5 Questions That Will Give You Depth In Conversation

The art of conversation is a dying one.

People’s attention spans have been hacked to pieces by billboards, smart phones, and endless digital pings… and deep conversation has been the primary casualty of our waning patience.  Which means (good news!) it’s never been easier to stand out from others who don’t bring anything to the table conversationally.

Like sex, conversation can be given little to no attention and be very surface-level and unfulfilling, or it can be given concerted effort and become a transformational tool like no other that leaves your head reeling for days.

With a bit of tact and awareness, your conversational skills can go from dead-fish to superstar in no time.

Whether you are at a lifeless office party, dinner gathering, or on a nerve-racking first date, these questions will equip you with the tools necessary to rock people’s worlds.

Want to be the most engaging person in the room?  Easy.

Here are five questions you can start asking more often to obtain real depth in your conversations.

conversation couple

1. What’s your story?

A great opening question that is open ended enough to inspire a real answer.

Some people have an instant answer to this question, whereas others might need a bit more of a helping hand.  To inspire depth in any conversation you often have to dig a few layers deep to get to the real heart of the issue.

In other words, “What’s your story?” in reality might go as follows:

You: It’s great to meet you Alex. So what’s your story?

Them: My story? Um… I’m not sure if I have one.

You: What has your life been like up until this point? Who is Alex really?

Them: Well, no one’s ever asked me that before. I grew up in California, moved to Vancouver for university to go to film school, left the industry in my 30’s, and now I’m in a kind of transitioning period where I’m trying to figure out the next steps of my life.

You: That’s an exciting phase to be in.  Transitions are never as simple as we’d like them to be.  Are you more excited, or nervous about the whole process?

Them: You are easily the most engaging person in this room. How did you say you knew the host again?

You: I don’t.  I just came here for the free food.

Game, set, match.  Instant best friends.

2. What are you passionate about?

One of the most cut-and-dry ways to get to someone’s most emotionally charged topics.

The word passion is loaded with preconceived meaning that people will project onto at will.  The receiving partner will do a quick scan of their memory bank and then tell you all about their volunteer work/surf school/years of travel that they have done.

Make sure that you receive their passion well by mirroring some of their excitement back to them so that they don’t feel like they’re out on a limb.  Feel their passion with them.  Let their story affect you and have it show.

3. If I really knew you, what would I know about you?

One of my all time favourite questions to ask people.

As with all of these five questions, this one is open-ended enough that it allows the receiving partner to go as deep as they want to.

In response to this question I’ve had people tell me things as seemingly surface as “I’m addicted to cheap milk chocolate” all the way to the other end of the depth scale with answers like “I’m a very sensitive person that often wonders how I haven’t gone crazy yet with all of the stuff that has happened to be in my life”.

Remember, if you are the one telling someone to metaphorically fall into your arms, you should have the courage to be there to catch them.  Make people feel heard, understood, and validated.  You both deserve the experience.

4. What in your life currently makes you feel the most fulfilled?

A variation on the second question that gets people thinking about what already makes them deeply happy.

Common answers include things like family, friends, career, and health milestones.

5. What’s a story of yours that you don’t get to tell often enough?

This one can be a bit higher risk than the others in that people either instantly have a story that they’re itching to tell, or they can’t come up with anything.

If it’s the former, great!  Indulge them and bring out every juicy detail of their story.  If it’s the latter?  No problem.  Ask one of the other four questions and dig elsewhere for conversational gold.

It Was Really Great Meeting You

A great follow up to question (in any conversational thread) to encourage more depth is “Why?”  As in, “Why did you feel that way?”, “Why is it that you enjoy surfing so much?”, or “Why are you nervous about your career transition?”

As with a lot of my articles on this site, this is a fairly introvert biased one. Introverts thrive in conversational depth. They are much more prone to digging deep than their more extroverted counterparts.  So if the idea of asking people such deep, probing questions makes you nervous then maybe it’s time you took a page out of the introverted handbook and realized that people enjoy going deeper in conversation.  Otherwise, how much chit chat are people really going to be excited about at your dinner party?

Go deep, you’ll be glad you did.

Dedicated to your success,

Jordan

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