How to ask better questions for great conversations

How to ask better questions for great conversations

How to ask better questions for great conversations

The last new years, instead of making resolutions, I have been writing an intention for each of the different areas of my life. It is not a goal, it serves more as a note to me about how I want to grow in my work, family, health, etc. This year, next to the “relationship” category, I wrote the words, “Ask better questions and practice a deeper listening.” Because figuring out how to ask better questions isn’t intuitive for everyone!

I knew that really showing myself to the people I love meant that our conversations should be a place where they felt valued and heard.

My struggle wasn’t about not being interested in what they had to say, it really was. But sometimes my monkey mind would race so fast from one thought to another that I was distracted and just to lose a fundamental part of what they said. Or even if I heard him on the surface, I wasn’t listening deeply enough to understand the deeper meaning behind his words.

As I wrote earlier about getting more curious, I was reminded of my favorite class in high school. It was AP Literature with Mr. Stover, who was reputed to be one of the toughest teachers in the school. I loved that class, mainly because we learned to use the Socratic method to decode poems and novels that, at first, seemed impossible to me. (Waste land by TS Eliot, anyone?) We would circle around our desks and spend the entire hour asking and answering questions that would help us think more critically and come up with new ideas.

The power of questions stuck with me, but figuring out which ones will work best for a conversation requires a high level of emotional intelligence and a lot of practice. So let’s get into it.

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First, really listen.

We’ve all been in that situation when we tell a story, and the other person asks a semi-random question that reveals that they were only half listening. Or, we ourselves have been the perpetrators because our minds drifted during the conversation. Either way, it doesn’t feel right.

By training ourselves to tune in and really listen while the other person is speaking, it sets the stage for naturally asking good questions that come from a genuine place of curiosity.

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How to ask better questions for great conversations

Ask more questions.

According to Harvard Business Review, most of us don’t ask enough questions. They cite research showing that “among the most common complaints people make after having a conversation, such as an interview, a first date or a work meeting, are ‘I wish I had asked more questions’ and’ I can’t believe that she didn’t ask me any questions. ‘

Not only does the mere act of asking questions pave the way for learning all kinds of unexpected things about the other person; There is no safer way to increase your level of sympathy than by being an interested person. The lesson? Even if the exact way you ask your questions needs improvement, you are already one step ahead just by asking more questions.

I love this example of the comments: “Tell me how you came to live in Austin. What are your favorite things to do here? “

Other big questions include:

  • Is there a new hobby or habit that you started during the pandemic and that you plan to continue?
  • What was the best vacation you took and why?
  • If you had the opportunity to start your entire career from scratch, what would you do instead?
  • What are your top three karaoke songs and why?
  • What was the first celebrity you fell in love with? Do you think they influenced the type of person that still attracts you?
  • What was the first book you remember that you really loved? Is it still one of your favorites?

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How to ask better questions for great conversations

Ask follow-up questions.

This practice has been a game changer for my relationship with Henry (by the way, young children have excellent radar for knowing if you are really listening to them). By asking, “What makes you say that?” or “How did that make you feel?” you can feel my genuine commitment, and that actually careful about what you are sharing.

In other words, it validates the other person who is being heard, which on a deeper level shows how much you value them. In Henry’s case, when I set out to ask him these kinds of questions, he’s less likely to break down or feel frustrated because I have a deeper understanding of his perspective and can respond accordingly.

The next time you talk to someone and say something that is a bit vague, instead of just accepting it and moving on, try asking, “What exactly do you mean by that?” I guarantee that just by doing this, your conversations will improve instantly.

Consider these complements to common questions to start a more meaningful conversation:

  • How was your day? What was the best part?
  • How is your mom? How are your days lately?
  • Can you help me understand that a little better?
  • What motivates you to do / say that?
  • How does that play out in your daily life?
  • Do you think you would ever change your mind about this in the future?

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How to ask better questions for great conversations

Ask open questions.

This is one that I have really seen in action when interviewing our Tastemakers and Wake Up Call talents over the years. When I ask closed questions that can be answered with a “Yes” or a “No”, the answers not only induce yawning, but I also walk away feeling that I did not learn anything substantial about the other person.

But when I choose a open question that requires them to develop, the answers often surprise me and leave me (happily) wanting more (see “follow-up questions” above). An open-ended question does not make assumptions, reveal biases, or put the other person in a box. Communicate that we will make time for their complete response and invite the other person to share it completely without rushing.


  • What has happened the most to you since we last spoke?
  • What do you think about …?
  • What was your favorite chance encounter?
  • How did you feel about your last big meal out? What makes it so special?

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How to ask better questions for great conversations

Suppress the urge to interrupt.

Well, this one is especially aimed at me. I’ll be honest, I don’t want interrupting, I really don’t, but I often get so excited or want to share how much I “understand” what the other person is saying that I chime in just before they finish speaking.

The end result (in addition to being annoying) is that they feel rushed or that the conversation is headed in a different direction than they were heading. Show some respect (Camille!) I’m working to get comfortable with a moment of silence and letting my ego take a backseat in conversations so I can “I seek to understand more than I seek to be understood. “


For more proof of how powerful asking good questions can be, read this article “Modern Love” which states: mutual vulnerability fosters closeness. To quote the study authors, “A key pattern associated with developing a close peer relationship is sustained, growing, reciprocal personal self-disclosure.” The 36 questions they used in the experiment are some really good ideas that I’m planning to try in future conversations.

What’s your favorite question to ask someone you’re trying to get to know better?

This post was originally published on July 25, 2019 and has since been updated.