How to Have and Hold Dazzling Conversation With Anyone: We Review 11 Science Backed Steps

Do you know how to have a conversation? I don’t just mean any old boring conversation, I mean do you know how to have dazzling, memorable, incredible conversation? 

Knowing how to start, hold and end a conversation smoothly is one of the most important people skills you can have.

The art of sparkling conversation is one of our most requested topics at the Science of People. So a few months ago, I decided to do a bit of research on the topic to write this master conversation guide for you.

What makes a bad conversation awkward and a good conversation amazing? 

I noticed a pattern—most of the bad conversations had a very specific sequence of events leading up to the actual awkward moment. Here’s what we heard over and over again:

• I signed up for this networking event a few weeks before and had no idea who was going or what the organization was all about, but a friend of a friend recommended it.
• On the way over, I caught up on a few calls and checked my email before walking in.
• My calendar said 5pm start time, so I showed up at 5:30pm hoping I would be fashionably late.
• Once I got inside, I noticed the event was much larger (or smaller) than I anticipated and, oops, someone was presenting up front. I tried to get my name-tag and sign in as quietly as possible.
• I missed most of what the speaker said, but when she finally finished up people around me began to rekindle conversations and talk about what was said.
• I tried to talk to a few groups around me, but couldn’t really engage or had a bland back and forth.
• Most of the night was awkward and not helpful—I didn’t make any useful connections.

I want to stop this pattern! How can you make dazzling conversation with anyone you meet? How can you get business and connections and dates out of your meetings? I want to show you that there is both an art and a science to effective communication.

I have broken down the structure of a conversation into 11 steps that will take your average interactions and make them awesome ones.

The Step-By-Step Guide to Having Awesome Conversations:

Step #1: Conversational Intention Gives You Purpose

One of the biggest conversational mistakes is going into your events, dates, meetings and parties directionless.

You would never start driving to a new destination without the address so why would you start a conversation without a goal in mind?

A conversation without a game plan is like driving without a map.

Like any good athlete, conversationalists practice, prepare and execute with the intention to win. While you don’t want to ‘win’ a conversation, you might want to win business, win friends or win new ideas.

Before any social interaction, set your intention, know your crowd and do your research. This doesn’t have to be anything major. Just think of one sentence answers to the following while you get ready or are driving to your event: Who, What, When, Why.

• Who: Who is hosting the event?
• What: What kinds of people are going?
• When: When is it and what’s the schedule?
• Why: Why are you going?

Even a simple, “I want to find some new clients” or “I want to have a great time” sets up an intention that means you are more likely to have purpose while speaking to people. Purpose provides confidence, boosts influence and is contagious. As humans, we like someone with direction.

Want to truly make every conversation count? Never have an awkward silence or boring conversation again. Discover the ultimate course to mastering your self-improvement without losing your authenticity.

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Step #2: Approach As Friend Not Foe

We make our first impression in the first few seconds of seeing someone—this happens sometimes before you even start talking. Most people think that we don’t make our first impression until we start talking, but this is not the case. Be sure that before you even start the conversation, you are approaching it with open and confident body language. When we first see someone, our brain is trying to gauge if they are friend or foe. You want to signal ‘friend’ signals right off the bat. Here’s how to have open body language right when you walk in the door:

• Keep your hands visible
• Roll your shoulders down and back so they are nice and relaxed
• Smile when you see someone you recognize or you want to talk to
• Make eye contact as you walk towards them or say hello

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Step #3: Jerry Seinfeld’s Conversation Hack

Have you ever watched Comedians in Cars Getting Coffee? (Best. Sunday. Morning. Treat. Ever!)

Jerry Seinfeld gave an amazing social tip to make small talk whenever he meets strangers. And this tip ALWAYS works, because there will ALWAYS be an answer from the other person.

What is this tip? Watch the video below to find out:

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Step #4: Use Conversation Openers

What is the best conversation opener you have ever heard?

What is your go-to conversation starter?

The hardest part of a conversation is the opener. We tend to agonize over who and how to approach someone for a conversation. But don’t worry! A few conversation starters are the easiest way to get the chit chat ball rolling.

• First, research has found that the most effective conversation starter is a simple, “Hello, how are you?” It’s super easy, but it works!
• Second, you can always use context to help. Ask how the wine is or comment on the venue or event. These are extremely subtle and make it easy to strike up conversation.
• Third, we have 57 killer conversation starters you can use in almost any situation. Keep them in your back pocket.

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Step #5: Bookmarking

Some of the most talented conversationalists do something called ‘Bookmarking’ during conversations. This is an advanced technique that I love, but it does take some practice. The bookmarking technique is when you add markers or emphasis to a certain part of the conversation that can create a deeper connection. Bookmarks are verbal markers you say to make it easier to follow-up or have something to talk about in the future. Here are the different types:

• Future Mentions: Let’s say you are talking about conferences and someone mentions they are going to the same one as you in a few months. If you like the person, you can ‘bookmark’ it by saying something like, “I’m headed there as well, we should get coffee after one of the sessions.” This is a bookmark that you can follow up on later.
• Inside Jokes: These are my favorite—they are very rare but are lovely when they happen. Let’s say you are chatting with someone and something interesting or funny happens. You can create a bookmark and then mention it to repeat the laugh again later. I also call this ‘Milking the Joke.’ For example, I was on a long cross country flight where they gave everyone a little bowl of nuts before take-off. For some reason they put the bowl down in front of us and then took them away not even a minute later because they had to ‘clean-up.’ I literally had time to eat one nut out of the whole bowl. So when they took it away, I turned to the guy next to me and said, “Budget cuts and recycling are really killing the experience.” And he laughed and I laughed and we struck up a conversation. During dinner, we both made a joke about having to eat fast in case they took it away. Whenever they served us coffee we giggled about hiding the mug just in case they had to ‘clean it up.’ I gave him my card and he followed up with an email with the subject: “Don’t take my nuts!” and said I should give him a call next time I was in Dallas for a free dinner at the steakhouse he owned—free steak! I credit milking the joke for this free meal.
• Same Same: Sometimes you can verbalize a ‘same-same’ moment. A same-same moment is when you both find out you have a similar interest, background or commonality. You bookmark it by exclaiming how crazy it is you have that in common. For example, I met a woman at a party and it came out that we both are the eldest of three sisters and have a 12 year age span between us. I bookmarked it by exclaiming, “WOW! I don’t think I have ever met someone with the same family situation as me—I’ll have to Facebook you next time one my sisters asks me to get her out of trouble, because you might be the only person in the world who gets it.” She agreed and we shared multiple stories of this occurring. We became Facebook friends and sure enough, she sent me a screenshot of a text from her sister requesting a ride.
• You Have to See: Sometimes you can bookmark with a follow-up mention. I often bring up books, videos or articles I like to people while speaking to them. If they give me an eyebrow raise and seem interested I will bookmark it by saying, “I’ll be sure to Tweet you the link so you can check it out!” I love doing this because I get to share something I like and they will often send recommendations back to me.

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Step #6: Find Sparks

Once you have the conversation started you want to keep it going. The most charismatic people look for conversation sparks. They bring up topics, look for ideas and ask questions that spark energy or get the person excited. If you orient your questions and intention around eliciting sparks, it will be much easier to keep the conversation going and avoid awkward lulls or directionless chit chat. 

Sparks usually come from asking someone about topics that trigger dopamine. This is a chemical that makes us feel excited and engaged. I recommend triggering dopamine by bringing up topics that will help someone feel joy. Here are my favorite sparking questions:

• Have any big vacation plans coming up?
• Working on anything exciting recently?
• What’s the best part of your week?
• Tried any new restaurants lately?
• Working on any personal passion projects at the moment?

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Step #7: The Secret is in the Eyebrows

I want to teach you one of the easiest and most fun nonverbal conversation tricks. The eyebrow raise. Across cultures, the eyebrow raise is what we do when we hear or see something interesting. When you see someone do it in conversation it often means you have said something engaging or brought up a topic that peaks their curiosity. The eyebrow raise is the physical indicator of a spark. It clues you in to a topic that they might like discussing.

I had a great example of the eyebrow raise happen to me the other day. I was sharing a story at a networking event with a marketing executive. I was telling him about a great commercial I saw while watching a Portland Timbers game (the Portland soccer team). He was nodding along while I talked about the commercial, but when I mentioned it was during a Timbers game, his eyebrows did a nice jump. After I finished the story, I asked him if he was a soccer fan. Sure enough, he said his son was trying out to go pro—and this started a great conversation about soccer, sports and kids. We traded cards and I hope to do a workshop for his marketing team.

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Step #8: Captivate with Stories

I listen to a A LOT of podcasts. One of my favorites is the Tim Ferriss podcast. He interviews the most fascinating people and asks really interesting deep diving questions. On one of his podcasts with Jimmy Chin, a professional climber, Jimmy was talking about advice he would give to first time climbers. This was interesting, but then he started telling a story to back up his advice about one of his first climbs. As soon as he started the story I was sucked into it. I leaned in, gasped at the surprises and held my breath for the ending. Not only did the story mentally capture me, I also felt a physiological response while he told it. I will remember his advice far more from the story than from his tips even though the story was not as direct.

• What are your favorite stories to tell?
• What is a story you can tell to back up a claim?
• How can you answer in anecdotes?

Warning: Stories are great, but don’t be a conversational narcissist—make sure you do equal talking and listening by asking for their stories as well.

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Step #9: Encourage Reciprocity

No matter how great your body language is or how many funny stories you tell, if you commit a conversational sin you will turn people off. The biggest deal breaker is ‘Conversational Mooching.’

You know when you ask someone a question and they answer, but don’t ask you back? You ask them where they are from and they say “New York”.. and then silence.

We expect reciprocity in conversations.

When we share something, we want someone else to share something. When we ask a question we want them to answer and ask us back. It doesn’t have to be tit for tat, but we are coded to look for and be treated with equality. Be sure you are not a moocher and give back as much as you get.

My three favorite words? Not “I love you” — although those are good too! Always ask people, “How about you?” after you finish answering. These three little words are perfect for encouraging reciprocity.

• Special Note: One other conversational sin is being a one-upper. A one-upper is someone who constantly has to outdo you or your story. You had a bad day—well they had an even worse one! You traveled to 20 countries—well they traveled to 25 AND have done all 50 states! Let people enjoy their moment and celebrate with them, don’t one-up them.

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Step #10: Exits

You’ve started a conversation, sparked stories and gotten to know each other—now you have to end it. Sometimes the art of the last impression is just as hard as nailing the first impression. The art of ending a conversation is easy. I have an entire post on the art of a lasting impression, but I encourage you to use bookmarks to end well.

• Future Mentions: “Well, I can’t wait to see you at that ___ coming up—I’ll email you!”
• Inside Jokes: “It was great laughing with you. I’ll be sure to ___ in the future ;)”
• Same Same: “I’m so glad I met a fellow ___ fan. You made my night!”
• You Have to See: “I’ll be sure to send that link your way, great talking to you!”

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Step #11: The Post-Mortem

I know after an event or date you can be tired and all you want to do is flip on some Netflix and call it a night. But, take a few minutes to do a post-mortem. This can be in your head as you drive home, talking with a spouse or roommate or writing in a journal. Answer the following three questions:

• What went well tonight?
• What did I learn?
• Who should I follow-up with?

The art of conversation is a skill—you have to keep learning and honing your ability. Your post-mortems can help you identify patterns and remember to follow up on bookmarks, LinkedIn connections and promises.