How To Have Great Conversations With Anyone You Meet

I used to imagine I would meet a cute girl standing behind me in line for coffee. I would turn around and smile at her. She smiles back. I say hi and we engage in conversation. Things are going wonderfully.

Then my nightmare will hit me. Some magic spell activates in my brain where I literally have no idea what to say next. We stare awkwardly at each other until I sheepishly turn around, pretending that we had never even talked, embarrassed at the whole situation.

These nightmares don’t happen with just attractive women but also with friends at a party and strangers at a networking event.

I become extremely anxious, thinking too much in my head what I’m going to say next. This led me to ask myself the hard question:

How do I have great conversations with anyone I meet?

This is the question I wanted to answer with writing my book on networking, attending dozens of events, and reading every “social skill” book I can find. But the most surprising method that has worked for me came from studying and performing improv.

In improv, two people start a scene based on nothing. As an audience member watching two people go on stage, we want to understand:

  1. Where are they?
  2. What are they doing?
  3. What is their relationship?

The faster the performers can answer this question, the more the audience understands what is going on. So how do you answer these three questions in the first line?

Here’s one line that my improv partner gave me when we were starting a scene together:

[southern accent] “Joe, get over here and put sunscreen on my back so we can play volleyball with the crew.”

One line gave me SO MUCH to work with and build off of in the scene.

  • I know that my name in this scene is Joe.
  • She’s asking me to put sunscreen on her back so I’m most likely someone she trusts. Maybe a boyfriend, husband, close friend, family member.
  • Sunscreen implies that we are outdoors, probably on a beach because we are about to play volleyball.
  • Crew represents our group of friends. It sounds like we are on the side alone a bit distant from the group getting ready to join the fun.
  • She has a southern accent so we’re probably, you know, somewhere in the south.

Now I can proceed with the improv scene with many different options.

I could play the role of her caring husband taking care of her. I could play the role of her overprotective mom who says “Finally you listen to me. Now you’re not going to get skin cancer!” I could play the role of a friend who does a small favor, and so on.

Everything my scene partner gave me now were beautiful gifts that I could work with, which is the biggest lesson I learned when having conversations.

You want to consistently give and receive amazing gifts to and from your partner.

No, I’m not talking about physical gifts.

I’m talking about verbal gifts.

These gifts give the other human more opportunity to easily make connections with you. Then you can listen for the gifts they are giving you and play off of that.

Here’s a real world example.

Conversation #1 — Rob meets Joanna for the first time at a friend’s social gathering.

Rob: Hi Joanna. Nice to meet you. How’s your day going?

Joanna: Good. Yours?

Rob: Good as well.

Joanna: …

Rob: Nice weather here in San Francisco, huh?

In this conversation, Rob asked Joanna how her day is going. She responded and although she asked a question back, it wasn’t a strong enough alone to keep the conversation going. Rob gave a gift of talking about the weather, but that is a weak gift that isn’t interesting enough for Joanna to accept and easily play off of.

Conversation #2 — Rob meets Joanna for the first time at a friend’s social gathering.

Rob: Hi Joanna. Nice to meet you. How’s your day going?

Joanna: Hi Rob! My day is well going well. I spent the morning at Philz Coffee reading a book called Nonviolent Communication. Then I went to practice with my hip-hop team for our performance next month and now I’m ending the day meeting new friends!

Let’s pause here. Joanna gave us a drastically better answer and now we have so many directions we can take.

The verbal gifts she gave us were: Philz Coffee, a book called Nonviolent Communication, and practice for her hip-hop performance.

We can ask her so many questions that get deeper into who she is with each of these gifts.

Philz Coffee:

  • What Philz coffee do you normally go to in the city?
  • Do you normally go to Philz Coffee every Sunday morning?
  • How many hours did you read your book at Philz Coffee?
  • What is your go-to drink at Philz Coffee?

Nonviolent Communication Book:

  • What is Nonviolent Communication about?
  • What do you think of the book so far? I’ve read it last year to learn how to be a better romantic partner. (This is assuming you have honestly read the book. Notice how you are also giving her a gift to work with.)
  • What is one lesson you took away from reading the book so far?
  • What made you want to read Nonviolent Communication?

Hip-Hop Performance:

  • How long have you been dancing hip-hop for?
  • What kind of performance are you dancing for?
  • What are some of the songs you are choreographing the dance to?
  • How much have you practiced your choreo?
  • What’s your favorite part about practicing for your hip-hop performance?

These are some of the infinite amount of questions you can continue the conversation with.

The point of having conversation is to get to know the other person and give them the opportunity to understand you better.

  • What kind of person would go to Philz coffee on a Sunday morning to read a book?
  • What does her choice of reading Nonviolent Communication say about her personality and interests?
  • What does her practicing for a hip-hop performance reveal about her hobbies and upbringing?

Let’s keep this conversation going.

Conversation #2 (cont.) — Rob meets Joanna for the first time at a friend’s social gathering.

Rob: No way. What do you think of the Nonviolent Communication so far? I’ve read it last year to learn how to be a better romantic partner.

Joanna: It’s really great so far. I’m only halfway in and I’m already using the scripts on a coworker that I used to argue with often… and it is actually improving our relationship.

Rob: Wow. That’s amazing!

Joanna: Yeah it really is. What did you learn from the book that helped you with your romantic relationship?

Pause right here. This is getting great. Let’s recap what happened.

Joanna shared her honest opinion on the book and gave another gift of how the book helped improve the relationship with her co-worker.

Rob reacted honestly and dropped a gift about his experience reading the book.

Joanna acknowledged Rob’s reaction and picked up on Rob’s gift, then asked him about his experience.

Now both people are revealing more of themselves to each other. This is super important. Yes, you want to ask good questions. You ALSO want to give your own verbal gifts so that she can accept them.

Giving and receiving gifts can help make you connect with the person on a deeper level.

Let’s take another example.

Conversation #1 — Mike meets Jon at a friend’s housewarming party.

Mike: Hey, my name is Mike.

Jon: Hey, my name is John. Nice to meet you. How do you know Sally? (the party host)

Mike: We met at work.

Jon: Oh cool. Where do you work?

Mike: Google.

Jon: Nice. what do you do?

Mike: Business Operations. What do you do?


What happened here? Why is this so boring?

You are not giving Jon any gifts (or enthusiasm) to work with.

Tell us how you met Sally at work. Get specific. Tell the story. Give gifts.

Let’s try this again.

Conversation #2 — Mike meets Jon at a friend’s housewarming party.

Mike: Hey, my name is Mike.

Jon: Hey, my name is John. Nice to meet you. How do you know Sally? (the party host)

Mike: We met because I host board game nights with some Googlers after work. Last Saturday, we all played Monopoly for 6 hours while getting drunk off wine. It was one of the most unexpected and epic nights of 2017.

PAUSE. Much better!

What are the gifts that Mike is giving Jon?

  • Board Game night
  • Googlers
  • Monopoly
  • Wine
  • Unexpected and epic nights of 2017

This one data point can help Jon understand more about what kind of person Mike is.

What kind of person hosts board game nights? What kind of person works at Google? What kind of person plays Monopoly for 6 hours while getting drunk off wine, and says how it was an amazing night?

Mike gave Jon so many gifts to work with that he can take the conversation in any direction that he’s most curious about.

When you’re in a conversation, look out for gifts. Make sure you are giving gifts.

There should be an OVERFLOW of gifts.

Don’t accept all of them.

The best conversations I have had are the ones where you and the other person have TOO MUCH to talk about. You have too many gifts to give and receive — what a great problem to have.

I hope you make your next conversation a “gift.” :)

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