4 Easy Steps To Make Conversations With Strangers Less Awkward

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4 Easy Steps To Make Conversations With Strangers Less Awkward

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Which tool is responsible for the most progress in our species? Is it microprocessors? Artificial Intelligence? Or the internet?

Each of these answers is right, but they’re incomplete. Microprocessors, AI, the internet, and every tool you can think of is a means for the real tool that has helped humankind progress in leaps and bounds: collaboration.

Collaboration was what put humans on the moon. It’s what enables humans to address humongous challenges like hunger, poverty, and the pandemic. It keeps us alive in the digital ether. And meaningful conversations are the scaffolding of collaboration.

Deep, constructive conversations turn strangers into friends, unite people to work for causes they’re passionate about, and lay the foundation for relationships that can last a lifetime. Such moments to hold stimulating conversations present themselves each time we meet a new person.

Sadly, they also often get missed. Over the past 100 years, almost every aspect—transport, computation, entertainment—has changed beyond recognition. But our conversations with strangers, like our schooling system, remain essentially the same. We often get asked the same safe yet dull questions, like:

What do you do?
Where do you work?
Where are you from?

Awkward silences and stalemates follow. Such small talk feels so painful that most of us would rather walk on burning coal than get dragged into it. As Bobby Powers wrote in an excellent article:

The sheer lack of imagination applied to most conversations makes it seem like our species only developed speech a few decades ago and we’re still trying to figure it out.

As a result, hundreds of opportunities to get to know others, build an intelligent network, and discover ways to collaborate and embark on fulfilling journeys, are lost.

This is exactly how conversations were for an introvert like me. But I’ve also learned from experience that they don’t have to be. Conversations can open our minds to the world if we open our hearts and minds to them.

Over the last year, I’ve had stimulating discussions with people I admire, which eventually spawned a podcast. These included conversations with:

  1. A career coach and prolific writer, who deleted all social media apps from his phone in front of me on our video call.
  2. A Venture Capitalist, who showed me his entire note-taking system.
  3. The Chief Product Officer at a startup that’s designing solutions for the Indian Air Force.

Such conversations left a deep impact on me, and, by their admission, on my guests as well. I realized that conversations don’t have to be awkward, nor do meaningful ones have to feel as effortful as wrestling a 900-pound crocodile.

Here are four steps I followed to make conversations with strangers an enriching experience for both of us. If you want to build or sharpen this skill, they might prove useful to you as well.

1. Conduct research in advance.

The reason we hold small-talk with strangers is to search for common ground. Finding it makes people appear familiar, and conversations with familiar people are less intimidating and awkward.

This is a common practice, but the outcomes are as predictable as the roll of a dice. Not finding common ground leads to awkward and painful silence. An easier and more effective approach is to search for something interesting about the other person. This enables you to ask them thoughtful questions that stoke engaging conversations.

For instance, I was keen to know how Akshay Ballal grew from an intern to a Chief Product Officer at FabHeads in just two years, and his take on 3D Printing since the startup is in that field. That led to a 90-minute conversation even though he initially said he had only 45 minutes.

Research the person in advance. It shows you genuinely care about getting to know them. Read their LinkedIn profiles. Browse the content they share on social media. Instead of looking for common ground, search for what makes them tick.

When you have a conversation on subjects that interest your counterparts, you come across as an interesting person yourself.

2. Start with a blank slate.

How do you feel when you’re in a conversation with someone who has an agenda? Words like “limited,” “restricted,” and “uncomfortable” come to my mind.

An agenda makes meetings productive. Conversations, meanwhile, aren’t supposed to be “productive.” The memorable ones flow freely and allow an exchange of ideas. which is why boxing them is a bad idea.

In the beginning, I didn’t know how much research on my guests was too much. I spent days browsing their profiles and making a list of 15 questions to ask. I thought this would show how diligent my research was.

But flitting between 15 topics in a 45-minute conversation became tedious for them. The conversation felt like an interrogation. It flowed superfluously while my guests’ real wisdom lay like sediment at the bottom of the riverbed.

Then I changed strategies. I identified just three questions I wanted to ask, shared just the first question with my guest in advance, and went with the flow. As a result, we could go deep into interesting subjects. And my guests got the freedom to express their raw, authentic selves to the listeners and me.

A conversation doesn’t fit in a box. It flows like a river, often in unexpected directions. Figure out your starting point, and then surrender to the flow instead of trying to control it.

3. Turn it into a game.

According to NPR host Celeste Headlee, a constructive conversation is like a game of catch, where you throw as much as you catch. You observe the throw’s direction, height, and speed, and adjust accordingly. Your counterpart does the same.

Many people assume effective listening means shutting up so the speaker feels heard. But think about the last time you spoke with someone who didn’t add much to the conversation. How did you feel?

You probably put a crazy amount of effort to keep the conversation going. You felt unsure whether they understood what you said or whether they were interested at all. The conversation probably felt draining and eventually ran out of steam.

I committed this mistake in the beginning as well. I got so engrossed in listening that I left my guests yearning for some engagement. Now that I know better, I just summarize what they say. This helps me understand their perspectives and lets them know whether their thoughts got conveyed effectively.

Lob meaningful questions, summarize the other person’s views, and add your perspectives in respectful ways. Most of your counterparts want you to engage as if you both are playing a game of catch.

4. Use the 30-second rule.

Alright. So your voice is important to make a conversation meaningful. But how long should you make others listen to you?

Some people use any opportunity to speak as a chance to let their thoughts run amok. They go off on tangents, and speak and speak until the listener loses interest. This dead-end is far from ideal. It also kills any possibility of a potential relationship. (Who wants to keep in touch with a bore?)

Instead, apply a constraint of speaking for 30 seconds at a time. And if what you want to say is too vast to condense in half a minute, pause after 30 seconds to check in with your listener. While checking in, avoid ego reinforcers like “Am I making myself clear?” or “Am I right?” Questions like “Does this make sense?” and “What do you think?” are better because they welcome listeners to open up with their views.

Resist the temptation to hog the mic. You will get your chance to share your thoughts. Maybe not today, but that’s okay. Sometimes one person gets more spotlight, but the scale balances out in the long term. Besides, if you have an important point to make, you can bring it up at the end.

Use the 30-second rule to prioritize what the listener needs to know over what you want to say. This constraint keeps you on point, encourages dialogue, and sets the stage for progress.

Summing Up

The fulfillment you experience in life relies to a large extent on the quality of your personal and professional relationships. And these relationships get built on the back of dialogue.

Conversations don’t have to be awkward. Nor do meaningful ones have to feel effortful. You can take a few simple steps to make them feel as comfortable as sex on a Sunday afternoon.

  1. Research people in advance. This will make them appear familiar, and conversations with familiar people rarely feel awkward.
  2. Go into the conversation blank. Know your starting point, then let the flow guide you. The journey and destination will be more enjoyable than if you enforce an agenda.
  3. Treat it like a game of catch. Switch between the role of a listener and speaker. Pose thoughtful questions, summarize what your counterpart says, and add your perspectives in a respectful manner.
  4. Prioritize what the listener needs to know. Stop speaking after 30 seconds so that you stay on point. And if you need to go on, check in with your listener first.

Like collaboration, conversations can open your mind to a universe of possibilities when you open your heart and mind to them.

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