How to Get Lively Conversation Going with People You’ve Just Met

People with the gift of gab have that Midas touch of being able to say howdy to strangers and chitchat with anyone. Their most noticeable quality is how quickly they connect with the dozens of people we all encounter daily—salesclerks, ticket agents, taxi drivers, telephone operators, fellow elevator passengers, and a whole world of others. Long animated conversations with people they’ve just met seem effortless. When you too are adept at turning these strangers into acquaintances (and those you fancy into friends), you’ll know you are a graduate in the gift of gab.

“But what shall I talk about with these strangers?” you ask.

Psychiatrists have an annoying habit of always answering a question with another question. So I’m giving myself a promotion now, and Dr. Lowndes will do the same. My answer to your question is this question: “What is everyone’s favorite subject?”

Right, it’s themselves. But you already knew that. You continue, “But, if I don’t know them, I can’t just say, ‘Hi, tell me about yourself.’”

True. However, let me tell you how one stranger got me talking about myself in spite of the miserable mood I was in. In one hour, she transformed me from a stranger to a friend. I’ll always be grateful to my long-distance pal, Cheryl Mostrom, for inspiring this next Little Trick, which you can use with anyone you meet, anytime, anywhere.

How to Turn a Grumpy Stranger into a Gabber

One icy February day five years ago, I had a predawn flight from New York to Phoenix for a speech. At 4:00 A.M., I contemplated hurling my sadistic alarm clock out the bedroom window. But, lest it rub out some passerby, I decided against it.

There was no time for breakfast at the airport, and these days an “airline meal” is an oxymoron. A howling infant and his mom were my seatmates, so sleeping was not an option. As I watched the flight attendant pass out one puny packet of peanuts per passenger, I considered filching the jar of pureed apricot from the kid’s baby bag.

Changing planes at Midway Airport, I raced to the connection gate a good half mile away—just in time to sit on the plane for an hour while they deiced the wings. After a bumpy takeoff, the flight attendant passed out barf bags instead of peanuts.

The Arrival

As often happens, the event coordinator, whom I hadn’t yet met, picked me up at the airport. Meeting planners usually ask the obligatory, “How was your flight?” before moving on to grill me on every aspect of the program I’ve planned for them.

This time, Cheryl, from the law firm Fennemore Craig, who up until then was just a slight phone acquaintance, said, “You must have gotten up terribly early this morning. What time did your alarm go off?” She then inquired whether I’d had time to eat at the airport or if they served anything on the plane. On our walk to her car, she asked questions like, “Were the gates close together in Chicago when you changed planes?” “Was there much turbulence?” “Were you able to sleep on the plane?”

It was as though Cheryl had been filming me since the moment I staggered into my predawn shower. Had she seen me racing through the airport corridor at breakneck speed? Did she feel me itching to hurl my shoes at the security man who made me take them off?

I was flabbergasted at her sensitive queries because she only knew three facts: I took an early flight; I had to change planes in snowy Chicago; and the flight was an hour late. From those few clues, Cheryl envisaged what I’d gone through and realized I would want to get it off my chest. She demonstrated Emotional Prediction (EP) at its finest, and I felt an instant bond with her.

If Cheryl hadn’t asked those on-target questions as she drove me to the hotel, I would still have been grousing silently about my miserable trip. Instead, by the time we got there, we were both laughing about “the flight from hell.” I would have performed my entire speech in the car for her if it would have set her heart at rest that it was right for her group.

After I got to know Cheryl better, I complimented her on her insight about my experiences before I arrived. She said, “Leil, it’s the same thing you did when you sent me your preprogram questionnaire.” A preprogram questionnaire is a list of questions speakers send to clients so they can get to know the organization better before speaking for them. One of the crucial queries on the questionnaire is, “What has the participants’ day been like up until the speech?”

I haven’t seen Cheryl, who lives two thousand miles away, after that day we met five years ago. But we have remained phone and e-mail friends ever since.

A Surefire Technique Get a “Great” Conversation Going

Little Trick #19 is based on an irrefutable phenomenon in nature: Anything up close looks larger than when it is at a distance. This is true for experiences as well as for objects. For example, I didn’t feel Cheryl’s questions about my alarm clock or the proximity of the airport gates was small talk. Not at all. These hassles were still a big deal to me. I enjoyed getting them off my chest.

Here is the technique to get interesting conversation started—at least interesting to the other person. When you first meet someone, you know next to nothing about him. With very little effort, however, you can find out some trivial facts about his day. It can be as simple as asking someone at a party where he lives. If he lives at a distance, ask about his long drive. Ask questions like, “Was there much traffic?” “Were you driving on a highway or country roads?” “What’s the speed limit on those roads?”

It may sound silly to you, but this is not “small” talk to him. Why? Because details are still on his mental windshield. The time proximity makes them loom larger than they really are.

Inquiring about the traffic and speed limit the next day would seem trifling, even weird. But, at this moment, it is relevant conversation for him.

Questions about someone’s last few hours just kick-start the conversation. Soon the natural flow takes over and one subject leads to another. Take any seed of information you’ve gleaned. If you plant and nurture it, you will be amazed how quickly it turns into an animated discussion.

It Works Wonderfully with Friends, Too

It’s Wednesday. Your friend knows what time she woke up. What challenges she faced at work. Where she had lunch, what she ate, and with whom—and lots of other forgettable stuff.

To you or any of her other friends, these facts are did-dly-squat. However, they played a significant role in her Wednesday. That evening, she will love talking about them. By Thursday, she has forgotten Wednesday’s details, so asking then would sound pandering and foolish. For good conversation, catch someone’s trivia while it’s hot! Little Trick #19 isn’t just for creating conversation though. Since good friends are the only ones who talk about trivia with each other, chatting about your new acquaintance’s minutia gives the cachet of already being closely connected.

Soon after I discovered how well this Little Trick works on acquaintances and friends, I decided to see if it also works on people you see all the time, like a family member or someone you live with.

The high price of real estate in New York City necessitates some unusual living arrangements, so I have a male friend (Phil Perry) as a roommate. (I call him my “platonic male roommate.” He says we’re “friends with out benefits.” Same thing.)

Phil likes to take long leisurely walks through the city on Sunday mornings. When he returned from his next walk, I asked him dozens of tiny details, anything I could think of. “Phil, how was the temperature?” “Did you see many people on the street or was it deserted?” “Were there many stores open?” “Did you stop for breakfast?” “Where?” “What did you eat?”

He didn’t find my queries strange. He loved talking about his just-completed stroll—so much that I had trouble changing the subject.


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Little Trick #19
Ask People About Their Last Few Hours

  To get a new acquaintance (or an old friend) talking, ask about her day, preferably the past five or six hours. Visualize as many details as you can and ask about them. As far-fetched as it seems to you, she’s loving it because she is so close to the experience. Each particular question has a short shelf life, so use it while it’s hot.

     The formula is simple, and the conversational payoff is huge.