Six Tips for Good Conversations

You’re at a work function, a social event or on a hot date.  Either way, you need to be your most charming self.  The interesting conversationalist!  

So, how do you start a conversation with someone you just met or don't know well?  How do you keep it going? Most importantly, how do you avoid crashing and burning into that dreaded moment of awkward silence? 


Having a good conversation isn’t easy.  In fact, it might be a dying art as we spend more time communicating through our devices.   But conversation continues to occur in real life where we spend most of the time.  So let’s brush up!  Here are six tips on being a good conversationalist:

1) Ask thoughtful open-ended questions.  One way to connect beyond the superficial is to ask open-ended questions that invite people to tell more about themselves.  The kiss of death in conversation is often the one word answer followed by silence.  You get into that rhythm and you’re done!  To prevent this, focus on asking questions about how the other person thinks or feels about something they’re telling you.  For example, follow up what the person said with questions like: “What was that like?” or “What was going through your mind?”

2) Listen for real.   Show the other person that you’re listening, not only by nodding your head and “uh huh-ing,” but by actually listening.  This requires being mentally present because people can tell right away when their listener is distracted.  Ask open-ended questions (see #1) to encourage people to elaborate on what they’re saying, or reference what they’ve said later in the conversation to show you’re really with them.

3) Read a lot … about everything.   To improve your chances of having something to talk about with anyone you might encounter, it helps to know lots of stuff, especially on topics that different types of people can find relatable.  By stuff, we're talking knowledge of current events and subjects ranging from the serious (politics and business) to the fun (sports and what’s hot in pop culture).  This is where keeping up with the news or reading interesting books comes in handy. The more you know about a wide range of topics, the greater the chance you’ll have something at the ready to keep the conversation going.

4) Make observations.  When trying to start a conversation, especially with someone you don’t know well, it’s better to stick with safe topics because you really don’t want to offend right out the gate.   Safe topics are often those based on observations of your surrounding environment because you know you at least have that in common!  Weather is very safe, but rather cliché.  So, trade in “How about that rain outside?” for something like, “I’ve never been to this bar before, what do you think of this place?”  Or, if not too creepy, comment on what the person is wearing, perhaps something like, “Those are nice glasses. Mind if I ask where you got them from?” People love compliments and being asked what they think.  This automatically builds rapport which will then help you slide into a more interesting conversation.

5) Be a Learner.  A conversation is a great opportunity to learn new things, especially from someone who’s had different life experiences than you.   If there’s a subject you’re not that familiar with or something you’ve yet to experience, ask the person to share more about it.  It could be something like, “Why did you decide to rent versus buy?” because it so happens you’re trying to make the same decision.

6) Give your partner a helping hand.  As we noted earlier, the one word answer helps no one in a conversation.  So, it only follows that you should avoid giving one word answers yourself.  For a more comprehensive discussion on this tip, see a great article by Charlie Houpert.  In short, you need to answer questions in a way that hands the other person things they can say or ask.  Here’s an example:

Them: “Where are you from?”

You: “Well, I live in Seattle now, but grew up in a small town in the Midwest where everyone knows your name.  I miss it, but I love Seattle - the outdoor activities, the food scene, the diversity of people!”

Your answer reveals your values and your interests.  Now, the other person has a bunch of things they can follow up on based on what you said. 

With the holiday season approaching, you’ll be ready for any conversation - whether it's with the higher-ups at the office festivities, a newcomer to your friend's annual ugly sweater party or an eccentric relative at the family gathering.  If you’re so fortunate as to be the host of one of these fine holiday events, don’t forget you can make life easier by serving one of our bottled cocktails.  With nothing to mix or measure, you can focus all your energy on spending time with your guests.  Cheers to great conversations!