The Art of Questioning

George Morris
5 min readOct 11, 2023

Asking questions is a skill we often overlook despite its crucial role in shaping our lives, careers, and relationships. You’ve probably been in a conversation where you’re just waiting for your turn to speak, haven’t you? You nod your head, pretending to listen, but your mind is racing, crafting that perfect response or that smart-sounding comment. I get it; we’ve all been there.

But in doing so, what valuable insights might you be missing? What deeper connections are you sacrificing?

Questions build trust and strengthen bonds. Social psychologist Arthur Aron made headlines for creating 36 questions that can make two strangers fall in love. The mutual vulnerability created by sharing personal answers to Aron’s unusual questions build intimacy between participants.

As Voltaire once said, “Judge a man by his questions rather than his answers.” The questions we ask reveal a lot about how we think, what we value, and the depth of our curiosity. Learning to ask better questions can transform our relationships, careers, and view of the world.

The Downside of Not Asking Questions

Before get into the “how-to’s,” let’s consider the consequences of not asking questions. Envision a corporate meeting where team members are more interested in stating their points than exploring new ideas. The outcome? Stagnant creativity.

Or think about a relationship where partners don’t ask about each other’s day, feelings, or thoughts. The result? Emotional distance. A lack of meaningful questions doesn’t just stunt conversation; it stunts growth — personal, professional, and emotional.

Questions are powerful because they direct our attention. As author Warren Berger puts it, “The questions we ask determine what we find.” Questions help us challenge assumptions, spark creativity, and get to the heart of complex problems.

Why We Don’t Ask Great Questions

It’s not like we’re intentionally avoiding asking questions. From a young age, we’re taught to provide answers, not to probe. School is a classic example: you get gold stars for reciting facts, not for asking why the sky is blue or how feelings work. And let’s not forget the cultural factors. Some societies value forthrightness and assertiveness over curiosity. All these elements contribute to a conversational environment that’s more about monologues than dialogues.

If questions are so important, why do we settle for mediocre ones? Here are some common obstacles to consider:

Assumptions — We often ask narrow questions that confirm what we already believe. Curiosity requires challenging assumptions and acknowledging that the full truth is complex.

Impatience — In conversation, we often rush to share our perspective rather than listening patiently. Good questions emerge from focused listening.

Fear — Asking probing questions can feel risky, as they reveal gaps in our knowledge. But being vulnerable is required for learning and connection.

Low self-awareness — We may not realize that our current questions lead to suboptimal outcomes. Reflecting on the quality of our questions takes humility. This can be build by working on our Emotional Intelligence (EQ).

The Art of Listening

Before you can ask a great question, you need to listen — truly listen. But let’s be clear: listening is far more intricate than it sounds. It’s not just about letting the other person’s words wash over you while you nod along. It’s an active, not a passive, endeavor. Your ears catch the words, sure, but your mind should be piecing together the underlying messages, the subtext that often speaks louder than any spoken sentence. Are they frustrated? Hopeful? Confused? The tone of their voice, the pace of their speech, and even the hesitations between words give you clues. And when you pick up on these, you’re not just hearing; you’re listening.

When you master the art of listening, you open a new level of dialogue. You’re not just trading facts or opinions; you’re trading emotions, values, and insights. You’re piecing together a puzzle that is the other person’s worldview. A simple nod transitions into a deep understanding, making the other person feel seen and valued. And let’s be honest, who doesn’t want to be the person everyone feels understood by?

This understanding sets the stage for asking questions that are not only thoughtful but also deeply empathetic. Once you find the courage to ask the deep questions you’ll remove walls and open new doors to new ideas and perspectives.

Tips for Becoming a Better Listener

  1. The Power of Silence — Often, the most critical information is shared when you give the other person room to think and speak. Resist the urge to jump in immediately with your own thoughts or questions. A moment of silence can often encourage deeper reflection and more meaningful responses.
  2. Non-Verbal Cues Matter — Don’t underestimate the importance of eye contact, nodding, and other non-verbal signals. These cues can convey attentiveness and empathy, encouraging the other person to open up more.
  3. Reflect and Validate — When the other person is done speaking, briefly summarize what you’ve heard or ask a clarifying question. This not only shows that you’ve been paying attention but also gives them a chance to correct any misunderstandings before the conversation moves on.

Tips for Asking Better Questions

Alright, so you’re all ears now. What’s next? Here are some tips to elevate your question-asking game:

  1. Go Beyond the Surface — Instead of asking, “How was your day?” try, “What was the most challenging part of your day?”
  2. Be Specific — Vague questions get you vague answers. If you’re discussing a project, ask targeted questions like, “How do you think we could improve the user interface?”
  3. Open-Ended Magic — Use open-ended questions to invite discussion. “What are your thoughts on this?” opens up a space for diverse opinions.
  4. Get Reflective — Take note when conversations feel dull or ineffective. Reflect on how asking different questions could enliven the dialogue.
  5. Follow-up — One good question deserves another. If someone offers an intriguing point, dig deeper. Ask, “Could you elaborate on that?”
  6. It’s About THEM — Identify situations where you tend to give advice. Could you instead ask insightful questions to let others uncover their own solutions?
  7. Be Vulnerable — Sometimes, asking a sensitive question can break down barriers. If the atmosphere is right, don’t shy away from questions like, “How did that experience shape your perspective?”

Don’t underestimate the power of a well-placed question. Questions spark curiosity, and curiosity is the gateway to empathy, innovation, and deeper understanding. So the next time you find yourself drifting off in a conversation, waiting for your moment to shine, stop.


And then, ask a question that matters. Because the questions you ask don’t just shape the conversation; they shape your world.

Question-asking is a skill we can continually refine. With practice and commitment, we can refine the art of asking great questions.



George Morris

Lifelong entrepreneur and business coach, single father of two. Looking for ways society can level-up to meet the modern global challenges.