How to Ask Better Questions for Great Conversations

How to Ask Better Questions for Great Conversations

In the past few years, instead of making resolutions, I have written down an intention for every different field of my life. This is not exactly a goal. It is more like a hint to myself, telling me how to grow up in work, family, health, and so on. Recently I wrote “ask good questions and practice deeper listening, under the “relationship” category.” Because not everyone can intuitively figure out how to ask better or appropriate questions for Great conversations!

I know that really showing up for the people I really love means that our conversation must be a place where they feel valued and listened to.

My struggle is not that I’m not interested in what they say – I’m really interested. But sometimes my monkey mind moves from one thought to the next so fast so that I get distracted and just miss the key part they say. Or, even if I heard it on the surface, I didn’t understand the deep meaning behind their words because I was not listening deeply enough.

As I wrote earlier about becoming more curious, I recall my favorite class in high school. Mr. Stover, considered one of the toughest teachers in the school, is AP literature. I like that course mainly because we have learned how to interpret poetry and novels in a Socratic way. At first, these poems and novels made me feel impossible to read (The Waste Land-written by T. S Eliot, anyone?) We had to circle up our tables and were spending time asking and answering questions that will help us think more critically and lead to new ideas.

The power of questions has always haunted me, but knowing which question is best for conversation requires a high level of EQ and a lot of practice. Let’s start.

How to Ask Better Questions for Great Conversations –

First, listen carefully.

We all have been experienced, when we tell stories, sometimes another person asks a semi-random question, which shows that they only listen to half of the stories. If not, we have been the perpetrators because our minds deviated or drifted away in the middle of the conversation. Anyway, it doesn’t feel good.

By training yourself to really listen when others are talking, it lays the foundation for naturally asking good questions from real curiosity.

Ask more questions.

According to the Harvard Business Review, most of us don’t ask enough questions. The research they cited shows that “the most common complaints after a conversation, such as an interview, a first date or a work meeting, are ‘I hope she asked me more questions and I can’t believe she didn’t ask me any questions .”

The pure act of asking questions not only paves the way for understanding each other’s unexpected things; There is no more reliable way to improve rapport than to be interested in others. Lesson? Even if the exact way you ask questions needs to be improved, you’re one step ahead by asking more questions.

I like the example in this comment: “tell me how you came to live in Austin. What do you like best to do here? “

Other major questions include:

  • During the influenza pandemic, do you have a new hobby or habit that you plan to keep up with?
  • What was your best vacation? Why?
  • If you had the chance to start your whole career from scratch, what would you do?
  • What are your three favorite karaoke songs? Why?
  • Who was your first crush on celebrities? Do you think they affect the people you are still attracted to?
  • What is your favorite first book? Do you still consider it as one of your favorites?

How to Ask Better Questions for Great Conversations-

Ask follow-up questions.

This practice changed my relationship with Henry. (by the way, if you’re really listening to the children, they’ll have a good radar.) By asking, “why do you say that?” Or “what do you think?” He can feel my real involvement, and that makes me actually care about what he’s sharing.

In other words, it confirms to another person that they are being listened to, which shows how much you value them at a deeper level. Take Henry as an example. When I specifically ask him such questions, he is unlikely to collapse or be depressed because I have a deeper understanding of his views and can respond accordingly.

The next time you talk to someone, they say something vague, instead of just accepting it, and then go on, try to ask, “what do you mean by that?” I promise that doing just one thing will make your conversation better immediately.

Consider these additional questions to trigger a more meaningful dialogue:

  • How are you today? What’s the best part?
  • How’s your mother? How’s she doing?
  • Can you help me understand this better?
  • What prompted you to do / say so?
  • What happens in your daily life?
  • Do you think you will change your mind about this down the line?

Ask open-ended questions.

This is what I really saw when I interviewed our Tastemakers and woke up call talent over the years. When I ask some closed-ended questions that can be answered with “yes” or “no”, the answer will not only make people yawn but also when I walk away, I feel that I have not learned anything substantive from each other.

However, when I choose an open-ended question that they need to elaborate on, the answer often surprises me and makes me (happily) want more (see “follow-up questions” above). Open-ended questions do not make assumptions, expose prejudices, or put others in a box. It conveys that we will make time for their complete answers and invite others to share them fully in a leisurely way.

Give it a try:

  • what’s your favorite thing that happened since we last talked?
  • What do you think of?
  • What was your favorite chance encounter?
  • How did you feel about the last good meal you had outside? What makes it so special?

How to Ask Better Questions for Great Conversations-Resist the urge to interrupt others.

This one is for me. To be honest, I don’t want to interrupt others. I really don’t want to, but I’m often excited or want to share my “understanding” of what others say. I cut in before they finish.

The end result (except annoying) is that they feel in a hurry, or the direction of the conversation is different from their destination. Show some respect, I’m trying to calm myself down and make myself subordinate in the dialogue so that I “seek to understand more than to be understood.”


If you want more evidence of how powerful it is to ask good questions, please read this “modern love” article, which asserts that mutual vulnerability promotes intimacy. “A key pattern associated with developing intimacy among peers is continuous, escalating, mutual and personal self-disclosure,” the study’s authors are quoted as saying The 36 questions they used in the experiment are some very good starting points for thinking, which I plan to explore in future dialogues.

What is your favorite question to ask someone you want to know more about?

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