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Small talk for introverts is a necessary evil.

As artificial intelligence increasingly pervades our daily interactions, mastering the art of small talk paradoxically becomes more valuable, not less.

Knowledge is rapidly becoming universal and immediate.

Whether it's a networking event, party, in-person business (like walking the floor as a trainer at the gym), or via online chat, meaningful unscripted exchanges are becoming premium skills.

Your ability to transition from casual chat to genuine human connection represents perhaps our most valuable social currency moving forward,  one that no algorithm can fully replicate.

Which sucks for socially awkward and introverted people like me.

Some people are naturally charismatic. If that's you, cool. Well done. Happy for you Don Juan. Seriously. Yay you.

For everybody else, I've studied this stuff so you don't have to.

There are loads of articles, videos, books, and online experts. But, really, two tricks have been enough to drastically improve my confidence in social settings and quality of interactions.

These two techniques are the 80/20 of charismatic conversation. They'll make you feel more prepared and less anxious. And they're so simple that I can teach you them in two minutes.

First, the only goal of small talk.

Then the two tricks. One for asking better questions. The other for responding to worse questions.

And finally, a 5-minute social prep exercise for you to do before any social event that makes you anxious.

The Single Goal of Every Conversation

Find something to geek out on together.

That's it. That's the whole game.

Not impressing them. Not avoiding awkwardness. Not seeming smart or funny or cool.

Call it the charisma paradox. The more you try to impress on somebody else your impressiveness, the less impressed by you they will be.

Find that one thing you both care about and can dive into enthusiastically.

When you internalize this goal, everything gets simpler.

The pressure drops. You're just on a mission to discover a mutual interest - sports, books, parenting hacks, travel spots, whatever. Once you find it, everything flows naturally.

Do you both like baseball? Movies?

Were you in the military? Did you just get back from Mexico? Are you oddly obsessed with artisanal honey?

The faster you find that connection, the better. Once you find it, explore it.

Next, how to get there.

Trick #1: Ask Open Door Questions, not Stop Signs

Some questions open doors to further discussion. Call them door knob questions. While others bring dialogue to an abrupt halt. Call them stop signs.

My son started playing with this other guy's kid at the pool yesterday. Me and the dude looked at each other and I knew we were in for some small talk.

I used to dread these interactions. Now I see them as practice.

After a bit of back and forth, there was a pause. I said, "so, do you have the kind of job where you go in at 9 and leave at 5 or is it the kind that really doesn't have stops and starts?"

I've basically asked "what do you do for work?" But in a way that invites him to tell more of a story.

He told me he's a management consultant. That he works regular hours but works with sports teams so travels sometimes for work.

Awesome. Cool. Now we're getting somewhere.

If all I did was ask what he did for work and he said management consultant . . . How do you follow that? "Oh. Cool. So, uhh, what kinds of projects do you consult for?"

But, because of how I asked the question, his answer gave me something to explore.

Stop sign question: What do you do for work?
Door knob version: So, do you have the kind of job where you kinda go in at 9 and leave at 5 or does it not really have stops and starts?

When you ask a question during small talk, try to give the other person permission to go deeper by tapping into an emotion. To basically say "nah dude, I actually want to hear this about you." The more they talk, the better chances you'll find something in common to double tap on.

I can't talk about management consulting. That's, like, the most boring job description ever. But travel is a thread I can pull on by asking "what's one of the coolest things you ever did on one of those trips?" 

Most people feel guilty talking about themselves.

You want them to.

You want to prompt them to tap into a memory which carries an emotion instead of just stories which are facts or, even worse, asking you the same question back instantly.

A few more examples:

Stop sign question: How'd you meet your wife?
Door knob version: How'd you and your wife choose your wedding venue?

Stop sign question: Where are you from?
Door knob version: What's your favorite thing to do in your hometown on weekends?

Stop sign question: How old are your kids?
Door knob version: What's the most unexpected thing you've learned since becoming a parent?

If part of your job includes sales via direct message on social media, this technique will improve your consultative sales conversations.

Daniel trains Jiu Jitsu athletes. He had a reel perform well and messaged new followers who engaged with the reel but didn't get much of a response.

A lot of people feel like scammy multi-level marketers when they do lukewarm DM outreach. Think of it as the beginning of a relationship. No different than meeting a dude at a pool or social event.

We workshopped Daniel's outreach on a call in my mentorship. Here's what we came up with:

Stop sign question: What's your current workout routine look like for BJJ?
Door knob version: Was there a moment you can remember where you knew you wanted to seriously train BJJ? For me, it was an episode of the Joe Rogan podcast where he talked about how hard physical training prepares you for life's challenges. I was going through some tough personal challenges and my buddy Jeff had been asking me to check out his academy for a while.

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This technique alone will transform your conversations.

But what about when you're on the receiving end of those dreaded stop sign questions? That's where the second trick comes in.

Trick #2: Conversation Threading

When somebody asks "where are you from?"

And you respond with "Toronto" . . .

You're providing one thread to continue the conversation.

They either know about your hometown or don't. If they don't, the conversation dies and it's hella awkward.

I'm in Mexico now. Literally everybody that I meet is either from Idaho or Colorado. I don't know why that is. And I know nothing about either of those places.

I do, however, likely have a bunch of values and interests in common with these people since we've both found our way to the same pueblecito in Mexico in the middle of March.

So, when somebody asks me where I'm from, here's how I respond:

"Home is Toronto. I've got a 7 and 2 year old and we live close to a river. My work forces me to talk a lot so I love to hide away a little and paddleboard. Then we spend four months every winter some place warm. What about you. What's your favorite thing to do in your home town?"

With the second answer, I provided them at least 6 threads to pull on and ended with a door knob question.

We could talk about Toronto, fatherhood, paddleboarding, or outdoor exercise. They might follow up with a question about how we manage education for my 7 year old for so long abroad. And I've opened up an invitation for them to ask about my work. Or, if they prefer, they can answer my door knob question and tell me about themselves.

Think of a thread as a hyperlink in a blog article.

If you follow that link, it's going to send you to another article leading to related articles.

A conversation is nothing more than an interconnected web of topics that all relate, similar to the web.

The topics are always there. You both need an avenue to naturally access them.

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That's it. Two techniques.

1. Ask door knob questions that invite stories.
2. Pre-prepare multi-threaded responses to basic questions.

As AI gets better at generating information and content, knowledge ceases to be scarce. What you know becomes less valuable every day.

Don't be nervous. Scarcity doesn't get solved, it gets displaced.

The new scarcity? Genuine human connection.

The time to work on your social skills is now. Especially if you're awkward like me.

You don't need to memorize 27 body language cues or force yourself to be an extrovert to reduce your anxiety in social situations. You simply need to prepare.

5 Minute Social Prep

Before any social event, I'll do five minutes of prep that drastically reduces social anxiety and increases the quality of my interactions.

It gives me the confidence to walk into a room of strangers and be more engaging.

Below's my simple exercise. Bookmark this page and do this exercise before your next event.

(Click here to download your own copy of the worksheet.)

Step 1: Anticipate the three most common questions you'll be asked.

Based on the event type, what are people likely to ask you? Write them down:

1. ___________________ (e.g., "What do you do for work?")
2. ___________________ (e.g., "How do you know ?")
3. ___________________ (e.g., "Where are you from?")

Step 2: Craft multi-threaded responses for each question.

For each anticipated question, prepare a response that includes at least 3-4 "threads" people can pull on:

Question 1: _______________________

My threaded response: ___________________________________________________

Potential threads I've included: ____________, ____________, ____________

Question 2: _______________________

My threaded response: ___________________________________________________

Potential threads I've included: ____________, ____________, ____________

Question 3: _______________________

My threaded response: ___________________________________________________

Potential threads I've included: ____________, ____________, ____________

Step 3: Prepare three door knob questions relevant to the event.

These are your lifelines when conversation stalls or you need to shift topics:

1. ___________________ (e.g., "If you could have dinner with two people from any point in history, who are you choosing and why?")
2. ___________________ (e.g., "What's the most unexpected thing you've learned about recently?")
3. ___________________ (e.g., "Do you have something you love to do on weekends when you're back in the town you grew up in?")

The beauty of this system is that after using it a few times, it becomes second nature. You'll start naturally crafting multi-threaded responses and door knob questions on the fly.

Remember: You're not trying to impress anyone. You're just trying to find something to geek out on together.

-Jon

P.S. Can you think of one person to text or email this article to? Somebody who might benefit from it or resonate with it. If so, please pass it along. Thank you.