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Seow Yan Yi
Seow Yan Yi

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The 3 Step Approach To Make Initiating Conversations With Strangers Less Scary

You are at a friend’s birthday party and you see the cute girl from your school. You guys are taking the same classes together but had not talked before. She’s alone, getting some food from the table. This should be a great opportunity to strike up a conversation.

As you walk up to her, a million thoughts start racing through your mind. And the next thing you know she walks past you without even a glance… You missed your chance.

Talking to strangers is scary

Because you’ve never interacted with them before, you never know what’s going to happen.

How do you even start?

What if there’s an awkward silence after that?

Whether it is getting to know someone you fancy, attending a networking event, or the first day of school, meeting strangers is a part and parcel of life.

It’s 6:30 am and your alarm rings

You open your groggy eyes and try to draggggg yourself out of bed.

At this point, half of us will probably hit the snooze button.

But if you manage to persist through that first couple of agonizing minutes, wash up and make yourself a cup of coffee, it ain’t so bad anymore.

The first 60 seconds

The first 60 seconds of a conversation usually takes up 80% of our emotional anxiety and mental overthinking.

The hardest part is the initiation. Once we get past that first stage, we exit the world of imagination into the world of reality. And reality often is less scary than what’s in our minds.

As engineers, we use our brains a lot – yet overthinking is what also makes us hesitate and anxious. We start to use our most precious tool as an avoidance mechanism instead of a support.

So the trick here is to make it brainless and painless to start.

Step 1: Have a routine

Routines help you to lower the barrier of entry. You don’t need to think. Just do.

If you want to build a reading habit, you make it as easy as possible for you to read. Buy a book in advance. Put it on your desk in plain sight. Set a daily reminder for yourself. And when the clock strikes 8, you pull out your book to read without fail.

Routines for initiating conversations can be done in the same way:

Physically calm yourself – maybe it is drinking water, taking three deep breaths, or simply clearing the cluttered thoughts in your head.
Have a standard opening sentence and stick with that. At least you have your first few lines down pat.
Set yourself an internal timer. It could be 10s, 30s, 60s. Once you decide to approach someone you got to do it within that time frame. The longer you wait, the less likely it’s gonna happen.

Step 2: Disarm their concerns

Imagine a random dude walks up to you on the street and says:

“Hey! I’d like to have a chat with you”.

When we are so caught up in our internal world, we forget how we’re coming across to others.

In a random setting like talking to a stranger on the street, their first thought would be: What does this person want from me???

I once did a social experiment to try approaching random strangers wearing different attires.

Interestingly enough, the more casual my attire, the more it put people at ease!

When I wore formal clothes, folks thought I was a salesperson trying to sell them insurance and they kept a distance away from me. (No offence to friends in the industry)

When I wore smart casual, people were a bit wary but still willing to hear what I had to say.

When I approached people in a simple t-shirt, pants and slippers, and casually sauntered up to them to have a chit chat, I had some of the most open conversations.

I’m not saying you have to wear flip flops to a networking event… but just remember that people make snap judgements and they have a whole list of concerns in their minds. Consciously or unconsciously.

So make them feel comfortable. Be non-threatening. And let them know why you are here. This brings us to our third point:

Step 3: Go in with an objective

Nothing attracts an awkward conversation more than a conversation without an objective.

You become aimless and in the best case you start making meaningless small talk and in the worse case, you just stare at the person in silence.

People are busy. Even if you genuinely want to get to know them as human beings, most don’t have the time for that.

Objectives alone are not enough though. What’s even better is if you add specifics.

If I’m at a networking event, my general objective is to “expand my network”. But it’s too vague to be of any use.

A sub-objective could be to get 10 LinkedIn connection requests from the event.

Another sub-objective could be to find one common point of interest between you and the person you are meeting.

Objectives help you to stay focused and know what questions to ask, what topics to bring up.

So that’s it! Three simple steps for you to use in your next conversation with a stranger. Let me know how it goes for you in the comments below.

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