David Morin

4 steps to make interesting conversation with anyone

How can we be sure that we don’t bore people? Is there a way to always know that you’re interesting to talk to?

Today, I want to show you the system I use to make truly interesting conversation with anyone.

A few years back, I was going through all those conversations I’ve had where I’ve clicked with people and it felt like we could talk on forever. I compared them to all those conversations where it’s like you just talk out of courtesy and no one is really interested in keeping the conversation going.

I tried to find a pattern. Is there a universal way to make a conversation really INTERESTING?

Here’s what I found out: There is no topic that’s automatically interesting to talk about. The key to an interesting conversation is this: You want to find mutual interests.

When you find a mutual interest to talk about, time flies and you’ll both think the conversation is interesting. This is where you connect and bond with each other.

I was able to figure out a system that I put to the test. It turned out that it’s possible to find mutual interests and make truly interesting conversation with almost anyone. Here’s it is, step by step:

Step 1: I ask myself what the other person might be interested in

Whenever I meet someone and start thinking of how to start a conversation with them, I make a guess or an assumption about what they might be interested in. I call this my “interest hypothesis”.

After just a few minutes of conversation with a person, we can make some decent assumptions. Our assumptions might be wrong, but that’s OK because we’re going to put them to the test.

Here’s an example from a conversation I had last week

One girl I met last week told me that she works as an assistant on film sets. I know close to nothing about big movie film sets. But thanks to making an assumption, I could still turn this into an interesting conversation. I assumed that she’s also interested in filmmaking in general.

Because I record a lot of things for SocialPro, I obviously think that’s interesting too.

So I asked her if she films anything herself. Not too surprisingly, it turned out she did. We had a really interesting conversation about camera gear and filmmaking in general.

Another guy told me that he worked as a coder. It’s a fair assumption that a lot of people who are coders are interested in computers in general and maybe even in technology overall. Personally, I don’t know much about coding. But that doesn’t mean there’s nothing to talk about! I think it’s exciting to talk about artificial intelligence and the future of technology. So my hypothesis is that because he is a coder, he might also be interested in that. If so, that would be a mutual interest.

So I wanted to lead the conversation away from coding, which doesn’t interest me much. I wanted to find a related subject I’m interested in that he might also be interested in. So I said, “I saw that Google Deepmind made an AI that beat all other chess AI:s”. (This is super nerdy, I know. But that’s the entire point of common interests: To be able to bond by nerding into something you both like.)

It turned out that he, just like I guessed, was super interested in AI. Because of that, we had a long and interesting conversation on that subject.

Exercise: What might you have in common with these people?

Here’s a small exercise to get you used to step 1, making assumptions that we can later test.

Let’s say that you meet this person and she tells you that she works in a bookstore. Just by using that tiny piece of information, what are some assumptions we can make about her interests?

emma conversationI’d say…

  • Culturally interested
  • Prefers indie to mainstream music
  • Likes to read
  • Prefers to shop vintage
  • Vegetarian
  • Prefers going by bike over driving
  • Environmentally conscious
  • Lives in an apartment in a city, maybe with friends

Again, these assumptions might be dead wrong, but that’s OK because we can put them to the test.

Here’s another one to practice with:

jessica conversationYou meet this woman and she tells you that she works as a manager at a capital management firm. What assumptions can we make about her?

Obviously, these assumptions will be very different from the girl above.

I’d say…

  • Interested in career
  • Reads management literature
  • Lives in a house, maybe with her a family
  • Health-conscious
  • Drives to work
  • Has an investment portfolio so is concerned about the market

Here’s the last one:

tyler conversationThis guy tells you that he works in IT security. What would you say about him?

I’d say…

  • Computer savvy
  • Interested in technology
  • Interested in, well, IT security
  • Plays video games
  • Interested in movies like Star Wars or other sci-fi or fantasy

As you notice, our brain is really good at coming up with assumptions about people. Sometimes, it’s a bad thing, like when we’re being prejudiced. But here, we’re using this extraordinary ability to connect faster and make interesting conversation.

Step 2: Mutual interests – What might we have in common?

Now we’ve been thinking about what others might be interested in.

It’s time to ask ourselves, what is interesting to us that we also might have in common with them?

It doesn’t have to be the passions of our lives. Just something that you enjoy talking about is enough for an interesting conversation.

Step 3: Testing our assumptions

Let’s revisit the girl in the bookstore that we met above.

I don’t know that much about books, at least when it comes to non-fiction. But I do enjoy talking about environmental issues, and I hypothesize that she might too. So I ask something to move the conversation in that direction:

“What’s your view on e-readers? I guess they have a lesser environmental impact than books, even though I prefer the feeling of a real book”.

Maybe she says “Yeah I don’t like e-readers either but it’s sad that you need to cut down trees to make books” (Or whatever).

Step 4: Judging their reaction

Judging by her answer, I will know if she seems to be concern about environmental impact, and we can now segway into talking about that.

Or, if she seems indifferent, I try another topic. (For example, talking about if she bikes to work and what bike she could recommend. I’m looking at bikes right now so that’s something I would be interested in talking about.)

Making any conversation interesting, in summary:

Step 1: Ask yourself what the other person might be interested in

Step 2: Mutual interests – What might we have in common?

Step 3: Testing our assumptions
– I move the conversation in that direction to see their reaction.

Step 4: Judging their reaction
– If they are indifferent, I try their reaction to some other subject
– If they respond positively, we can delve into that topic.

It’s when we combine our interests with others that the magic happens.

When you’ve found something you have in common, you can feel confident that you’re making interesting conversation. You’re now light years ahead of everyone that tries to make an interesting conversation out of just their own or the other person’s interest. It’s when we combine our interests with others that the magic happens.

Read more: How to be more interesting to talk to.

How to start a conversation

Looking at this scheme, there are several factors that affect how comfortable we feel in social situations. They all affect each other – and that’s good news.

nervous

If you, for example, improve your conversational skills, that will also help you feel more confident, as you will trust yourself in knowing what to say next.

You could ALSO do specific exercises to feel more confident in social situations, and then it would become easier to come up with things to say. In this guide, we will focus on both conversations AND confidence. Let’s start off with the conversation.

I will give you six universal questions that you can use almost every time you start talking to someone. I’ve designed these questions specifically to be as effective as possible for getting a smooth, interesting conversation going.

By memorizing the questions, you will always have a conversation to fall back on. That will in itself make you feel more confident when talking to someone you just met.

Important

  • In between the questions, the conversation might take off in any direction – and that’s a good thing. But whenever it’s running dry, you can go back to the next universal question.
  • You shouldn’t fire these questions off as in an interview, but see them as something to come back to. In between them, you will answer the other person’s questions and tell things about yourself whenever it feels natural.
  • Questions used in examples like these might sound corny when you read them. That’s often simply because they are read in a different voice than they are intended for. Imagine them being spoken in a relaxed, casual way.

quest

CONVERSATION QUESTIONS

When I start talking to someone, I obviously first present myself:

– Hi, I’m David. How are you doing?

Starting off from the first line, I’m keeping the conversation simple. The simpler you keep the initial conversation, the better it will flow, because it decreases the risk of pauses and awkward silence.

A common mistake people do is trying to come up with something clever to say already in the initial conversation. However, an interesting conversation is not created through smart comments; it’s created by talking about something you both enjoy discussing. And that is what these questions are designed to create. Let’s continue!

– How do you know people here?

This question can be used in most situations where you meet strangers. Let them explain how they know people and ask follow-up questions relevant to what they’re saying. This question is designed to help gradually transition into a more personal conversation, as it obviously would feel weird to start talking about personal stuff the first thing you do.

– Where are you from?

This is a good question because it’s easy for the other person to answer and talk about. It’s useful even if the person is from the same town – you can talk about where in town and what it’s like living there. Perhaps you have something in common that you can both relate to about the area.

– Do you work/study?

I ask about either work or studies depending on how old the person is.

Some say that you shouldn’t talk about work with people you just met. And I agree that it’s boring to get stuck in job talk. But knowing what someone is studying or working with is important for getting to know him or her, and it’s often easy for them to expand on.

If they are unemployed, just ask what they would like to work with or study. When you’re done talking about work, it’s time for the next question:

– Is it busy or will there be time for vacation/holiday?

When you’ve arrived at this question, you’re past the hard part. No matter what they reply, you can now ask my favorite question of all categories:

-Do you have any plans for your vacation/holiday?

Now you’re tapping into what they like to do the most. They think about positive things and it’s interesting for them to talk about. Even better, here’s where you might find mutual interests or similar places you’ve been to. Even if they don’t have any plans, it’s now natural to talk about how they spend their free time. It’s often possible to find similar interests here.

Click here to read 301 small talk questions to ask friends.

CONVERSATION EXAMPLES:

Scenario 1:

YOU – Do you have any plans for your vacation?

STRANGER – I don’t have any plans yet actually. Last year I went to Hawaii.

[You can now ask about how Hawaii was and talk about other vacation places you’ve perhaps both been to]

Scenario 2:

YOU – Do you have any plans for your vacation?

STRANGER – I’ll probably just stay at home.

YOU – I see, yeah so did I my last vacation and that was pretty nice. Do you do anything special on your free time?

STRANGER – I’m mainly reading/working on my house / working on this and that project / hanging out with my friends.

[You can now ask more about whatever the person is doing and look for mutual interests here]

Scenario 3:

YOU – Do you have any plans for your vacation?

STRANGER – No, actually I don’t…

YOU – I see… Yeah, same here. I use to end up mainly watching TV series when I’m having time off though. Do you watch anything?

[This example shows that even if they don’t have any plans AND aren’t good at making conversation, you can still look for similarities in how you spend your free time]

Scenario 4:

YOU – Do you have any plans for your vacation?

STRANGER – Yes, I’m planning a Euro-trip!

[You can now ask where in Europe the person is going if he’s been there before, let him or her know where you’ve been on your vacation, relate to the countries the person’s been to and so on]

As soon as two people find similarities or mutual interests, the conversation becomes interesting. The “small talk struggle” is over, because it’s easy to talk about something you’re both interested in or know about.

Why am I talking so much about finding similarities? Because A) Conversations become easier when you do and B) It’s when two people find similarities they really start liking each other.

“Friendship is born at that moment when one person says to another: ‘What! You too? I thought I was the only one.”

-C.S. Lewis

My conversation recipe

This is what my recipe looks like when I just start talking to someone:

  1. Ask very simple questions.
  2. Ask follow-up questions and mention related things about yourself.
  3. Dare to break the rules. You can and should follow whatever direction the conversation takes, but whenever your mind goes blank, you can go back to these questions.
  4. Try to figure out what the person likes to do and if you share any similarities.

(¯`·._.·(¯`·._.· CHEAT SHEET ·._.·´¯)·._.·´¯)

– How are you doing?

– How do you know people here?

– Where are you from?

– Do you work/study?

– Is it busy or will there be time for vacation/holiday?

– Do you have any plans for your vacation/holiday?

I’ve written more in-depth about how to start a conversation over here.

Now, let’s see how to avoid awkward silence as you continue the conversation.

pause

How to avoid awkward silence

Every time someone says something, we miss out on a lot of small details that can make or break a conversation. I will show how you can pick up on these pieces to keep a smooth conversation running.

1. Listen carefully to what the person is saying.

Say that someone is telling you

“We came back from Thailand a few weeks ago”

What pieces of information does that sentence actually contain?

2. Break down the sentence into the different pieces of information

(Don’t worry if this sounds technical, this will happen automatically for you as soon as you get the principle.)

He’s been in Thailand

He’s been there with others; “We”

He came back a few weeks ago

3. What questions could be based on these pieces of information?

    • How was Thailand?
    • Who was he traveling with?
    • How long was he there?
    • What did he think about it?
    • What did they do there?
    • Where in Thailand did he go?
  • How was the jet lag?

And so on… As you see, you can pull a lot of different threads out from each sentence.

4. Keep what the person is telling you in the back of your head.

Whenever the conversation runs dry, you can go back and ask questions about what you were previously talking about.

Click here to read more about how to avoid awkward silence.

EXAMPLE:

The other person just said something you don’t know how to build on, and awkward silence is about to occur:

STRANGER -[talk talk talk]….so that’s why I decided to go for a brown coat instead of a black one.

YOU – I see. Yeah the brown coat looks great I think.

STRANGER – Yeah, thanks!

If you don’t come up with anything here, simply go back to any previous thread in the conversation:

YOU – By the way, how long did you stay in Thailand?

Here you turned a potentially awkward silence into a natural progression of the conversation.

One of the most common reasons for awkward silence is trying to only continue the current thread. Being aware that you can jump around freely like this in the conversation and go back to previous subjects will help you avoid awkward silence.

storyteller

How to Use Storytelling to Connect with New Friends

We, humans, love stories. Scientists believe that we are hardwired to like them: In experiments, they discovered that our eyes dilate as soon as someone starts telling a story.

By simply saying “So, a few years ago I was on my way to…” or “Have I told you about that time I…?”, something powerful happens in peoples brains.

You can use storytelling to connect with people and be seen as more outgoing. People who are good at telling stories are often admired by others. Other studies show that stories also will make people feel closer to you by being able to relate to you.

And as time pass, you will have more and more stories in stock.

Recipe of how to successfully tell a good story

  1. It needs to relate to the situation. Memorize your good stories to over time build up a stock. Stories are timeless, a good story can and should be told several times as long as there’s a new audience.
  2. Talking about how good you put people off. Therefore, avoid stories where you come off as being the hero. Instead, stories that show vulnerability prove to work better.
  3. Put people into the relevant context. Explain the setting so that everyone gets the story. More about this in the example below.
  4. Talk about things that others can relate to. Adjust your stories after the audience.
  5. Every story needs to end with a punch. It can be a small punch, but it has to be something. We’ll look more at this at the example below as well.

It’s important to realize that people with a lot of stories don’t necessarily live more interesting lives, they just present their lives in an interesting way.

I have a friend who’s an awesome storyteller. When he starts telling a story, people give him their full attention. Sometimes when he shares his stories on Facebook they get well over 100 likes. While Facebook likes generally doesn’t say much, in this case they show that his stories work. The reason they work is that he follows the rules of storytelling.

Here’s a story that he told me recently:

So a few days ago I’m waking up to an important day with exams and meetings. I’m waking up stressed because the alarm clock had apparently already gone off.

I feel totally exhausted and prepare myself for the day, taking a shower and getting shaved. However, my tiredness just won’t let go and I’m actually throwing up a little on my way out from the bathroom.

I become afraid of what’s happening but I’m preparing breakfast and I’m getting dressed. I’m staring at the porridge but can’t eat and want to throw up again.

I’m taking my phone up to cancel my meetings and realize that it’s 1:30 AM.

Notice how this wasn’t meant to be the story of the year – it’s just a great example of a nice story to pull of in a suitable situation.

What I like about this story, in particular, is that it’s not an exceptional event; you’ve probably been through several similar things in your life. However, this guy succeeds in turning it into an interesting story.

Also, notice how you probably felt motivated to read that story more than anything else you’ve read in the guide so far – that’s how hardwired we are to like stories.

Pay attention to the following:

  • He doesn’t try to look like a hero. Instead, it tells the story of a struggle.
  • It ends with a punch. The punch is often the difference between awkward silence and laughter.
  • Notice the pattern. Relatable -> The Context -> The Struggle -> The Punch

Whenever he’s telling these stories, he gets everyone’s full attention. Through these stories, he makes people feel good and makes them want to be around him. Storytelling is why people see him as an outgoing person.

Click here to read more about how to tell a good story.

What do you think about this system? Have you noticed how conversations become more interesting when you find you have something in common? I’m interested in hearing your comments below!

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Comments (16)

  1. LA

    This is both very illuminating and useful information. I love to read your articles.
    The thing is I work as a dentist. I love to connect more with my patients and get to know them better. However, it is hard to work in someone’s mouth and let them talk at the same time. Do you have any tip?
    Thanks
    L

  2. M

    I work as a cashier. The problem is, how do I figure out what the person does to guess their interests? Should I just ask them what they do david?

    • David Morin

      Make an assumption just like we did in the exercise in the article. But if you’re talking with a customer, the conversation might be too short in its nature to actually make it deeper. It’s not very practical in that situation, I think this method is better for a longer 1-on-1 conversation where you are not customer-cashier.

      • M

        How do you make an assumption without previous knowledge? Just on how they look?

        • David Morin

          Looks, clothes, the area/place/city you see them in, accent, body language, age. There’s lots of information to make assumptions, of course, a lot of your assumptions will be wrong, but once you get started talking you will get more and more information to help guide you. You also get better at guessing correctly the more people you talk and practice with.

          • M

            Thanks for the response. I’ll try it out

  3. Jared

    I do this kind of stuff when talking to people all the time, making assumptions about their interests snd stuff… usually im dead on. This is like being a conversation samurai or something… whether or not it makes people like me, i cant really tell. I think the important thing is to just be real and unafraid of offending people, especially if you ever want to end up with sincere bonds with others.

  4. Camilla

    I am trying to connect with old friends this way (because when you grow up, you usualy change – so sometimes it feel like you don’t know each other anymore). But it’s hard when you sometimes think that the other person hold grudges against something. Is there a way to get past that? Like.. ..what can you say?

    I think also with my trauma that i forgotten memories that are really important to the other person.. (like, old internjokes) but i feel embaresed to tell that; that they need to refresh my memory. And the mode gets real awkward. Ideas?

    Omg, i just realice thats when i get back in my head and it gets silent. But I don’t think I’m comfortable to just tell the truth either..

    • Camilla

      Sorry for the novels.. 😁

      • David Morin

        Your comments and “novels” are always welcome here 🙂

    • David Morin

      It’s hard to say, it depends on if they actually seem to hold a grudge or if you are just afraid that they are?

      And about the other thing, I don’t think you need to be embarrassed that you forgot or don’t understand a joke. Everyone forgets stuff like that or they just don’t get it, many times people just pretend like they understand 😛

      • Camilla

        Good 😁

        Both I think. Both that I are afraid some of them are and that some of them acctually are. When you hit the wall you can’t be there for people like you should even if your physically there, because you’re mentaly finished and can be for a long time. So it’s kind of a trust you break “to be there”. I think. And it’s hard to get that trust back – some people maybe “moved on”. But who your stil connected to.

        • David Morin

          I think you can only do so much. You can only be yourself, be honest and kind. If they still hold a grudge against you it’s probably time to move on. Some people don’t want to understand.

  5. Mandy

    Great advice – thanks!

  6. Azeem

    Wow this is so realistic. I’m basically an introvert but this can get me a few friends. Thankyou David🙏

    • David Morin

      I hope so Azeem, glad you like it!