How to Ask Better Questions for Great Conversations

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The last several New Years, instead of making resolutions, I’ve been writing out one intention for each of the different areas of my life. Not quite a goal, it serves more as a note to myself on how I want to grow in my work, family, health, etc. This year next to the “relationship” category, I wrote out the words, “Ask better questions, and practice deeper listening.” Because figuring out how to ask better questions is not intuitive for all!

I knew that really showing up for the people I love meant that our conversations must be a place where they felt valued and heard.

My struggle wasn’t about not being interested in what they had to say—I genuinely was. But sometimes my monkey mind was racing so fast from one thought to the next that I would get distracted and just miss a critical part of what they were saying. Or even if I heard it on the surface, I wasn’t listening deeply enough to understand the deeper meaning behind their words.

As I wrote earlier about becoming more curious, I thought back to my favorite class in high school. It was AP Literature with Mr. Stover—who was reputed to be one of the toughest teachers in school. I loved that class, mainly because we learned how to use the Socratic method to decode poems and novels that, at first read, felt impossible to me. (The Waste Land by T. S. Eliot, anyone?) We’d circle up our desks and spend the entire hour asking and answering questions that would help us think more critically and draw out new ideas.

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

First, actually listen.

We’ve all been in that situation when we’re telling a story, and the other person asks a semi-random question that reveals they were only half-listening. Or, we’ve been the perpetrator ourselves because our minds drifted off while in conversation. Either way, it doesn’t feel good.

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

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, is ‘I wish she had asked me more questions,’ and ‘I can’t believe she didn’t ask me any questions.’”

Not only does the sheer act of asking questions pave the way for learning all kinds of unexpected things about the other person; there’s no more surefire way to amp up the level of rapport than being a person who’s interested in others. The lesson? Even if the exact way you pose your questions needs work, you’ll already be one step ahead just by asking more of them.

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

Other great questions include:

  • Is there a new hobby or habit that you started during the pandemic that you plan to keep up with?
  • What was the best vacation you ever took and why?
  • If you had a chance to start your entire career over from scratch, what would you do instead?
  • What are your top three karaoke songs and why?
  • Who was your first celebrity crush? Do you think they influenced the kind of person you’re still attracted to?
  • What was the first book you remember really loving? Is it still one of your favorites?

italy dinner party, conversation

Ask follow-up questions.

This practice has been game-changing for my relationship with Henry (btw young children have an excellent radar for if you’re really listening to them.) By asking, “What makes you say that?” or “How did that make you feel?” he can sense my genuine engagement, and that I actually care about what he’s sharing.

In other words, it validates to the other person that they’re being heard, which on a deeper level shows how much you value them. In Henry’s case, when I make a point to ask him these types of questions, he’s less likely to meltdown or be frustrated because I have a deeper understanding of his perspective and can respond accordingly.

Next time you’re talking with someone and they state something that’s a little vague, instead of just accepting it and moving on, try asking, “What exactly do you mean by that?” I guarantee that just doing this ONE thing will make your conversations instantly better.

Consider these add ons to common questions to spark a more meaningful conversation:

  • How was your day? What was the best part?
  • How is your mom? What are her days looking like lately?
  • Can you help me understand that a bit better?
  • What motivated 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 down the line?

friends, fire pit, hanging out

Ask open-ended questions.

This is one that I’ve really seen in action when interviewing our Tastemakers and Wake Up Call talent through the years. When I ask close-ended questions that can be answered with a “Yes” or “No,” not only are the answers yawn-inducing, I also walk away feeling like I didn’t learn anything of substance about the other person.

But when I choose an open-ended question that requires them to elaborate, the answers often surprise me and leave me (happily) wanting more (see “follow up questions” above.) An open-ended question doesn’t make assumptions, reveal biases, or put the other person in a box. It communicates that we’re going to make time for their full answer, and invites the other person to fully share in an unhurried way.

Try:

  • What’s your favorite thing that’s happened since the last time we spoke?
  • What are your thoughts on…?
  • What was your favorite chance encounter?
  • How did you feel about your last great meal out? What made it so special?

Restrain the urge to interrupt.

Okay, this one is especially directed at me. I’ll be honest—I don’t want to interrupt, I really don’t, but I often get so excited or want to share how much I “get” what the other person is saying that I jump in just before they’re done talking.

The end result (aside from being annoying) is that they feel rushed or that the conversation is taken in a direction other than where they were headed. Show some respect (Camille!) I’m working on being comfortable with a moment of silence, and letting my ego take a backseat in conversations so that I “seek to understand more than I seek to be understood.”

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If you want more proof of how powerful asking good questions can be, read this “Modern Love” article that asserts: mutual vulnerability fosters closeness. To quote the study’s authors, “One key pattern associated with the development of a close relationship among peers is sustained, escalating, reciprocal, personal self-disclosure.” The 36 questions they used in the experiment are some really good thought starters I’m planning to take for a spin 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.

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