The Subtle and Critical Art of Questioning


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Lawyers have known all along that the way word their question to a witness, determines the response they get from the witness. They have used this practical knowledge for decades to both right the wrongs and wrong some rights. 

In a research paper titled, “Eliciting the Truth, the Whole Truth, and Nothing But the Truth: The Effect of Question Phrasing on Deception,” Maurice Schweitzer (Wharton professor) & his team of researchers discovered that subtle tweaks in the way a question is asked can lead to profoundly different answers. 

We know that the ability to ask good questions can go a long way in how effective we are as leaders, entrepreneurs or in the process of discovery and innovation. Questions typically create the frame of reference within which the answer is thought in. They create the prototypical “Box” and if we are to think outside the box, we need to create a different question that allows us to think in a bigger box. We can never truly think outside the box but we can definitely think in a different box. 

There are many ways to learn the skill of asking the right question. No better way than to practice and learn by doing. 

I try to practice this in every interaction that I have. I practice it by hosting thought leaders on a podcast and ask them questions. In all the years of hosting the podcast and questioning people, I have learnt something that I have found to be most profound and useful. 

Purpose of the question: 

It is important to understand what it is that we are trying to achieve by asking these questions and whom are we asking them off.

If our purpose to learn or prove facts (what happened, when, to/with whom, etc) then the kind of questions are very different.

If our purpose is to learn something new from the person whom are asking the question (asking an expert/teacher to explain something to us), then the kind of questions that we ask is very different. 

If our purpose is to go on a journey with the person answering the question, to explore something that (s)he is still not sure of, then the kind of questions we ask is very different. 

If we are trying to understand the root cause of an issue that we are trying to solve, then the kind of questions that we need to ask is very different. 

Positive, Negative or Neutral: 

Irrespective of the purpose, every question can be framed in a positive, negative or a neutral tone. The research that Maurice and team have done shows that the tone of the question has a significant impact on the kind of answers that we get. 

For example, Marshall Goldsmith, in his book “Triggers” talks about employee surveys and how the wording in the survey questions usually exonerates the role that an employee can play in their engagement levels within the business. Just by rewording the questions (Instead of “What did the company do to help you” asking “What did you do to help yourself or the company”) on the survey, not only can the responses change significantly but also the attitudes of the employees but also change the expectation that it is not just the job of the business to work on increasing employee engagement but it is both the role of the business and the employee to work on it together as a team.

Effectiveness of Good Questions 

Irrespective of the type of questions that we ask or frames of reference that we enforce for our thinking, one thing is very clear. We need to be intentional about the tone and purpose of the questioning.  In some cases, it might even be helpful to explore different ways of asking the same questions to look at the topic from different perspectives and frames. 

We also need to be open to listen and understand the answers and the influence that the way we framed our question impacted the answer. I believe the ability to introduce awkward silences in the conversation after asking the questions and staying in the moment with the person answering the question can go a long way in getting them to open up and share things that they might not even be aware of themselves. 

In Conclusion:

We today live in a world where we are losing the ability to question everything happening around us from multiple perspective. In most cases, we have even stopped questioning and holding people responsible for their actions. This is a dangerous trend, one that will lead us to further alienate ourselves from others who are different and think differently. 

PS: I try to delve into these things in my latest book that you can buy here – Thrive: Mindsets & Skillsets needed to succeed in a world dominated by smart machines & intelligent algorithms

PS: Here is an HBR post that you will like on the art of questioning. 

Republished with author's permission from original post.

Mukesh Gupta
I currently work for SAP as Customer advocate. In this capacity, I am responsible to ensure that the voice of the customer is being heard and play the bridge between customers and SAP. Prior to joining SAP, I have worked with different organizations serving in different functions like customer service, logistics, production planning & sales, marketing and business development functions. I was also the founder-CEO of a start-up called "Innovative Enterprises". The venture was in the retail & distribution business. I blog at


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