Questions? The typical three-year-old asks between 100 and 300 questions a day. Any parent of a toddler will tell you, it’s a constant barrage of questions. “Why this” and “why that”? They are typically open, innocent, blunt, curious, and never give up on their questions. Gradually, we see that most kids start questioning less and less. When they become teenagers, they may have learned to deflect others by saying “I don’t know” and “Everything is fine”. By adulthood, our ability to ask questions diminishes from the fear of looking silly or appearing stupid. We reach the point where we would rather make mistakes than ask questions. Without the courage to ask questions, we deny ourselves our best chance. Curiosity is not missing, it’s dormant. The challenge is to reclaim the curiosity of a three-year-old through the simple, powerful act of asking questions.

Questions Asked

The SurveyMonkey’s website claims there are 20 million questions answered on their platform every day. People ask about approximately 650 million question-based searches on Google every day. When I asked the same question to ChatGPT, it replied instantly: As of 2025, ChatGPT handles an enormous number of questions globally, about 2 to 2.5 billion prompts daily from users around the world. A significant share, ~40–45 % of ChatGPT prompts are traditional questions where users are seeking information. (E.g., “What is…?” “How do I?”). That is 900 million to 1.12 billion questions daily!

This takes me back to my own experience with questions and the emotions that came with it. Whenever I came home for the holidays, my father and I would slip easily into conversations I quietly cherished. He would ask me questions—gentle ones, never interrogating in the way parents sometimes do. Being a teacher, he seemed genuinely curious about my life: my routines, how I was doing, the friends I was spending time with. What stayed with me was how rarely he repeated himself; each visit brought questions that were easy, open, and full of attention. Now, years later, I hear myself asking my own children the question that has become my most familiar: “How was school?” At first, their answers arrived as complete sentences, sometimes even stories. But as the question settled into routine, those sentences slowly shrank into a single word – “Good.” Period. Nothing more was asked. It’s fascinating how questions often come with feelings attached.

Any questions?

In my consulting experience, I have frequently observed a noticeable decline in curiosity expressed through questioning within the workplace. Conversations tend to become one-way updates rather than genuine dialogue, and in large meetings, the routine prompt “Any questions?” is frequently met with silence—signaling disengagement rather than agreement. When questions are asked, they’re seen more as interruptions than helpful contributions, which naturally discourages further inquiry. I’ve had colleagues tell me privately that a question I asked helped them understand something they hadn’t before. Still, even with these clear benefits, asking questions remains surprisingly rare. This paradox inspired me to explore, in a friendly and curious way, how questions, meeting dynamics, trust, emotions, and interruptions affect workplace conversations—so everyone benefits.

Just Ask

So, how do we master the art of asking questions? In his book “Just Ask!”, Bill McGrane III defines a question as an inquiry or interrogation that shows you are interested in learning more about the other person or subject matter. I liked McGrane’s approach; he thinks deeply about something so routine – asking questions. Further, he writes that there are five foundational elements to the art of asking questions: 1) Ask questions with self-esteem; 2) Be aware of impact words; 3) Listen externally; 4) Discover the best outcome for the person in conversation; and 5) Develop sensing skills. Bill McGrane, highly respected as one of the world’s foremost speakers on personal and professional advancement, says that asking questions is 90% planning and preparation, 10% execution.

I never realized there could be a design step in preparing a question – what a revelation! What you do internally before asking shapes the outcomes you will get from others. By laying the groundwork, truly focusing on the other person, and listening deeply, you gain insight into what matters most to them. With this understanding, you can craft a thoughtful, “designed” question that speaks their language and resonates meaningfully. Talking about self-esteem, Bill McGrane writes,

“ Until you have self-esteem, you won’t be comfortable putting yourself in uncomfortable situations. ”

He is so right on this. “Just Ask!” goes further by stating that there are five types of questions: 1) Safe question; 2) Closed question; 3) Open question; 4) Interview question; and 5) Congruent question.

Safe questions naturally draw out information, require no deep analysis, and, most importantly, build trust—creating the space for meaningful conversation. (E.g., How is your family doing? Read any interesting books recently? How are you doing?) Closed questions elicit brief answers like “yes/no” or multiple-choice, speeding communication, but they rarely spark deeper conversation. (E.g., Is this something that you want to do now? Could I have a moment to get your opinion on last week’s report? Don’t you agree?) Open-ended questions are like essay test questions. They call for the individual to elaborate. (E.g., Tell me about yourself? How do you like to spend time when you are not working?) Interview questions focus deeply, guide the conversation, and signal genuine interest in learning more. (E.g., What are you going to do if you can’t change the situation? What do you think about it? How do you feel about this?) Congruent questions are focused, sensitive, and often reveal feelings; asking them effectively requires self-awareness, harmony with the other person, full attention, and strong social skills, though without this alignment, they can backfire. (E.g., If you don’t do this, what will you do? What is it costing you by not taking action? When was the last time you read a book?)

One of my beloved Theoretical Physicists, Richard Feynman, says, the more you ask questions, the deeper your understanding of your subject grows, and the more interesting it gets. Feynman was influenced by his father, who encouraged him to ask questions to challenge orthodox thinking. Asking questions is an effective way to improve beliefs.

“ Socrates is believed to have said: “All knowledge starts with doubt. ”

The Socratic Way

Talking about the art of asking questions without mentioning Socrates would be incomplete—his method of asking questions, popular in ancient Athens, inspired the modern Socratic approach used in American schools around the 19th century, where students respond openly to thoughtfully posed questions. A guide to the 1904 New York State Uniform Examination provided a typical “correct” definition of the Socratic method: teaching “by means of questions”. The Socratic method is widely believed to enhance student engagement and promote critical thinking.

What value does any art or philosophy hold if it is not actively applied in the way we work? I aim to embed the art of asking questions into the foundation of Data and AI Governance, enhancing our ability to ask the right questions and drive optimal outcomes in managing information assets. Our ability to shape our questions to fit the moment and its needs. I remember one moment: I asked a simple question to a data architect—“Why build such a huge dictionary?”—and his sharp stare reminded me just how easily genuine curiosity can be misread. Listen intently, and it opens the door for people to discover an appropriate resolution through answering the questions you ask. If we are dead set in on obtaining our own personal outcome, we may not hear what the person is saying, which will cause a disconnect. That is the reason I opted for “Lead by Listening”, a prerequisite for this principle of conduct.