The art of questioning | The Manila Times

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“Asking the right questions is half the answer.” – Unknown

THE art of questioning is an essential skill that transcends professions, industries and fields of expertise. It is the foundation of critical thinking, problem-solving and decision-making. However, mastering the art of asking the right questions requires a deep understanding of context, an awareness of the nuances of human communication and a commitment to seeking clarity rather than confusion.

The importance of this skill can be clearly illustrated in various situations, including in business settings where success of a negotiation, a deal, or even an entire project may hinge on the quality of the questions asked. Unfortunately, even in high-stakes environments like legislative inquiries, there are instances where poor questioning can lead to confusion, deflection or a complete derailment of the intended purpose.

A striking example of ineffective questioning can be seen particularly during Congressional inquiries involving Philippine Offshore Gaming Operators (POGOs).

During the hearings, some lawmakers, instead of asking targeted, incisive questions, sometimes pose vague, leading or irrelevant questions to the resource persons, only leading to confusion or evasive answers. In these instances, the hearing often loses its focus, reducing what should be a rigorous investigation into a platform for grandstanding. It is in these moments where the art of questioning is lost, and the hearing’s goal of uncovering the truth becomes secondary to the theatrics of the Congressional inquiry process.

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Questioning for growth, problem-solving

In contrast, effective questioning can lead to profound insights and solutions, particularly in business. Business leaders, managers and entrepreneurs who understand the art of questioning know how to use this skill to drive growth, foster innovation and solve complex problems. In a business context, the ability to ask good questions is not just about gathering information — it’s about gaining clarity, challenging assumptions and facilitating productive conversations.

One of the key principles in the art of questioning is the ability to ask open-ended questions that encourage thoughtful responses. In contrast to closed questions that can be answered with a simple “yes” or “no,” open-ended questions require the respondent to think more deeply and provide more detailed answers. For instance, in a business negotiation, rather than asking, “Do you agree with this proposal?” a more effective query would be, “What are your thoughts on this proposal and how do you think it can be improved?” This type of question enhances communication, fosters collaboration and can result in more creative and advantageous solutions for both parties.

In the corporate world, the famous “Five whys” technique is another example of how questioning can be used to identify the root cause of a problem. This method, which involves asking “why” five times in succession, is often used in business to get to the bottom of an issue. For instance, if a company experiences a decline in sales, a manager might start by asking, “Why are our sales declining?” The answer could be, “Because our customer base is shrinking.” The next “why” might be, “Why is our customer base shrinking?” The process keeps on until the root cause of the issue is revealed, which could be anything from poor customer service to changes in the market. This technique exemplifies how asking the right questions can lead to valuable insights and more effective problem-solving.

The importance of asking the right questions is also evident in the field of management consulting. Consultants are often brought into a business to help solve complex problems, and their success largely depends on their ability to ask the right questions. They need to gather information quickly, understand the client’s challenges and identify opportunities for improvement. One of the first things a consultant might ask a client is, “What do you hope to achieve with this project?” This question helps to clarify the client’s goals and sets the stage for further inquiry into how those goals can be accomplished.

Framed with clarity and purpose

However, in order for questions to be effective, they must be framed with clarity and purpose. Just as in the Congressional hearings on the POGO issue, where poorly framed questions led to unsatisfactory responses, in business, a poorly worded or ambiguous question can lead to confusion and miscommunication. For example, a manager asking, “Why are we not doing better?” might not get as useful a reply as asking, “What specific challenges and issues are we facing that are preventing us from meeting our targets and objectives?” The latter query is more likely to get a useful and thorough answer.

Another important aspect of the art of questioning is listening. In both business and legislative inquiries, the question is only part of the equation; the way in which the answer is received is equally important. Too often, in hearings and meetings alike, the person asking the question is already thinking of the next question rather than listening to the answer. This can lead to missed opportunities for deeper understanding or further probing. Good questioning, therefore, requires active listening, which allows the questioner to build on the respondent’s answers and steer the conversation toward a productive direction.

The art of questioning is a vital skill that, when wielded effectively, can unlock new insights, drive innovation and solve complex problems. By honing this skill, professionals across industries can foster more meaningful conversations, uncover deeper insights and ultimately achieve better outcomes.


The author is the founder and CEO of Hungry Workhorse, a digital, culture and customer experience transformation consulting firm. He is a fellow at the US-based Institute for Digital Transformation. He teaches strategic management and digital transformation in the MBA Program at De La Salle University. The author may be emailed at [email protected].

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