Eight Simple Conversation Techniques for Drawing People Out

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Every gent wants to be able to engage gracefully with other people, but some conversations can be more challenging than others—particularly with strangers and those with whom you don’t have much in common. How can you draw these people out in order to have a pleasant conversation? How can you convey authentic interest without coming across as fake?

Everyone encounters awkward conversations from time to time (see Embrace Awkwardness). It’s not the end of the world to realize that you don’t have much to say to someone, but it can be a shame because with a few simple techniques this rarely has to be the case. Below are a few simple tips that can be helpful in drawing people out.

Note that many of these tips have as much to do with an approach to people in general as they with specific conversation skills.  Self-help and self-improvement sites often include tips for making small talk or chit-chat, but not for engaging with people in conversations over the long-term. If you just need pass the time with someone sitting next to you on the airplane this might work fine, but most interactions happen with people we see over and over again. For these types of relationships, it’s important to view conversations in light of both the immediate conversation and the long-term relationship.

Here are eight specific ways to accomplish that goal:

1. Use open-ended questions. This is a fundamental skill that’s often under-appreciated.  Essentially, an open-ended question is one that invites someone to respond with more than a "yes," "no," or other one- or two-word response. The point is to get the other person talking about something they enjoy or care about—the things that are most likely to make them feel comfortable and enjoy the conversation. Some examples of open-ended questions might include:

  • "What got you started in medicine?" – Not "Do you like working at the hospital?"
  • "What’s your favorite part about watching a game at the stadium?" – Not "How many times have you seen this team play?"
  • "What brings you to an event like this?" – Not "So, come here often?"
  • "What do you think about the new U2 album?" – Not "Have you ever seen U2 live?"
  • "What were you doing when you heard about 9/11?" – Not "Do you remember when the Berlin Wall fell?"

And so on, and so on. Be careful not to overdo it lest you come across as insincere—it’s NOT about feigning interest or pretending that you’re fascinated by some mundane aspect of someone’s life. It’s about finding a topic that can facilitate a great conversation.

2. Give the person you’re talking with your undivided attention. This can be especially hard in today’s age of phone calls, instant messages, texting, or any of the countless other distractions which interrupt our days. If someone is in your office and the phone rings, make it a point to note that you can call the person back. It might be a small inconvenience, but everything you do sends a message about your priorities, and giving your company the attention they deserve shows them that you respect them (and their time) enough to focus on them exclusively. Along these lines, remember to make eye contact (not creepy eye contact, just enough to show that they have your attention) and don’t gaze out the window or fidget distractedly. Body language can clearly convey a message that’s entirely different than what you intend with your words.

3. Remember the seemingly small things that matter greatly to the other person. You might not think that they care if you remember the names of their kids or their wife’s favorite hobby, but it means a lot if you do. If the opportunity arises, to ask about the details of the other person’s life, especially those things you’ve never personally experience. If you work with someone, it’s easy enough to ask about how their new position is working out—that’s your own turf and probably something that’s easy to remember. Remembering that their five year old plays T-ball or that their high-schooler wants to join the military takes more effort and demonstrates that you view them (and their families) as a valuable people with unique interests, important relationships, and a life apart from whatever circumstances brought you together. Don’t force topics into conversations if it’s not relevant, of course—you’re not just trying to score points by showing that you remember.

4. Take active measures to remember—and USE—people’s names. Studies have shown that there is no sound that people enjoy hearing more than their own name, but this is far from the only reason to call people by name in conversations. Most notably, using someone’s name demonstrates that you recognize and affirm their individual identity. This might sound silly at first, but people want to know that view them as more than just some faceless cog in a machine. It doesn’t matter if it’s a waiter at a restaurant, your child’s teacher, a boss, or anyone else—using a name shows that you’re interacting with them as a person, not a position. Using someone’s name also has a practical benefit for you—it makes it much easier to engage someone that you encounter only occasionally. No one wants to run into someone in the hall (or even worse, have to ask for a favor) and start off by saying "hey, remind me of your name again." If you know that this’ll probably be the case, it can easily make you averse to speak with people for fear of embarrassment—so it’s much better to just learn, remember, and use their names up front.

5. Don’t approach conversations like one-night stands. If you have a fascinating conversation with someone and then never speak to them again, what’s the point? Just to pass the time engaged it witty banter? If you want to set the stage for a great conversation the next time you see someone, don’t just let them drop off your radar. Swing by and poke your head in their office, just to say hi–you don’t need a reason to say "Hey, I remember you said your Mom was sick when we talked a couple of weeks ago—how is she doing?" Think about how conversations fit into the long term picture, not just how to get through an awkward elevator ride or meeting.

6. Pause before speaking. This has a couple of effects: First it shows that you’re not in a rush to speak and that you actually care about what the other person has to say. You’re not just waiting for them to run out of breath so that you can share your own thoughts. Second, it prevents you from interrupting. By taking a calculated pause, you give yourself time to slow down enough to ensure that the other person has finished whatever thought they were trying to express. This may seem small, but it’s a small gesture that can go a long way towards developing an air of sincerity and authenticity. All the open-ended questions in the world can’t make up for someone who jumps in without waiting their turn to speak.

7. Find something to compliment. There’s nothing like positive reinforcement to give people a positive association with their interactions with you. This shouldn’t be empty words or flattery—just finding something nice to say that lets the other person know that you noticed something.  It’s important that compliments be specific, since anyone can say "great job!" after a presentation. Check out The Art of Giving Praise for more suggestions on giving compliments in a ways that are meaningful to others.

8. In groups, try to shift the conversation away from issues that leave participants out. For instance: if you’re at a work party and notice a coworker’s spouse standing at the edge while a couple of people talk about office politics, try to find a way to (gracefully) move the conversation into something where everyone has something to offer. Open-ended questions can be especially helpful in this regard. Remember that some people might be uncomfortable speaking in front of strangers and would rather just hang back—so again, don’t force topics. In most cases, however, people are happy to share their thoughts if they believe they have something to contribute and the other person actually cares.

Keep in mind that the focus for all of these tips isn’t just on social success or even productive conversations.  The point is to demonstrate respect for those around you and and ensure that your daily encounters leave others walking away feeling refreshed and valued. 

If you have other conversation suggestions or tips, feel free to leave them in the “comments” section!

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