1. Great playfulness What do all great conversationalists have in common? They know how to play with the conversation. They can make their conversation fun. They do not take everything literally or seriously. If you are with a friend, and you get up to use the restroom, and they ask you, “where are you going?” You don’t always have to respond, “To the restroom.” Instead, you could say something less predictable and more playful, like, “it’s a secret…” or a sarcastic “I’m leaving, I’m sick of your attitude” or “who wants to know?” or “I’m going to go buy that girl a drink…not really, I’m not that cool.” Introducing play to a conversation opens the door for them to play along. For example, you might tell your spouse, “I’m going for a run…I’ll be back soon…” and if you add a fanciful hypothetical like, “unless I collapse from heat exhaustion…” or “unless I get attacked by stray dogs,” it becomes playful. This opens the door for them to play along with something like, “Okay…just in case, how much is your life insurance policy worth again?” or “If I don’t see you back in 20 minutes then I’ll call the search and rescue team to come find you.” Great conversationalists don’t always speak in literal terms such as, “the printer isn’t working well today.”  Instead, they may apply a fun metaphor, like, “The printer is being temperamental today” or “I’m currently fighting a battle with the printer… and the printer is winning. I might need reinforcements…”
  2. Great interest in them This is one of the easiest paths to great conversation (but many people don’t seem to take it very seriously). It goes beyond just listening to their long story about the time they outran a grizzly bear in Virginia. It’s about asking follow up questions. It’s about making comments about the events that they are describing. It’s about giving them attention and allowing the conversation to center on them and their interests. Be excited for them when they tell you that they just received a promotion. Sympathize with them when they tell you that they just lost their wallet.  Be interested in what is happening in their life. As the great Dale Carnegie once said,
  3. Great questions What’s the secret to maintaining a conversation? Ask great questions. Great questions are not always literal and information-seeking. If you’re out to lunch with your friend and ask, “How’s your job going?” – that’s a basic information-seeking question, and you’ll probably receive a basic answer such as, “It’s good.” Upgrade your conversation by thinking outside the box and taking a fun approach, like, “Have they made you CEO yet?” or “Is your boss still keeping you in that hamster cage?” These questions may appear playful on the surface, but they can still contain real inquiries about real topics. The literal questions can steer a conversation to different topics, but the fun questions can keep the conversation playful and entertaining. Fun questions are often rhetorical in nature and don’t always seek a genuine response. They are meant to introduce playfulness to the conversation so it doesn’t become stuck in serious-land. Maybe you see a coworker coming out of the building with a computer monitor. Instead of a literal, “What are you doing with that?” you could ask a playful hypothetical question, “Stealing office equipment again, huh?” Now that you’ve introduced a playful element, they may play along, with something to extent of, “You caught me!…hey are you looking for a monitor? 10 bucks and it’s yours!”
  4. Great responses Great conversation is like a great tennis match. If someone asks a poor conversationalist how their weekend was, they often reply with, “It was good.” Merely answering a question is not enough for great conversation. After answering, it’s your turn to hit the tennis ball back so the conversation can keep going. Offer your tennis partner something to play with (something to respond to). After saying, “it was good,” provide a reason why it was good, offer an example or share a story. Talk about how you feel about it. Then even ask a question back. It’s also important to match their energy. Did they just have a baby? Share in their joy! Act excited, ask them follow up questions. Great responses are sometimes playful. Maybe they complain to you, “My fingers are so cold…” And you could respond with something boring like, “that’s too bad.” Or you could offer something playful, “You’re always cold. Maybe it’s a medical condition. I think your blood vessels actually stop at your wrists and don’t go up into your fingers.” and then they may play back, “Maybe you’re right. That’s why my fingers are always blue. I should probably get checked out.”
  5. Great stories It’s not easy to entertain groups of people with interesting stories. The good news is that stories don’t have to be Pulitzer-Prize worthy for your listeners to enjoy them. In fact, some of the best stories are simple stories about every day events that may describe a unique twist or occurrence. Stories do not need to be elaborate and long. Did your pet dog accidently nibble on your new shoes? Did your toddler throw up at the grocery store? These events can make great stories, and most stories can be squeezed into 30 seconds. Great stories have some common characteristics. Make it a goal to include some or all of these story parts in your next story: Setup: For example, “That reminds me, I was just at that store two days ago and I saw the strangest thing.” Contrast against what normally occurs:  “I was watching this movie and I figured it was just going to be some boring “chick-flick”, but…” or “…and normally they would just get up and leave, but this time they…” Details:  Details add color and imagery to any story. Instead of, “and some girl bumped into me…” try “and some heroin-addict looking girl bumped into me…” Dialogue: Always add dialogue when you can. It’s easy and entertaining. “I was like, ‘When is this party going to end? This guy is so creepy!” Reaction:  “He bought me lunch… and I was stunned, I couldn’t believe it!” Turning Point: Great stories have turning points, like, “It was that moment where I felt…” Post Commentary: Don’t forget to comment about your story, “If it wasn’t for Joe, I don’t know where we’d be right now! Probably stuck in a ditch somewhere.” Limiting your story to 20 – 30 seconds may not seem like much time, but if they want to hear more, they will let you know!
  6. Great initiative Great conversation can only occur when at least two people are taking initiative. One sided conversations are never “great.” Simply responding to someone talking with, “oh yeah,” or “that’s neat,” or “I like it too,” is not a great conversation. State your opinions more often. “Wow, she needs to put down the mascara,” or “This is my favorite Italian restaurant of all time,” or “You look kind of like a homeless man today.” It also helps to add some superlative or definitive statements as well. They are simply more interesting than wishy-washy, passive statements. For example: “That’s the best coffee I’ve ever had…I can’t believe it’s so cheap.” “Easily one of the top five movies I’ve seen this year.” “I always read XYZ, it’s the only magazine that I fully trust.” And when you can, go beyond just stating your opinion. Add support. Add some commentary. For example: Opinion: “I’m excited to try this place.” Support: “I’ve heard great things. I actually haven’t had Italian in a long time. I’ve been on a Chinese kick lately.” Commentary: “I actually think my kitchen is starting to permanently smell like Chinese food!” Conclusion It’s important to remember that developing conversation skills is a lifelong journey. If you always aim to be perfect, you will lose out on the most important rule of them all; have fun. (Photo credit: Conversation courtesy of Shutterstock)