How To Make Conversation - 5 Tips To Help You Stand Out & Be Memorable

Many of my readers ask me about how to make conversation. 

A conversation that feels natural and smooth.

Good news: These are learnable skills.

Having great conversation skills that you can "turn on" at a moments notice matter when you're:

• Applying for a new job and you're making small talk with the interviewer.
• You log on to the Zoom meeting early and your company's CEO is the only other person in the meeting room?
• You're on a first date where you know you want to make a great first impression.

The better you are with these soft interactions, the better your career, business and social life's trajectory will be.

And the best part?

These skills compound over time.

​Like investing in a 401K, the more connections you make, the easier it is to call up good friends, find jobs fast, and get introduced to more people who can change your life.

Here are 5 tips that you can use starting today to make better, more memorable conversations. 

Every one of these skills are effective individually, but when you stack them together, they become extremely powerful.

1. Anticipate Common Questions (And Prep Uncommon Answers)

We've all been at a party and that new person asks you: "What do you do?"

Most of us respond with a job description ripped right off of Monster.com.

Let's put ourselves in the shoes of the question-asker for a split second. 

• Maybe they're just being polite. 
• Maybe they're trying to get to know more about us. 
• Or maybe the company they work for is looking to fill a position you're perfect for ASAP.

When we respond to these common questions with common answers, we're not adding spice to the conversation. 

Unless the other person knows exactly what a Business Operations Analyst does, you're not giving them much to grab on to and respond.

There are a few common questions you should have answers for:

• "What do you do?"
• "Where are you from?"
• "How do you know the host/friend/whomever"
• "How did you meet your significant other?"

Let's take one of these questions and respond to it in a way that allows the other person plenty to respond to.

Common Question: "What do you do?"

Common answer: "I'm a copywriter."

Common response: "So you...uh...help people with trademarks?"

Uncommon answer: "I help businesses communicate the right message so that they can attract great customers."

Uncommon response: "Wow, so how do you do that?"

What works about this response: This answer gives the other person several things to grab on to:

​"What type of businesses?" "How do you figure out the right message?" "How do you figure out what a great customer is?"

You're making it EASY for them to engage with you.

(When it comes to conversations, easy is good.)

Action step: Take five minutes and create uncommon response to 3 common questions you're likely to be asked. 

The key to a good uncommon response:

• Goes beyond the basic information.
• Inject a little personality into your response.
• Make sure your response has at least one detail that the other person can respond to to further the conversation.

For more prepping great responses, listen to my podcast with media trainer Nicole Schwegman:

2. Read 'Em Like A Detective. Uncover Common Interests With People

When we find out we have something in common with each other, suddenly we tap into an ocean of things to talk about.

But how the hell do we figure out what people are into?

Sometimes it's teased out through conversation. 

"Oh! You're into Silicon Valley too? Have you seen the newest season yet?"

Discovering those commonalities through conversation is fine.

What if you don't have much time to uncover those connections?

Years ago, podcaster Tim Ferriss met author Tucker Max at a conference. Max was speaking on a panel and Ferriss came up to him after he got off stage.

Here's Tim Ferriss describing what he did right before he talked to Tucker Max:

"How did I go from Tucker’s [Jeff: First words to Tim being] “Who the fuck are you?” to drinking with him an hour later and having lunch with him the following day? 

Out of 40 people lined up, why did I make the cut? 

Simple: I made an educated guess and used language to reflect it. 

Here’s how it happened: I noticed Tucker had a big neck when he walked up to the panel seats. 

I therefore guessed he either 1) had trained in jiu-jitsu or wrestling, or 2) was a former football player who at least watched UFC. In response to “Who the fuck are you?” I answered “My name is Tim Ferriss. I’m writing my first book for Random House and used to compete as a fighter.” 

That was the lure. Tucker responded: “What, MMA?” Bingo. “I competed mostly in wrestling and kickboxing, but I train at AKA in San Jose with Dave Camarillo. Swick, John Fitch, and a bunch of the UFC pros train there.” A few minutes later, Tucker grabbed me to go drinking. 

Once again, it pays to know your audience, and being different is often more effective than being better."

Jeff's note: Notice how Ferriss didn't waste time trying to come up with the *perfect* thing to say, he quickly leaned into a possible shared interest in competitive fighting.

What if you could size people up in seconds so that you could bring up things that they're likely to WANT to talk about?

When it's done right, it's like magic.

Here's how to read people like a detective so that you can have a great conversation with them.

Three questions to ask yourself:

-What are they doing?

If you see someone drawing with sidewalk chalk, they might be artistic.

-What are they wearing? If they're wearing a hat of a Florida baseball team in Arizona, they might be a die hard fan.

-What is the context? If they're drawing with sidewalk chalk outside of a baseball game in Arizona with a Florida team in town to play the Diamondbacks, that paints a more complete picture of who this person is and what they (might) be about.

Things you might be able to talk to this person about: 

• Baseball
• Drawing
• Sports
• Art
• "Are you Banksy?"

All we're doing at this point is thin-slicing. We're trying to form a complete picture with minimal information.

Then, when we're in conversations with the sidewalk chalk wielding baseball fan we can test those assumptions:

"I couldn't help but notice you're wearing a Miami Marlins cap. You in town for the game?"

Maybe our thin-slicing was right, maybe not. The more times we use this muscle, the more tuned it will become over time.

Let's use some visual examples.

What thin-slice observations can you conjure up about this fellow in the vest?

Here are my observations:

• Sharp dresser. May care about style more than the average person.
• Has some interesting bracelets. I wonder if he knows Johnny Depp.
• Possibly into pocket watches, which is hipster level: 9000

If I happen to be into any of those things (or want to learn about them...cough pocket watches cough) these thin-slices give me plenty of topics to make conversation about.

Let's try another one.

What thin-slice observations do you have about this guy:

Here are my thin-slices:

• Probably into photography (shocker)
• Probably could give me beard growth tips
• I bet he has strong opinions about backpacks. (Almost no one would carry around a $1500 camera in a Jan-sport.

In conversation, I could bring up all these things and more, like: how does he think about framing a shot.

Remember, these are just thin-sliced assumptions. They could be wrong! The best way to test them is to mention them during the conversation.

"Oh, that's a cool backpack, what kind is it?"

One last time!

What thin-slice observations can you cook up about this chef:

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-Do the exercise, don't just scroll!
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Got yours?

Good. Here are mine:

• I could ask him about cooking, and more specifically the art of "plating" food. (Note the parsley in the middle of the plate)
• Could ask him about knife skills as a chef, something that I'm trying to improve.
• If you look close, you'll notice that he has a Michael Jackson tattoo. I could ask him about it. (Or tell him how, as a kid, I thought the Thriller video was a documentary.)

When we become a good detective, we're able to glance at a person and almost instantly have 1-3 things to talk about.

"What if I already know the person?"

Good news! If you're wondering how to make conversation with someone you already know a little about, it gets 10x easier.

You can still use some of the tips from above, but layer this on for good measure:

Recon.

I recently recommended recon to one of my private coaching clients.

This client was going to be around people that they already knew. 

I asked them to sit down with a paper and pen and write down common interests for each person.

Think of a Venn diagram, y'know that area in the center?

​That's the sweet spot where I want you to brainstorm.

If you're going into a meeting, or an event and you know a little about the people that are going to be there, jot down any shared interested that you two have. Then bring those topics up in conversation.

If they're talking about something that you don't know much about, you get to put on your curiosity hat. "Tell me more about spearfishing..."

If you're talking about something that only you're interested in, tread lightly, they may not care as much as you do. In this case, you can be 10x more passionate or describe your interest in an interesting way to "sell" them on it. (Review tip #1)

This same skill set is useful for having good conversations that don't fizzle out.

​The secret is "Thinking around the topic" for always having something to say.

3. How To Make Conversation The Easy Way (Without Struggling To Come Up With Things To Say)

The spokes method is one of the foundational things I teach my private coaching clients.

In a nutshell: The Spokes Method will help you connect with anyone on virtually any topic.

(Even if you don’t know much about the current topic.)

No more grasping for conversation topics! Yay!

Imagine a bicycle wheel.

In the middle, you have a hub, and radiating out from the hub are several spokes.

Now, imagine the hub as the conversational topic. 

The spokes are different, related topics that can be introduced.

Let's build on our examples from earlier:

Using Spokes, here are three things I could bring up with the chef about cooking:
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• "What's a recent favorite dish you've cooked?" (Note the phrase "recent favorite" means he doesn't have to scan his brain for his ALL TIME favorite. This decreases his mental processing power to make it simple for him to respond.
• "When you plate food, how do you decide where things go on the plate?" "Plating" is something that can make a meal look 100x fancier, just by being intentional about where the food is on the plate. I'd love to get his take on this.
• "What's a misconception people have about chefs. Does your family assume that you'll cook for all holidays?" Every job has a "behind the curtain" that is interesting.

Spokes is helpful because you're not having to do all the heavy lifting and think of new topics every few minutes. Most of the time, you're responding to things other people have said.

Watch this video for more Spokes examples:

​When we stack Thin-slicing, Spokes, and this next tip, we become a better conversationalist than 95% of other people.

4. Listen Beyond Their Words

Consider the following statement: 

"I'm going to work tomorrow."

Imagine it being said by these two people:

Person A: This person has been on vacation for 2 weeks.

Person B: This person just got hired after being out of work for three months.

"I'm going to work tomorrow."

Same words, but different feelings behind them.

When we're learning how to make conversation with anyone, it's important to keep an ear peaked for the feeling behind what people say.

This can clue you in on the best way to respond.

To person A: "Guess you'll have a mountain of email to catch up on, huh?"

To person B: "It must feel great to find a job that fits you after the last few months, huh?"

In each case, we're responding to their feelings about work. We're crafting "empathic statements" that speak to our audience's deeper emotions and feelings. This is a great way to rapidly build rapport with anyone.

For further reading on "empathic statements" read "The Like Switch" by Jack Schafer. 

In my experience, most people will always have some subtext just below the surface of the words that come out of their mouths. If you can key into that subtext, then you'll set yourself apart from everyone else they've talked to that day.

Action step: The next conversation you're in, try to assign a feeling to what the other person is saying.

Are they gleeful?

Are they anxious?

Then, try making an observation about that feeling to them.

Example: "Wow, you must be pretty pumped about that promotion!"

The tips you've learned so far will help you have better, more interesting conversations.

​But what happens when you get a rambler at a conference, or you just have to go?

5. Have An Exit Strategy...And An Exit McGuffin.

This one's pretty simple, but I see people float away from conversations or not know how to effectively end conversations. 

This results in them dying of old age while Gary over here rambles about his model train collection.

WE GET IT GARY, IT'S LIKE A TINY %$#ING  CITY.

So what can you do next time it's just time to GTFO?

1. Ask yourself this question: Is this someone I might want to follow up with in the future?
2. If so, what could be your "Mcguffin" (The podcast/book/article/movie/album/site/game, etc) to use as a reason to swap contact info? 
2. Vary script based on the answer to #1.

How about a couple of tasty tasty word-for-word scripts?

If you do want to follow up with this person at a later time:

"Hey, it's been good talking to you. I've got to run, but I'll send you that podcast link, what's your number/email/carrier pigeon address"

If you don't want to follow up with them:

"Hey, it's been good talking to you. I've got to run. Nice meeting you, <NAME>."

Alright! You now know how to have good conversations.

​Now get out there and practice!

Summary: How to make conversation exercises 

• Anticipate common questions (and prep uncommon answers)
• Uncover common interests with people (read 'em like a detective.)
• Use the spokes method to avoid struggling to come up with things to say
• Listen beyond their words (what emotions are they sub-communicating?)
• Have an exit strategy. do you want to follow up with this person?

Next Step For You

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