How to Have a Great Conversation with Anyone

Posted by
Matan Magril
LivePerson Contributor
08/17/2015 - 12:05

We’ve all been there: stuck in dull conversation with no way out.

Whether you’re making new friends at a party, networking at a trade event, or working as a customer care professional, driving interesting conversation is a must. In all aspects of life — both professional and personal — engaging dialogue leads to more meaningful, memorable connections.

It’s not always easy, but don’t be a victim of awkward silence. Coming from my experience in customer care, the best professionals are the most personable. Whether you’re looking to up your conversation game for customers, for networking, or, hey, even for your romantic pursuits, below are a few tips that inspire great engagement.

Become a master conversationalist: 5 tips from the pros

1. Leave everyday small talk at home. Avoid filling the silence with questions we’ve all been asked countless times. I call these “conversation killers”: They are never memorable and, oftentimes, make it even more difficult to relate on a deeper level. Example A: How’s the weather? (I’m cringing inside.) Example B: How’s your week been? (Yawn.) While these are in fact open-ended questions, they are destined for simple, short answers that lead to silence or inspire yet another conversation-killing response.

If you’re on the flip side of these and similarly boring questions, try to answer in a way that guides the conversation in a new direction. Thought Catalog says it perfectly: “You need to take those questions that are GUARANTEED to be asked in the first five minutes (like “Where are you from?”) and answer them in a way that makes the other person want to continue the conversation.” And not just, “I’m from Israel. You?” See if you can find an engaging angle. For example, “I’m from Israel, but I’ve traveled all over. Where’s the most interesting place you’ve visited?”

2. Ask revealing questions. As previously touched on, think about your current interactions and ask yourself this: “Am I the best happy hour buddy/dinner date/road-trip partner [you get the point] that I possibly could be?” If the answer is no, then you may need a new approach. One way to take control of a conversation is to ask more specific, detailed questions that demand interesting responses. Take a moment to write down a list of questions that stimulate more interesting feedback. Here’s a few to get you started:

  • What did you do last weekend?  
  • What are you most excited for this coming summer? Any trips planned?
  • What was the best thing that happened to you this week?
  • Or, as  HubSpot suggests, “Ask everyone in the group which website they visit first when they get up in the morning.”

3. Get to the point. The best conversationalists know how to make a point — in as few words as possible. If you’re making a case for yourself or for a cause, ensure all interactions are adding value to the conversation and leveraging feedback from your counterpoint. Are his or her eyes glazing over? You know the signs. Steer the conversation in a new direction if he or she looks uninterested or aloof.  

            I’ll leave it at that.

4. Be a good listener. This may be the most important! In the words of Will Smith’s rom-com Hitch: “So when you leave the club, walk a little. Ask her what she thought about the show, what was her favorite photograph, why that one. And when she answers, don't be looking at her mouth. Don't be wondering what she looks like naked. Listen to what she is saying and respond.”

People love to talk about their personal and professional experiences — it’s human nature! An active listener looks interested (make good eye contact and maintain positive body language) and responds in a thoughtful way. There’s nothing worse than telling a story only to realize your companion was distracted by iPhone messages.

5. Stay current on your news. Anyone natural at the art of conversation is also an informed person. He or she can usually chime in on nearly any topic with relevant, insightful feedback. Carve out time for regular reading, including world, national, or trade news every day. Personally, I use Twitter to do a quick skim of what’s trending and to see what people are buzzing about.

Bringing the human back into digital customer service

As consumers, we love to shop online. But that doesn't mean we don't appreciate human support while we browse.

Hence, the growing appreciation for messaging apps and technologies. It’s convenient. It’s how we prefer to conversate with friends and family from a distance. But just because engagements are screen-to-screen instead of face-to-face or voice-to-ear, it doesn’t mean they can’t be meaningful.

It’s human impulse to want to engage with a live person — regardless of channel. Reaching the consumer on a more personal level is key to establishing and nurturing long-term brand advocates. Leading brands are finding ways to relate. For example, the Food Network has its own channel on Snapchat, featuring whimsical headlines like this “Just Wing It” screenshot on the left. 

Others have deployed live messaging to offer real-time guidance via one-to-one engagement. This is where conversational savvy is a huge plus. What’s more, with intelligence on their side, customer care professionals can add context to a conversation — ultimately making it more useful and meaningful.

If you’re interested in advancing your customer care game, below are a few helpful resources.

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