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How to Start [and End] a Conversation

The problem: We all want to be social, make friends, and develop good people skills, but we can’t predict how people will react to us, so we avoid interaction altogether.

The solution: There are a number of subtle tactics you can use to identify how someone will react to you and tricks you can use to carry a conversation or end it whenever you want to.

As far as I know, the only way to get good at being human is to talk to more of them. Social success depends on it. The more connections you make, the more the world opens up and, consequently, the better you typically feel about yourself.

But damn it if talking to strangers isn’t hard. Especially strangers who, as far as you know, would rather push you down a flight of stairs than give you the time of day.

In an act of self-defense, you close yourself off. It’s a reaction to the increasingly crowded world around us. Anyone who’s been to NYC can tell you that New Yorkers are the best in the world at pretending like other people don’t exist. That’s how you get through the day there without succumbing to sensory overload.

But if you go too far, you miss out on the great things that making new connections have to offer. What you need is some type of system that removes some uncertainty from the scenario. You need a way to get into conversations that you want, out of ones you don’t, and carry on the ones that show some promise.

Split-testing Your Social Skills

Earlier this year I started a small project called “Profiles of Risk” where I would walk around cities I was visiting and ask strangers to stop and answer a few questions about risk-taking on camera.

It’s a fun project and I plan to do more in time, but when I shot the first batch of interviews right here in my hometown of Portland, it was highly uncomfortable; flagging down someone and asking them to stand in front of your video camera is not necessarily the most enticing request to receive from a stranger.

A lot of people ignored me. A lot of people said no. One lady even told me, quite plainly, to leave her alone.

There’s no way around it. When someone tells you to leave her alone, it’s pretty embarrassing.

But after awhile, I started getting better. I learned how people liked to be approached—from the side rather than head on—and what kind of things I could say to keep their “stranger alarm” from sounding—a direct request followed by an explanation rather than a lot of beating around the bush. I tested lots of little tricks and, as I saw them work or fail, I’d keep or drop them.

Pretty soon, almost no one ignored me, fewer people said no, and I’d completely eliminated the problem of coming across as a pitchman.

It was great, but then I ran into a new problem. Sometimes, the people I’d engage would either turn out to be boring, incredibly longwinded, or assholes in disguise. I’d gotten pretty good at engaging people in conversation, but now I needed a way to get out!

So I started testing that process, too, and developed a few techniques. After just one long day of filming, I had a pretty good model to work from that could both get me into a conversation with a stranger and out of it if needed.

What I ended up with is a sort of four-part process to reference anytime I wanted a new interview for my video series—four questions I can ask myself to start and then lead a conversation so that it’s a good experience for both of us.

Today, I use it everywhere—in line at the grocery store, at a party, waiting for the bus. I’m a lot more sociable now, and it’s been a great experience for me. Here’s how it works.

Question #1: Do I Actually Want to Talk to You?

Talking to strangers is great, and you should probably try to do more of it, but there’s also an argument to be made for being a little selective. If the object is to have more good conversations and less awkward ones, then it’s a good idea to ask yourself a few questions before you start a dialogue to make sure it doesn’t turn into an uncomfortable monologue.

1. Do they show any signs of openness?

Body language says a lot about a person and you can get a good feeling of whether they’re open to being approached by how they carry themselves.

Where do their eyes go as they walk or stand? If they gaze around or look up to the sky, they’re probably open to being interrupted. If they’re fixed mostly on the ground, this probably means they’re more closed off.

How’s their general posture? Is it open and inviting or do they slouch a little? Slouching can mean you’re not so comfortable and less open to distraction.

What are their facial expressions saying? Furrowed brow? Detectable smile? Are their hands in their pockets (closed off) or out and visible (open)?

2. Is there a way out?

When you’re approaching someone for the first time, it’s uncomfortable. If there’s an easy out, then it’s less threatening for everyone involved. A conversation in a short line at the grocery store or a quick ride in the elevator is a good example. You have a captive audience, but not for very long. If something goes wrong—you get rejected or the person turns out to be rather unappealing—all bets are off after just a minute.

Keep in mind, though, that it’s hard to learn anything significant in these very low-risk situations. To become a skilled conversationalist, eventually you have to start taking some bigger chances.

Question #2: How Do I Open the Dialogue?

Do you have an objective? There’s nothing wrong with a little trivial conversation, but it’s harder to start than one that has an obvious purpose. When someone approaches you, what’s the first thing you think?

“What do they want from me?”

If there isn’t an obvious answer, you get uncomfortable and a little suspicious. If the purpose of the interjection is—or at least appears to be—clear from the get go, we put our guard down.

If you just want to have a conversation, you don’t need any kind of elaborate plan, but to break the ice it’s good to start off with an objective the other person can easily understand. Where you go from there is up to you.

So how do you do that? There are a few good ways.

1. Do you share an obvious commonality?

Are you wearing the same pair of shoes? Have the same color car? Waiting for the same bus? This can be incredibly trivial. It doesn’t matter what it is and, in fact, the more meaningless it is, the easier it is to at least get a response that can open a dialogue.

Obviously, this does come with a limit. “I see we’re both wearing pants” is unlikely to go far. Everyone wears pants—well, almost everyone—and it’s unlikely to reveal anything else. The same pair of shoes, however, can say quite a lot. It says you have a similar taste in fashion even if the shoes you’re wearing aren’t that uncommon.

“I see you have good taste in shoes. What are the odds? Pretty high I guess. Oh well. I’m Tyler, what’s your name?”

2. Is there an elephant in the room?

This is the easiest way to start a conversation with just about anyone. If you’re in a situation where everyone is thinking the same thing, but no one is saying it, you can have a roaring conversation going in just a few seconds by stating the obvious.

A few years ago I was in line at the grocery store when the woman in font of me started making a scene about a coupon that didn’t get scanned properly. She was yelling and cursing and stomping; it was ridiculous. Her daughter ran and hid behind the end of the check-out counter as if to say, “Oh no, Mom’s at it again.”

I turned around to a few other people in line and said, “How embarrassed do you think that little girl is right now?” Everyone had something to say about that. That moment of conversation also gave us the courage to let the woman know it was time to settle down and move on with life. I ended up standing in the parking lot for ten minutes sharing a laugh with one of the ladies in line with me.

3. Can you get them to start the conversation?

If there’s something obvious to be talked about, sometimes it can be fun to use your own body language—facial expressions, hand gestures, posture—to encourage someone else to start talking. This is one of my favorite techniques to use when negotiating. Of course, in most aspects of life, it’s better to just be direct. If you want to talk to someone, it’s your job to start.

Question 3: How do I Keep the Conversation Flowing?

Assuming that 1) someone opened up to you and 2) you actually want to keep it that way, your next challenge is to keep things flowing. You’ve built momentum and you don’t want to lose it. This is actually fairly easy as long as you keep a few things in mind and you aren’t bothered by feeling at least a little bit silly.

The best thing to remember at this stage is that you’re talking to someone brand new and neither of you are expecting to make any sort of deep discovery or connection. Random small talk feels silly, but it can save a conversation.

1. Are you asking questions or making statements?

Any time you’re ready to turn the pedestal over, make sure you end your piece in a question. It doesn’t have to literally end with a question mark, but you want to make sure you’re conveying to the other person that you’re ready for them to start talking. If you don’t awkward silence is the typical result.

And don’t just end with a question; make it an easy one. If they have to think too hard about what to say next, you’ll de-motivate them to keep things going. Try to stay away from closed questions (yes/no), and shoot for ones that require at least a little bit of explanation.

2. Are you talking less than 20% of the time?

In the words of Dale Carnegie, author of the classic How to Win Friends and Influence People, “No sound is sweeter to a man than that of his own voice.”

Live by this rule. If you want someone to like you, give him as many opportunities as possible to talk about himself. This is easy to do and actually quite enjoyable if you’re a naturally curious person.

Question #4: How do I End This Nightmare?

Ending a conversation when things are going great is easy. You simply stop, thank them for a great conversation and ask for/offer them some form of contact info so you can do it again.

Ending a conversation when the train has fallen off the track is a little more difficult, especially if the other person has enjoyed it more than you.  Still, there are few tactful things you can do to dismiss yourself from an exchange gone south quickly without doing too much damage.

Remember that the number #1 key in any exit strategy is to act quickly and decisively in order to avoid the dreaded awkward silence at the end of a conversation.

1. Enact the natural expiration.

If you followed the rule in question #1 by making sure there was an understood and arbitrary ending point for your exchange like there would be waiting in a short line somewhere, then when it comes you simply say, “Well, it was nice to meet you. I hope you enjoy the rest of your day.” Then you turn and walk away without looking back.

You’ve just escaped and there’s no animosity because it was always understood that the end of the line would likely be the end of the conversation as well.

2. Capitalize on a lull in energy.

This one takes some practice, and you’ll rarely get it on your first try, but the trick is to end the conversation during a natural lull, just before the break in silence turns awkward. This is hard because both of you will be fighting to avoid it, and if you don’t have a good exit statement lined up, you might say something that extends it rather than ends it.

Keep in mind that, due to the sunk cost fallacy, the longer you stay in a conversation, the more you’ll feel obligated to keep it going. This is why it’s important to pay attention early on and look for an out as soon as you lose excitement for the conversation. Don’t wait too long!

I meet a lot of new people, usually in captive settings where an appointment was made via email. For a situation like this, I always try to make it clear that the meeting will be 1 hour and then I have another obligation (usually true). This way, no matter how the meeting goes, there’s a natural end to it. And if it went well, then we can schedule another one later on.

Advice from Twitter

I also asked a few thousand of my closest friends on Twitter, Facebook, and Google+ for their advice. Here’s what some of you had to say:

I usually give a compliment on clothes/shoes etc or just a comment on the situation we’re in, i.e. long line, on train etc – @LFroment

A smile always works nicely. I’m partial to “Excuse me,” which may be a sign I’m more Southern that I thought – @soloconsulting

Ask if they know any good restaurants around. Preface with ‘I’m new here’. Could also ask directions. Or just say hi – @_Scott_Dinsmore

Does this look infected to you? ­– @graceface

Ask them about the area they live in. – @NigeHill

Well, my 3 year old goes up to random people and says, “Hi!” #toddlerwisdom – @dustiarab

I comment on their good energy then ask what was the best part of your day so far? – @joychristin

“Hi” + situational … I’m not a good enough actor to use anything else –  @KarolGajda

Ask a question based on something you observe with them: that’s a nice hat, where did you get it?, you seem like you know something about (whatever) can you tell me about it? – Magnus Petersen-Paaske

Usually a joke cuts the barrier (a funny one preferably) then an introduction. – Keith E. Daugherty

I also asked for a few ways to end a conversation…

Good talking with you, I’ve gotta dash. Or, excuse me, I’ve got to talk with so and so about blah blah blah. – Mary Jacobs

Start screaming, “SNAKES” as loud as you can while simultaneously running away, flapping your arms as if removing invisible serpents from your body. Works every time. It also has the beneficial side effect of having them not want to engage in the future. – Patrick Ray

Just say “I would like to end this conversation” then stare at them in the eyes until they turn around and walk away – Joel Runyon

I’d love to stay here and talk, but I’m not going to. – Cheryl Breuer

 

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