumptions?
- Can I get more details about what they are describing?
- Can what they are describing be construed generally?
- Is the information relevant to the question (if not why not? And how do I get relevant information)?
- Why is the responder answering the question in this particular way? (e.g. giving closed ended answers to open ended questions)
- What else don’t I understand about this answer or this situation?
- Why are they not able to answer a particular question? Who can answer it?
- Are they answering because they assume I expect an answer and not because they really know?
- Do they want to answer my questions now, or at all?
- And so forth
Is that all there is to asking the Right Questions?
To ask the Right Questions, you have to know what to ask, who has the information to answer the question, when the question is indeed answered, how to ask the question so that you get the information needed, how to analyze the information to produce the needed answer, where to place the answer among all the other information you have received, and when to go back to ask the question again.
Distilling it down: there are three basic skills to asking the Right Questions.
- Know what to ask the Right Question
- Know how to ask the Question the Right way
- Know how to analysis to determine the Right Answer
Since I’ve run about out of word space for this part of the article, I will end here. The next parts will address
- How to ask the Right Question by knowing what to ask
- How to ask the Right Question by knowing how to ask it
- How to avoid asking the wrong questions
Look for them in upcoming Business analyst Times issues.
Don’t forget to leave your comments below.
 ModernAnalyst.com, March 14, 2011
 Blais, Business Analysis: Best Practices for Success, John Wiley, 2011
 Coleman, Ken, One Question, Howard Books, 2013. Not only does this book describe the reason why we don’t ask questions and the importance of asking them (in the introduction) but it also contains examples of interview where Right Questions are asked. Remember however, the book and interviews are edited.