5 LINES THAT KEEPS A CONVERSATION GOING

5 Lines That Will Keep a Conversation Going

By Steve Errey

“So, um, what are you driving now?”

If someone asked me that at an event, I’d most likely turn on my heels and go find a wall to hit my head against. It’s not that it’s a dumb question necessarily, it’s just that it’s insanely dull and smacks of scraping the conversational barrel.

But we’ve all been there, right? Those moments when your head goes blank just as the last few words trickle out of the conversation, and you stand there in an awkward silence that makes you feel like a smudge on the social stage. You pile pressure on yourself to think of something smart, to tell an interesting story, or to reference something relevant, and you come up with a big fat zero.

So, in an effort to be helpful (it’s a new thing I’m trying), here are five lines to keep the conversation going.

1. Tell Me More About...

This one’s gold, not only because it offers you a simple way to leverage something you already know about who you’re with or something he or she has already told you, but because it feels flattering to have someone ask you to go deeper into a topic.

Tell me more about how that works. Tell me more about your thinking there. You mentioned [insert project/challenge/idea]—tell me more about how you’re approaching that. This line shows you’re interested in more than pleasantries and demonstrates your curiosity in learning about others.

Plus, you can use it for just about everyone—whether or not you really know about what they do.

2. What’s the Best Part of…?

What’s the best part of your role? What’s your favorite part of what you do? What lights you up in your business?

This is a personal favorite, because it adds a real splash of color when you’re in a situation that could be dry and grey. Asking this question takes people to their sweet spot—the place where they feel things flowing and the place where they’re at their best. And who doesn’t like to go there?

3. How Did You Get Into…?

People love stories. People have stories. People love to tell their stories.

Asking someone how they got into their line of work, how they got interested in their subject area, or how they crafted their role will open up all kinds of stories and discussion points.

And even if you get the classic “I just sort of stumbled into it” response, you can then ask what area they’ve always wanted to work in. It’s a conversational gold mine.

4. What’s Your Biggest Challenge?

There isn’t a business on the planet that doesn’t have its challenges. New competitors, integrating digital, recruiting the best people, or any one of a gazillion other factors are challenges that business needs to roll with. Asking about someone’s biggest challenge not only adds some serious meat to the conversational platter, but it might just help frame things or provide a fresh insight in the mind of the person you’re speaking to. Keeping the conversation going and being helpful? Love it.

5. What’s Your Favorite Cheese?

You might think that I’ve lost it at this point. Cheese? Well, while this appeals to my flippant and often ridiculous sense of humor, throwing in a curve ball cuts through the expectation that everyone needs to be “professional,” often makes people laugh, and gives a shot of energy into proceedings. A question like this might result in a story about a beautiful meal in Europe, it might turn into a debate about what the king of cheese is, or it might get into a conversation about a local farmers market.

You might be surprised; don’t disqualify the flippant as a conversation-starter.

The Golden Rule As a final point, the golden rule of conversation starters isn’t to rack your brain for another story or another bunch of details about a story you’ve already told. Nobody likes hanging out with that guy. You don’t need to be interesting (although chances are you already are), you just need to be interested.