How to be more interesting, no matter who you're talking to

Imagine: you’re on a plane when the complete stranger sitting next to you turns to you and says, “So, are you leaving home or going home?” Do you:

a. Give a short, polite answer and then put on your headphones and stare out the window for the rest of the flight.
b. Grudgingly engage in small talk for 5 minutes and then put on your headphones and stare out the window for the rest of the flight.
c. Try to shut down the conversation with a mournful, “I don’t have a home.” And then put on your headphones and stare out the window for the rest of the flight.$

I get it. Small talk is the worst. Making conversation with someone you couldn’t care less about feels like death by awkwardness. I don’t blame you for having those headphones ready. 

But sometimes small talk is unavoidable. Whether you’re at a networking event or a dinner party, sometimes you need to make conversation with strangers. So you might as well be good at it. That’s why today, I’m sharing four secrets to more interesting conversation, or, “How to master small talk.”

how to make small talk

1. To be interesting, you have to be interested.

Think about the most interesting people you know. What do they all have in common? Do they travel? Or have interesting experiences? Do they have unique ideas? Are they passionate or creative or courageous? 

All of those characteristics boil down to one thing: curiosity. Those people know that every new experience is an opportunity to learn. They’re constantly curious and interested, which in turn makes them interesting.

So take a page out of their book and remember that everyone you meet, no matter how boring they may seem, has some experience that you can learn from.

The key to being an engaging conversationalist is uncovering the other person's experience and being genuinely interested in learning from it. 

Remember, people love talking about themselves. Making someone feel like you're truly interested in their experience is the best way to be more relatable, and therefore more interesting.

2. Ask better questions.

If you want to have more interesting conversations, it’s up to you to ask more interesting questions. Because the fact is:

The quality of your conversations depends on the quality of your questions. 

Imagine you meet someone at a networking event in Chicago. One of the classic small-talk questions might be: “Where are you from?” And let’s say they answer, “I’m from Houston.” 

Now you have a couple options. You could do what most people do and relate it back to yourself, “I’ve never been to Houston, but I went to Dallas for a conference a couple years ago.” 

This, my friends, is boring. You probably don’t even care about your conference in Dallas, so why would it interest someone else?

What if instead, you went for a follow-up question that dug more into the person’s experience?
“What brought you from Houston to Chicago?”
“Is it really different?”
“Do you miss Houston?”
“So, can you get decent BBQ in Chicago?”

Sure, these aren’t deep, philosophical questions, but they engage the person you’re talking to and get them talking about more human topics, which will inevitably lead to a more interesting conversation. 

Another secret to asking better questions?

Only ask questions you actually care about the answer to. 

3. Small talk doesn’t have to be small.

Who said talking to strangers means you have to talk about the weather? No one (except maybe my dad) really likes talking about the weather. So let’s all agree to cut that shit out, ok?

That doesn’t mean that 30 seconds into meeting someone, you should start discussing their medical history.

But if you want the small talk to be more interesting, it’s your responsibility to steer the conversation into territory that interests you.

Let me give you an example. I was on a flight recently when the man next to me started up a conversation. We talked about where we were going and why, and then the conversation shifted to what we do for a living. I asked him about his job and he told me that he was a general practitioner.

Now, at this point of the conversation, I could have said, “Oh, ok. Cool.” and then sat in uncomfortable silence until one of us thought of another topic. 

But not this time.

You see, I’d been thinking a lot about work/life balance and the importance of our professional identities in relation to our general quality of life. Sure, it’s a little deep for someone I had just met, but I went for it anyway, and asked him how he found a good work/life balance with such a demanding career.

Yes, it might have been a personal question, but you know what? It opened up a fascinating 2-hour conversation about values, balance, purpose and what it means to live a good life.  It was one of the most interesting conversations I’ve had recently, and it all started with one question.

4. To be interesting, be prepared.

It always surprises me how few people actually prepare for small talk. It might feel a little awkward at first, but thinking ahead about questions to ask takes a lot of stress out of the art of conversation.

I do this before I go to networking events (which I desperately hate, but know are essential for my business). Before each event, I do two things.

Make a list of 3-5 questions and follow-ups to open up a conversation. 

The questions range from cold opens (“So, do you hate networking events as much as I do?”) to more personal follow-ups (“What made you finally decide to quit your job and work for yourself?”). Armed with these planned questions, I feel confident walking into a room full of strangers, knowing I have everything I need to hold a conversation.

Think ahead about what you want to learn and prepare questions about it. 

Remember, to be interesting, you have to be interested, so you need to get something out of the exchange as well. So, before any small-talk-heavy event, think about an area you’re interested in learning more about. (Helpful hint: Stick to areas that aren’t super personal. Please don’t go around asking strangers how to treat your cold sore.

Then, in conversation, bring up that topic and see if you can learn something about it from the person you’re talking to. For example, if I’m struggling with managing my administrative tasks, I might use a networking event to ask other entrepreneurs how they manage theirs. People love giving advice, and who knows? You might come away with some useful nuggets of wisdom.

And even if you don't, at least you aren’t suffering through yet another conversation about the weather. 

What are your tips for making better small talk?
Let's hear it in the comments below!