10 Ways to Be a Better Conversationalist

20 June 2019 | 17 Comments

I often find myself in situations–both online and offline, often related to my business–that require something that introverts like me dread: small talk. To me, small talk feels like filling time instead of actually making a connection with someone.

Over the years I’ve tried to learn how to turn small talk into something more substantial. I’ve found this to be helpful both personally and professionally, as a huge part of my job is about meaningful connections.

Today I thought I’d share some of these techniques with you. A lot of them are built around questions I’ve learned to ask that open up a conversation instead of stifle it, but I’ve also found that it’s important to share parts of myself in conversations too (as an introvert, I have to actively do that sometimes instead of just deflecting).

  1. Many conversations with strangers start with the same basic facts. I try to get beyond them quickly to the interesting stuff. What do you do? Boring basic necessity. Do you like it? Why or why not? Interesting.
  2. When someone asks where I’m from, giving a one-word answer makes things harder for both of us. Having a few basic stories reinforced with opinions makes things easier. For example: “I grew up in Virginia and moved to St. Louis for college, and I liked it so much better here that I’ve stuck around here ever since.”
  3. If someone says, “I’m a fan of your [game/product/company],” I thank them, try to give them an opportunity to talk about what they specifically like, and maybe share an insider story about it if they seem interested.
  4. I generally avoid the “do you know X person” line of conversation, as it typically leads to a dead end (either a yes or a no).
  5. Ask people about extreme events—the worst and best of situations. They stick in our memories and are easy to recall. Worst date, best trip, best Halloween costume, etc. Instead of putting someone on the spot by asking for their favorite X, which can cause a lull while they think it over, ask for “one of the best things about X” or “one of their favorites. ”
  6. Strive to make connections between other people, possibly even in a way that invokes a reaction (e.g., “Tom, I think Sally enjoys graphic novels even more than you do!”)
  7. Steer group conversations towards inclusive topics. Either avoid inside/private jokes or provide context for them so everyone is in on the joke or story.
  8. Ask for advice, suggestions, and recommendations. Not only may you learn something important, but people love to offer advice.
  9. Always enter social situations with an answer to “What have you been up to lately?” Also, instead of asking that question, help the person with more constraints (e.g., “What did you do this past weekend?” or even more specific: “Did you try out any new restaurants this past weekend?”)
  10. A few general categories of topics you can turn to when needed are firsts, routines, pets, injuries, and origin stories (e.g., “How did you get involved with that?”).

This is just a starting point, and I’d love to hear your tips about conversations in the comments.

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17 Comments on “10 Ways to Be a Better Conversationalist

  1. A great, unusual tip I got from a beloved pal: when you meets someone, imagine they’re a long lost friend, with whom you’re reuniting after a long absence, but they have amnesia so they’ve forgotten.

    I don’t know if this will work for everyone, but it works wonders for me.

    1. Nick, I love the amnesia twist. With a little imagination, one could nudge the other person’s self-concept—hopefully in a positive direction! And the fun of doing that might even nudge the introvert in oneself outward.

  2. Another opportunity to learn. It’s always difficult when some says they love my games or what NIBCARD Games do.

    Most times, the introvert in me takes over. Great to learn I could open up the conversation a bit more with ‘oh…thank you. What do you like about it/them?’ and even give an inside story about the origin.

  3. Another tip from an introvert is to actively listen. I find that I sometimes am so worried how to reply that miss what someone is saying. Best to listen with all your attention and then form your answer. I have gotten better over the years but I still have to practice it.

  4. These are great tips. Sometimes when it’s a group of introverts talking, calling attention to it can be an ice breaker. Once I was in a circle of strangers trying to make connections at a game design meetup and one person said “we did it guys! We started a cool small talk circle!” and everyone relaxed.

  5. I don’t struggle talking with new people very much. I love meeting new people and I enjoy their stories and histories. People are infinitely interesting and wholly unique, if you keep that in mind there isn’t anything to dread. Meeting new people always guarantees something new. Both parties benefit from new connections and everyone is lifted, even if it doesn’t go well. No tips or strategies, just how I am.

  6. Great tips Jamie. For myself, and perhaps others, I often have to keep in mind that many other people are not as analytical as myself. I suspect that many game designers are similarly wired this way. To me, this means that most people are simply looking for a superficial interaction that is fun and lighthearted. I feel this is unfortunate because so many of us make very interesting decisions that I think are worthy of deeper analysis or reflection. Some have told me that this comes across as being pedantic. Therefore, most of the time I keep my interests to myself unless the person I am talking to seems interested in a deeper discussion.

    One thing I am testing out now is called the “insight game” where I ask people to share an interesting Insight they have observed in the world. This is open-ended and can apply to anything. Thus, this allows the participant to take the conversation where they want to go. It also allows the participant to build on something that they know quite a bit.

    For example, I drive to work and have frequently bein irritated by other drivers techniques. Up here in Toronto Ontario Canada there are no rules that specifically state that you must only pass vehicles on there left. Therefore, quite often people in expensive cars tend to leave the normal lanes of traffic and move into rightmost lanes that are intended for on ramp drivers to merge into the main flow of traffic. And so you might say, what is the big deal? Everyone is going in the same direction and no one wants to have lane police.

    But here is what I have observed that I think is interesting. As more and more people shift over to the right-most Lane and get ahead of others the next thing that happens is that when they get to the end of the merge lane they force their way back into the traffic. This creates an interesting feedback loop that causes this next Lane to move more slowly and therefore encourages more people to shift to the right. As traffic gets worse and more people start shifting over to the right on ramp lane the main flow right lane eventually grinds to a halt. This causes further congestion for everyone else and leads I think to gridlock.

    Now everyone discuss. :)

    My hope is that if we get people to share their insights from their perspective this will make most social conversations very interesting and compelling. And, this adds a level of gameification to the social interaction, which of course I find amusing and fun. Perhaps this might catch on. Or better still, hopefully someone will take this and make it better.

    1. I think perhaps the lane that is getting merged into slows down to let the merging cars in but I’ve read that if everyone used the technique known as “zippering” it would actually be better for traffic overall!

  7. I have a friend who, when he is introduced to someone, asks the new acquaintance, “How do you two know each other?” Even if he gets a one-word answer, it opens up the conversation

  8. I see this all of the time…I work in a sector of the government which attracts highly intelligent introverts and of course my favorite hobby and industry attracts, generally, the same type of folks. As an extrovert, I feel a sense of responsibility to carry more than my share of any conversations. All of your tips are spot-on from a extrovert’s perspective, as well!

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