If someone asks these 12 questions, they’re a great conversationalist

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Sometimes conversation just flows with ease, whilst other times it’s filled with awkward silences and forced polite chit-chat.

It makes a big difference who we’re talking to and whether we feel a connection. Because, of course, it’s much easier to find things in common with the people who we just click with.

But great conversationalists have the ability to cross barriers. They seem to effortlessly mix with all types of people from all sorts of backgrounds.

They are able to show empathy and understanding. They take an interest in others and display real curiosity. And they open up to show vulnerability.

That’s why, if someone asks the following questions, you can tell that they’re a great conversationalist…

1) “That’s so interesting. Can you tell me more?”

It’s not just about the initial question. It’s all in the follow-up.

Encouraging someone to continue shows your appreciation for and interest in what they have been telling you.

It’s a way of giving them permission to go on talking. And the truth is that we all like to talk about ourselves.

Someone who is enthusiastic about what we’re saying makes us feel special.

Research has shown that asking questions makes us more likable. But in particular, follow-up questions.

2) “So anyway enough about me, what have you been working on lately?”

It’s less the question you ask that is important here, and more about the technique you’re using.

Let me explain:

When a great conversationalist has finished explaining something about themself, they turn the discussion back onto the other person.

They recognize there are two people who need to have the room to talk.

A good chat flows from one person to the other, that means no hogging the limelight and actively trying to share it.

3) “That’s something I know absolutely nothing about, will you explain it to me?”

Rather than feel embarrassed or try to change the subject when they encounter unfamiliar territory a brilliant conversationist will use this to their advantage. 

It’s a win-win.

Not only do they get to learn something new, but they give the other person a platform to share their expertise.

Whenever you dig deeper, it displays your curiosity and that is always an attractive trait in someone.

4) “Hmm, and how do you feel about that?”

A skilled conversationalist never assumes. They always ask.

So rather than jump in with an opinion, like:

“Wow your boss sounds like a jack-ass” or “Ouch, you must have been totally gutted”

…they’ll give you the space to explain your emotions for yourself.

They won’t put words in your mouth. They’ll let whatever happened be about you, not them.

And they’ll gently and sympathetically tease things out by offering you the opportunity to share your feelings on the matter.

5) “I’m sorry that happened, do you want to talk about it?”

It can be a tricky balancing act. Showing concern without coming across as prying.

That’s why someone who understands this will always offer an ear, but never push.

It’s ultimately about recognizing other people’s boundaries and showing respect for them.

They won’t dive in with “What happened exactly?”

They won’t start digging for details that you would rather not share.

They will let you know that they’re available to talk but that you don’t have to.

6) “I’m curious, what do you make of it all?”

It might be a current affairs story or something that has happened.

But rather than dive in and lecture you on their thoughts, they want to know yours.

We all want to feel seen and heard. It’s this that makes us feel validated.

By asking someone their opinion on a matter you show them that their thoughts and feelings count.

7) What do you think you would do in that situation?”

Again, this is another question that invites someone to share their insights.

You don’t necessarily need to be looking for advice. You can also just be showing a general interest in how someone else would approach a scenario.

It gives you a deeper look into how someone thinks and helps you get to know them better.

And much like our previous question, it also gives them that feeling that what they have to say is important to you.

8) “I don’t think I agree with you, but I’d really like to try to see your side, so can you share more?”

The exact wording of this matters less than the overall message.

The key points are:

  • You don’t see eye to eye (and you stay true to yourself by sharing that)
  • You are not instantly dismissing their point of view
  • You stay open and show curiosity in learning more

Whenever someone feels judged or dismissed, they’re simply going to shut down.

Not only is that bound to cause some hostility, but you may be missing an opportunity.

Who knows, you may well learn something from what they have to say.

Either way, we show respect to others when we allow them to voice their opinions — whether we agree with them or not.

9) “That must have been hard?”

Questions like this show empathy and compassion.

And if there is one thing that gives a conversationalist their superpower — it’s having these types of sympathetic traits.

Because it’s this that allows them to reach out and walk in someone else’s shoes. And that creates bonds that tie us all.

Regardless of our differences, we all experience a wide range of emotions.

So we can always tap into those feelings, even when we don’t have personal experience of the situation that caused them.

10) I heard something I think is pretty funny/strange/interesting the other day. Did you know that…?

Yes, a big part of being an awesome conversationalist is encouraging others to speak.

But that’s not all it is.

A conversation is like a game of ping pong, and should bounce from one person to the other.

So the best speakers also share themselves too.

They tell stoires and antidotes. They explain things that have happened to them, or that they’ve learned about.

11) I’m not sure if I understand, could you explain it to me again?

Understanding one another lies at the heart of healthy and constructive communication.

Rather than feel stupid for not getting it the first time, a great conversationist is happy to ask for more clarification.

They’re led more by curiosity than ego. They want to know what makes someone tick — and that demands having a proper grasp on what they’re trying to tell you.

12) And how/why did you get into that?

It may be a job, hobby, or interest.

But asking this sort of question encourages more storytelling.

Certain questions tend to be closed, so the answer doesn’t last long.

It takes just a few words to reply — “Yeah, my day was great thanks” or “I’m an accountant”.

Expert talkers don’t just ask the standard things like “What do you do?”

They ask open-ended questions that give the speaker the opportunity to reveal more.

Tips to brush up on your conversation skills

Underneath it all conversation is actually just connection.

It’s about trying to form a bond, an understanding, or show an interest in another person.

Our relationships can rest on how well we manage to do these things. So how can we all get even better at it?

Here are a few tips:

1) Ask plenty of sincere and curiosity-led open-ended questions

As we’ve already seen, the quality of your questions is vital in creating interesting conversations.

Don’t just go through the motions to be polite. Ask the things you’re genuinely curious to know more about. Don’t be afraid to keep it interesting and ask more quirky questions too.

Having said that, don’t be too nosey…

2) Be sure not to pry

We have to be mindful of boundaries.

That also means considering that someone else’s may not be the same as yours.

Just because you would be happy to reveal details about your finances, don’t assume others will equally see it as no big deal.

The intimacy level you have established with someone makes a huge difference to what is, and isn’t, appropriate.

3) Consider your audience

The truth is that many of us do this unconsciously. But it’s important to read the room and know your audience.

Try to tap into the different sides of yourself that you think are most likely to unite you with the person you’re speaking to.

4) It’s not just about your words, it’s also about what your body is saying

You can ask lots of questions and still come off as pretty disinterested if your body isn’t matching up with your words.

Don’t forget those visual cues that show we’re engaged, like nodding your head, giving plenty of eye contact, and mirroring mannerisms.

Be sure to make yourself seem as approachable as possible through open body language.

5) Brush up on your active listening skills

A lot of us are good at talking, but less so when it comes to listening.

It’s not always something we would like to admit. But I’ll hold my hands up to the fact I can fall foul of some bad listening habits like:

  • Getting distracted
  • Interrupting the other person
  • Thinking about what you’re going to say next rather than focusing on what the other person is saying

Active listening is a good antidote to remind us of how we can better hold space for other people wheneve they’re talking.

Lost Your Sense of Purpose?

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Tina Fey

I'm Tina Fey, the founder of the blog Love Connection. I've extremely passionate about sharing relationship advice. I've studied psychology and have my Masters in marital, family, and relationship counseling. I hope with all my heart to help you improve your relationships, and I hope that even if one thing I write helps you, it means more to me than just about anything else in the world. Check out my blog Love Connection, and if you want to get in touch with me, hit me up on Twitter

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