How to Ask Better Questions for Great Conversations

Asking better questions, and practicing deeper listening is one resolution I hope to achieve this year.

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.

There is no such thing as a stupid question but there are definitely questions that’s definitely better to ask than others. Questions are super powerful, 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.

Most of us don’t ask enough questions. 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.

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?

Ask follow-up questions.

This practice is game-changing.

By simply asking, “What makes you say that?” or “How did that make you feel?” you can sense genuine engagement, and that someone actually cares about what is being shared. 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.

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?

Ask open-ended questions.

Close-ended questions that can be answered with a “Yes” or “No,” not only are the answers yawn-inducing, one can also walk away feeling like they didn’t learn anything of substance about the other person.

But when you choose an open-ended question that requires them to elaborate, the answers will often surprise you and leave you (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. I gotten show some patience and respect haha! I always feel like silence is awkward but I’m slowly learning that silence can be a good thing and working on being comfortable with a bit of peace, and letting my ego take a backseat in conversations so that I seek to understand more than I seek to be understood.


Conversations are fun, entertaining, and engaging but it takes practice to maintain one. Holding a conservation is super beneficial, it’s the key to language development, the exchange of thoughts and ideas and listening to each other. People learn by hearing each other’s thoughts while observing facial and body expressions that show emotions.

Conservations also lead to honest and long-lasting friendships and having friends for life is always the best feeling in the world.

Let us know in the comments below what’s your favorite question or conversation-starter.

Stay healthy and live life to the fullest.

Xoxo, Messycafe.


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