How to Strike and Carry a Conversation with A Stranger
Photo by Ingrid Vasconcelos on Unsplash

Do you struggle to strike and carry a conversation with a total stranger? If you do, I guess you know it by now. Most of the popular solutions to the problem, published by the top journals, don’t really work.

At least, not for beginners.

It’s easy to say:

  • be confident,
  • maintain eye contact,
  • nod when you listen,
  • and address them by their name whenever possible.

None of them worked for me. And until you (already) are easygoing, they aren’t likely to work for you either.

Here’s why:

  1. These generic tips don’t make you a better conversationalist. They only teach you how to pretend like one.
  2. And they fail to account for the inevitable element of anxiety.

The more confident you try to sound, the more nervous you get.

And when you (out of nowhere) start awkwardly staring at people while repeating their names over and over, it doesn’t make them feel relaxed. It makes them want to call 911.

Don’t worry. It’s okay. You are not unteachable.

I have a few tricks up my sleeves to get you what you want. These are far more effective, don’t cause excessive sweating, and won’t get you arrested.

Beat Your Anxiety No Matter Who You Talk To

Answer me this. Why is it so hard to talk to a stranger compared to talking to someone from your circle?

It’s because you don’t know them as well as your friends and family. That brings unpredictability. And our brains don’t like that. They want familiarity. Once you get to know them, the anxiety will evaporate.

Forget everything else. All you have to do is figure out who you are talking to and what they want.

No matter where you are and who you are talking to, it could be a job interview, a tinder date, or even a negotiation. Once you figure out people and their priorities, things get much less intimidating.

Find the ‘Why’ Behind the ‘What’

Listening to their words and rationale is essential. It lets you assess their thought process. Not many people do that. So if you do it, you instantly position yourself closer in the scale to the best communicators.

But why stop there? You can take it even further by reading the emotions behind people’s opinions and statements.

Not so long ago, I was approached by a prospective client. And when we started negotiating the price, I received a rather offensive racial remark.

According to him, just because I was Indian, I should not expect more than $5 per article.

Now, I had all the reasons to shut him out and go my merry way. But I didn’t. Instead, I chose to dig deeper. I asked him, “What made you think so?”

Here’s what I learned.

He already had his fair share of run-ins with cheaper Indian and Pakistani writers. He was addicted to the lower rates but not so much to the poor quality.

So, yeah, he felt cheated, and I (who had nothing to do with his previous experiences) was at the receiving end of his vengeance.

Now, I had his pain point. So it was time for the next move.

Don’t Get Trapped in Your Own POV

Most people who find it hard to strike and carry a conversation with someone make this mistake. They make it all about themselves.

Here’s what you need to know.

The only way you are going to get something across is to make the other person feel heard.

How to do so? Simple. Read others’ emotions instead of getting emotional yourself.

Chriss Voss, the ex-FBI hostage negotiator, terms it as tactical sympathy. As he quotes in his acclaimed piece, Never Split the Difference: Negotiating as if Your Life Depended on It:

Tactical empathy is understanding the feelings and mindset of another in the moment and also hearing what is behind those feelings so you increase your influence in all the moments that follow.

Again, reading their feelings isn’t enough. You have to convince them that you are listening.

That’s exactly what I did with the slightly rude prospective client.

I said, “It seems like you have had a string of bad experiences with cheap freelance writers. So it’s understandable that you don’t want to pay higher to hire another non-native writer.”

Not only did I summarize what he had told me, but I also sympathized with him for his troubles. Believe it or not, this little gesture had made him much more receptive to what I had to say next.

And once he saw the quality content published under my name and the materials I was producing for other clients, he agreed to a much better contract.

None of it would happen had I been rigid with my perception instead of trying to stand in his shoes.

Know When To Concede & When To Contest

There’s a common misconception that being the loudest one in the room is the true mark of a good conversationalist.

You must have known people who are (always) interrupting others mid-sentence, trying to one-up everyone, and talking about things beyond their comprehension. Do you find them charming?

The key to being a better communicator is to be open to the possibility of being proven wrong.

Too many people would turn a conversation into an argument they can’t win in a desperate attempt to protect their beliefs and self-image. Don’t do that. Or you will lose your grace while trying to save your pride.

And even when you have all your facts right, the other person might want to distract you by provoking your emotions or making unreasonable counterclaims.

It’s a trap. Fall for it, and you will come across as the bad guy despite being on the right.

What you should do instead is to welcome them to elaborate on their statements. Ask questions like, “What makes you so that?” or, “Why would you feel that way?”

Here’s why it’s a masterstroke:

  1. It makes them feel heard, opening them up t your counterargument
  2. It makes them expose their own logical inconsistencies that you can use against them

Don’t Pretend To Be Someone You Are Not

You might feel like you aren’t good enough, but trust me, you are!

It’s not your stamp collection or your taste in B movies that is the problem. On the contrary, it’s more about your ability to make them relatable.

So instead of trying to be someone else, focus your effort on being more relatable.

And how to do that? Tell stories, focusing on emotions and passions.

A chess player might not connect to your nack of fishing. But he will (most certainly) relate to your happiness after catching the biggest fish among your pals. That’s the same sensation he feels after defeating an opponent beyond his league.

Again. It’s not your stories. It’s how well you tell them.

How do you know that you are doing it right?

It’s when you don’t have to fake confidence, track your gaze, or worry about how you address someone. Once you have got the basics right, everything else will come naturally. It doesn’t go the other way around.