How to start a quality conversation with someone you don’t know


One of the hardest social situations to face is starting a conversation with someone you know very little about. You might already understand that the key to being a good conversationalist is to be a good listener; You need to ask questions that will get to the interesting part of someone, and then be truly interested in listening.

You don’t need to be extroverted to be a great conversationalist; you need to care about other people. You need to trust that you will find other people interesting because you are a curious, engaged person. The good news for introverts is that this means working a room doesn’t require comfort with crowds as much as it requires comfort with yourself.

The problem is that it’s hard to figure out how to get to that interesting part of someone. But here’s some encouragement: Forty percent of young people think they are shy, and the percentage gets higher over time. However most people do not have a shyness disorder to overcome, they just need a little more practice. For example, “Most socially confident people deliberately learn specific skills, like understanding the predictable format of a conversation with new people, and focusing on the topic rather than on how one is being perceived,” according to Erika Casriel, writing in Psychology Today.

So I found someone who is in this situation a lot, and actually gets paid for it: Moira Gunn, author of the book Welcome to Biotech Nation. Her radio show, Tech Nation, is known for introducing hard-core scientists to people who aren’t especially interested in science. She finds a lot of people to interview by going to the International Biotech Conference, and she does the interviews herself even though she knows very little about biotech.

The way that Gunn gets such fun and interesting interviews out of her subjects is by not having a preconception of what they’ll be talking about. She wants to find that spot where they are engaged and knowledgeable, because anyone on any topic will be interesting if they have that. She says the key is to be open to where the other person wants to go, and to listen.

It’s Gunn’s job to figure out a way to connect with these scientists and part of the fun of the interviews is hearing her do that, because it’s what we have to do all the time when we make small talk. Yes, the scientists are extremely smart, but Gunn says the hard part is to get them to the point where they are talking about something comprehensible.

“This is not about all the science someone needs to know. This is about what really connects with people,” says Gunn. “I have a rule. You get one strange word a segment.”

What’s an example? “Nucleotide.”

One of Gunn’s favorite interviews was with a food safety researcher who ended up talking about mussels. He told her that you are only supposed to eat them in months that have Rs in them, because in June, July and August the water is warm and bacteria levels go up, and muscles are basically filters.

Gunn’s favorite part of this interview wasn’t even the science. Mr Food Safety is a vegetarian. Gunn laughs out loud when she tells me. She is great at small talk because she can go to the International Biotech conference and find comedy.

Gunn has done interviews with difficult people for years, and by now she is able to get even the worst conversationalist into territory where he is interesting. But she’s had a lot of practice.

You have to practice making conversation if you want to be good. “Building confidence is like learning to swing a golf club. It boils down to knowing what the critical skills are and practicing them. Even Tiger Woods still practices for hours every day,” says Bernardo Carducci, director of Indiana University Southeast’s Shyness Research Institute (also in Psychology Today).

Of course, in order to practice this you have to open yourself up for some awkward situations. But there is no way to grow without being awkward at first, so try it. It feels good to be able to find the interesting thing about anyone you talk with. I find the more confident I am in my ability to do this, the more open I am to the whole world. After lots of practice I have a deep belief that everyone has something to offer if I can just get the guts to start the conversation.

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  1. Nina
    Nina says:

    Thanks for pointing out Gunn… I’ll tune in. Another person that has mastered the art of conversation: Terry Gross. On her NPR bio page she is quoted, "What puts someone on guard isn't necessarily the fear of being – €˜found out.' It sometimes is just the fear of being misunderstood." She’s the best!

    I just pulled out your book because I recall you talking about storytelling. You write, "Good talkers recognize that there's something interesting about every person and it's their job to get them talking. But you can't only bombard people with questions. You also need to reveal things about yourself. The best way is by telling fun and interesting stories that make you look good." Opening up is difficult and requires practice.

    I've never been the smartest, richest, or best looking person in the room, but I always received the job offer, closed the deal and got laid because the world rewards an authentic and engaging soul. Sure, sometimes it's easy to just fire away the questions, but good conversation is a bit like gay ballroom dancing – everyone gets a turn at leading and following.

  2. MarilynJean
    MarilynJean says:

    This advice is useful and very true. I am tagged as an extrovert, but often find myself clamming up when put in professional networking situations. Why? Because I already think that the people I will meet will be boring or disagreeable. By following the advice Penelope has laid out here, I find myself not only learning more, but enjoying the company of the people I am around. This of course means better networking, and in my personal professional case, better fundraising.

  3. Stacey
    Stacey says:

    This is a supplemental tip that I picked up from a magazine a long time ago: when people tell you a story, they don’t want you to respond with your own story. Whenever you tell a different story in response, what you are essentially telling the other person is that their experience is less relevant and less important. If you’re dealing with someone who’s already shy, then topping their story is only going to shut them down further.

    Good conversations, in my experience, typically resolve into a story-teller and an audience. If you feel unbearably shy, then focus on being a responsive audience. Be audibly impressed whenever possible and ask for explanations when conversation lulls. Don’t be afraid to politely disagree; a reasoned negative response also implies attentiveness. Good audiences are typically in short supply, so learning to be one will actually make you quite popular. Which is, I suppose, the whole point of Penelope’s post.

    (As one may suspect, I’m one of nature’s storytellers. Being a storyteller all the time will ultimately alienate people, even if you’re Ernest Hemmingway. If you’re a storyteller but feel disconnected, try learning to be an audience. I’ve found that deliberately being an audience is a lot more effective when trying connect with other people. It makes them feel important and meaningful to you; these are important emotions to elicit because people form friendships in order to feel validated. Just remember that people can tell when you aren’t really listening and people generally find that insulting.)

    * * * * * *
    This is a great tip. Thanks. I confess to be guilty of responding to a story with a story. And it makes total sense that this does not feel good to the first story teller. And, your comment makes me realize that playing storytelling battle games is not exactly the most engaging way to tell a story anyway.

    Thank you for making me a better listener and a better story teller– all in one comment!


  4. Catherine Jones
    Catherine Jones says:

    I’m a introvert. I naturally find myself listening a lot to what people have to say and, knowing that this is a good way to connect with people, trying to maximise it.

    But I find many people will monologue at me and I just get bored. Perhaps I haven’t mastered the art of finding what makes people tick but I’m wary that, given the chance, most people will drone on about themselves for as long as you will let them.

    Many people don’t ask you questions back and barely register your comments. Not sure if I’m doing something wrong or have the misfortune to run into lots of self absorbed people. Any tips of turning someone’s monologue into a conversation?

    • tara
      tara says:

      I have the same problem. Also, when i really look people in the eye and listen, I find they usually stop looking at me and forget to be interested in me too. Conversation bores me. It gets to the point where I will forcefully try to act a different way to see if I can manipulate the conversation. Its kind of like my life becomes an act…? if that makes sense.

  5. Joselle
    Joselle says:

    “Forty percent of young people think they are shy, and the percentage gets higher over time. However most people do not have a shyness disorder to overcome, they just need a little more practice.”

    I find that point very interesting. I almost always say to people, “I’m shy,” and then they give me a shocked look of disbelief. Several years back, I definitely had some serious social anxiety, so I’ll never be a natural social butterfly. But the older I get, the more I realize that, once the ball gets rolling with a simple statement or two, it’s very easy and natural for me to speak with all sorts of people. You do just have to have the guts, like you say, Penelope.

    Catherine Jones, my boyfriend and I talk about what you bring up a lot–monologues rather than conversations. My boyfriend is by far the most attuned, phenomenal listener I’ve ever met in my life. That’s what blew me away about him. From the he asked these great questions that showed his genuine interest and great attention to detail. It frustrates him that that often isn’t reciprocated. I think being a truly great listener is a rare quality. I have the tendency to tune out and ramble when I talk.

    I also have some people in my life who are truly self-absorbed. I think with them, you have to realize it isn’t so much about you. With those people, you may just have to jump in and get your comments in there. Also, in some families and cultures, you’re expected to interrupt in order to convey interest rather than just passively listen. Perhaps some of that plays into your encounters too.

  6. Chuck Westbrook
    Chuck Westbrook says:

    I always make an effort to be the guy who says hello to the new person in a group. I just remember what that feels like, and I know that most people would prefer to be approached rather than have to break in cold.

    That said, I don’t think it’s my natural gift or role–I just see that there’s a need to be friendly to those people and I do it. It feels at least a little awkward almost always, and I tend to get somewhat self-conscious. However, when I confess those feelings of awkward self-consciousness to my wife or friends, they often laugh at the notion that I am shy.

    Just because you are uncomfortable, doesn’t mean you shouldn’t reach out. Just because someone reaches out, doesn’t mean they are comfortable. It’s part of how many people are wired–we want to be accepted yet are afraid of conflict and rejection.

    * * * * * * * *

    Love this comment. It’s important to know that the people who look like they are the stellar conversationalists at the party are actually people who have conversation misgivings themselves. I really appreicate the image of the person who walks up to the new guy at the party is actually feeling nervous himself. So honeset, and inspiring — we should all be so kind as to appraoch the new person even though it feels awkward.


  7. Michelle Yan
    Michelle Yan says:

    Another post that hits the sweet spot! And not only do these ‘social awkwardnesses’ occur in networking but they have cropped up as campus guide, a new assigned mentor or chapter president. I agree that letting people know that you are genuine and care make a world of difference. Some small things such as a firm handshake and repeating someone’s name after they introduce themselves (Nice to meet you, Penelope.)indicate that.

    An interesting observation that cements the idea that EVERYONE is somewhat nervous- where does everyone go first? To get a drink so they can at least clutch at something.

  8. Michelle
    Michelle says:

    Here’s an interesting question this post raises: What happens when you’ve struck a good conversation with someone and they keep on rambling but you would like to meet other people? It’s obviously not a safe place for strangers to jump in and introduce themselves.

    Some tactful advice I’ve gotten is to spot a friend and say “Oh, have you met so-and-so?” and get another person involved a previously 2 person conversation. You can introduce people in this manner until there’s a decent group size and the conversation is flowing without your constant input. Then you can excuse yourself to talk to someone else or to fetch an appetizer (as an excuse:) without making them feel stranded. Not only can this free up yourself, but they will appreciate you assistance in helping them network!

    Any suggestions for doing so if you don’t know any other people in the room?

  9. Suze
    Suze says:

    GREAT post.

    And to the comment above re: responding to a story with a story — I’ve been guilty of that. And I agree, it’s not a great position to put the other person in. Not at all.

  10. Maureen Rogers
    Maureen Rogers says:

    Penelope – Like Chuck W., I’m a well-compensated introvert, uncomfortable at events where I don’t know anybody. Many of the professional events I attend are techie related, thus full of introverts. Like Chuck W., I will approach another loner to start a conversation, which I typically start by saying something about how much I hate things like this, how it’s so awkward to stand around when you don’t know anybody, etc. When I see someone sitting at a table by himself/herself, I’ll go over and ask if I can join them. (Nothng worse than sitting at that table for 10 by yourself.)

    Your post also reminded me of one of my favorite conversation stories. I was on a business trip that involved 6 hours of driving with a colleague I barely knew. On the way up, I asked him a few “starter questions” about where he grew up,and it was off to the races. He went off on a 3 hour monologue about his family, high school, ne’er do well brother, church growing up, first car, the street he lived on, his family’s house, the dog…. When he stopped for a breath, I would ask a follow-on question (“what color was the dog?”), and he’d be off again. On the way back, 3 more hours,this time about college,jobs,first car, second car, third car, wife, son, and political philosophy.

    What was riveting about “Jeff’s” monologue was how incredibly, stunningly boring it was, but I kept on asking him questions, feeling like I was on a bad date. (I’m old enough that dating advice to girls was all about drawing the boy out and hearing what he had to say.)

    He did not once ask me anything about myself. Not once.

    The upshot was that a day or so laterI saw him in the hall and said, “Hi, Jeff.” He looked at me without one iota of recognition.

    I still laugh when I think about it.

  11. Recruiting Animal
    Recruiting Animal says:

    This is always a great topic but someone who goes ot a conference to interview people as part of her job is not a perfect model of the average person.

    Let’s say you meet a stranger, find “the money topic” and he gives you all he’s got. How do you then get rid of him?

    When a reporter calls you she just says I’ve got to go and hangs up. And you accept it because it’s business.

    In a more informal setting, do you just hold out your hand whenever you feel like it and say nice to meet you and show him your back?

  12. Ivan Yong
    Ivan Yong says:

    I believe one of the most key element in making conversation is to start listening.

    You would be surprised how you can draw an introvert to tell you things so as long as you listen,

    In my experience as a Generation Y, who switch career from a Pharmaceutical Production Engineer which requires minimal socializing to a IT Solution Sales which is the direct opposite, listening skill wins me very meaningful conversation.

  13. Charity Mudzongo
    Charity Mudzongo says:

    I have also found that it is important not to pre-judge people before striking a conversation, I have often been left dumbfolded and amazed at how wrong I had been in my pre-judgement. People are not always what they seems….

  14. Charity Mudzongo
    Charity Mudzongo says:

    I have learnt never to pre-judge people negatively before striking a conversation because sometimes, they can actually see it through me and it affects the conversation altogether. Striking a conversation with someone unknown is almost like opening a package and not knowing what to expect inside until its opened….

  15. melanie gao
    melanie gao says:

    Charity I love your analogy – striking a conversation with someone unknown is like opening a package and not knowing what to expect. I will think of that next time I approach someone to start a conversation.

  16. jrandom42
    jrandom42 says:

    As an introverted adult Asperger, running through an open field with an entire regiment of the North Vietnamese Regular Army shooting a month’s worth of ammunition in 30 seconds at me, is far preferable to attempting to strike up a conversation with someone I don’t know.

    Guess I’m really screwed, aren’t I?

  17. Mark W.
    Mark W. says:

    Here’s the other side of the coin that can be even more challenging – a quality conversation with someone you’ve known for a long time. You know their likes and dislikes, interests, habits, etc. so well that finding a ‘new topic’ can be difficult. You ask what’s new in their life and then you go over what you’ve been doing lately. There’s times I can only go so far and then I’m drawing blanks as to what the next topic of discussion should be. If both people are experiencing this predicament at the same time, it really gets to be awkward. This other side of the coin challenge is to maintain a lively and interesting conversation. Sometimes and with some people it will take nearly no effort at all. However there are those times when I really have to work at it by truly listening and being engaged in the conversation. Maybe all that is required is to use the same skills as you would with someone you don’t know on someone you do know but in a different way or direction.

  18. Allan Bacon
    Allan Bacon says:

    I love meeting new people & am naturally curious, so this is something that comes easily to me.

    What works for me is finding areas of common interest. This is especially true when I meet new people (like on a flight, or on a business trip). I just keep asking questions about the topics that interest me.

    I think that “Everyone is cool” and that if you keep talking, you’ll get to what that cool thing is.

    Starting with “where are you from?” and going from there is great – I just think of everyone as an expert in something – and I just have to keep asking. So if they are from New York, I ask about some things that I saw there on a vacation. I ask anything i’ve ever wondered about NY.

    If they are an NFL ref (this happened one time), I ask about what happens when they blow a call, how do they get assigned to games, how do they get into refereeing.

    It’s always amazing what you’ll find out if you come from a place of curiousity. But you have to be willing to steer the conversation to the things that interest you.

  19. Mirce
    Mirce says:

    Nice said! I’m a kind of introverted..what introverted? I have social phobia to be precise and it is really difficult to make it in the current society.
    This condition happens mostly during the winter and on parties/trips. Otherwise, I can act normal!
    WHen I see how others manage to talk about something interesting my mind goes like a new CD. Then I spend hours thinking about that I can not put 2 words together :)
    What can be done in this situation?

  20. Sales Engineer
    Sales Engineer says:

    For those who don’t yet know and use them, the best words to develop a conversation are ‘How’ and ‘What’. They begin open questions and lead to informative answers. If you add some insightful comments, it doesn’t take long for rapport to develop.

    One caution, you may find yourself to a long monologue and you will need some more linguistic tools to deal with this if you have an ‘agenda’ of your own.

  21. maysam
    maysam says:

    i realized tht um not a good communicator with my x..he was always angry cuz i dunn talk a lot.otherwise my freinds enjoy my company they say that am funny nd intresting..when it refers to guys i cant be comfortable,i have a date after 2 days with a very hot guy he is my boss he works in the feild of modeling,he is showing intrest bt i dunn knw if he knws me more this will grow,or by silence nd insuitable words its gunna work good.

  22. Houston
    Houston says:

    I tested this out my self, body control is a significant factor in relation to an excellent conversation. Keeping your facial expressions relevant to the story being told is critical, As well as sitting/standing up straight while listening or talking. Plus Does anybody want someone just stareing at them with big old eyes the whole time theyre talking? No, follow the “storys” emotions and show that on your face by either smiling,lifting your eyebrows,or giving them the old “wow thats crazy” is allways good. question for you guys though, how do you get to talk with a crowd of people more comfortably?

  23. Fuzzy Soul Tiger
    Fuzzy Soul Tiger says:

    what’s awkward for me is that, as a child, there’s so much freedom and innocence to seemingly make friends with the whole wide world. the more you grow up and learn more boundaries & rules for socializing, I now often feel like I have to be re-educated on how to make the simplest of connection…ESPECIALLY because everything I enjoy doing (writing books, making fun videos, singing and acting) are all activities that require getting out there and relying on new faces all the time to make a name for yourself.

    you wrote a great piece and though you look at videos thinking, “this guy doesn’t need any help”, I still feel some anxiety about what the right approach is. – Fuzzy Soul Tiger, Mr. PJ

  24. Donna
    Donna says:

    I experience people mostly brag about there grandchildren or the education (college) there kids are getting. Our children did not go to college or did we & we also don’t have any grandchildren, so this makes me very uncomfortable & uneducated. How do I respond to this.

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  27. For Kids Free
    For Kids Free says:

    Good conversations, in my experience, typically resolve into a story-teller and an audience. If you feel unbearably shy, then focus on being a responsive audience.

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  29. friv
    friv says:

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  30. JT
    JT says:

    Having good, confident conversations is one of the building blocks to becoming more outgoing–and in turn more confident in general.  I work with guys who have a hard time talking to women, and this is something they really struggle with.  I know you weren’t writing with that segment in mind, but the info you have is really interesting and I’m going to incorporate some of the principles in my daily work.  I’m starting a series of posts about becoming outgoing/confidence building on my blog at, and hope it will help people get out of the rut they find themselves in.  Thank you for the great information.  JT

  31. Okeefe Lily98
    Okeefe Lily98 says:

    I feel comfortable with starting a conversation with a question.
    But I don’t really know how, especially if it is with someone I don’t know well at all.
    Any sugestions?

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