How to Chat Someone Up 101 (for Introverts)

Many introverts today are accepting positive self images for themselves. After all, introversion is a legitimate personality style. We are learning not to try and be like someone else but to make the most of who we are. Famous introverts like Sir Isaac Newton, Mother Theresa, Jackie Kennedy, Albert Einstein and Michael Jackson give us great examples and even more permission to be who we are and win. As I explain to my clients around the world, “If you try to be like someone else, the best you can be is a poor imitation. Instead, try to find out who you are and be the best YOU that you can be!” This is the winning way.

We can be inspired by the great introverts who have gone before and we can learn some of their coping techniques but it’s up to us to be ourselves.

Recently an introvert sent me this email. “Sometimes I need to be social, we all do, and I'd like to know how I can get right into it at will (okay, that's wishful thinking, it'll never be that easy). I was wondering if spending most of my time alone is the only way to hone my social skills…. Thanks for any help you can give me. Patrick”

I’ve been getting a lot of email lately from introverts who feel the same way as Patrick. They understand it’s important to spend time alone (introverts need to spend up to half their time alone to be really happy) but the introverts who write me still want to know, “How can I chat someone up when I need to?”

One thing I’ve noticed in the few articles I’ve read on the internet about networking and socializing for introverts is that these articles just aren’t specific enough. They give good general advice, but it’s things we’ve heard all our lives and still don’t “get”, such as “show an interest in other people”, “get out more”, “take the spotlight off yourself and put it on the other person.”

I’m going to give you some specific things to say to get the ball rolling.

As you practice, start small. Try one thing at a time. Don’t get discouraged if you flop. Keep trying and pretty soon, you’ll (OUCH) be the life of the party! No, no no. We are not going to live here. We are just going to be a good visitor.

My tips today are about the social context of business. If it’s the social aspect of dating you’re wondering about, I have a great eBook on dating tips called “Dating Tips for Introverts” that you can pick it up at my website. It’s introvert-specific information you won’t find anywhere else.

In a business context, first let’s deal with this whole concept of small talk. Unlike us, extroverts actually enjoy small talk and 75% of the people you meet are likely to be extroverts. The suggestions I give may seem crude to you and they are very superficial, but this is the nature of small talk.

Small talk has to be “small” enough that no one is antagonized. It is geared to include as many people as possible, excluding as few as possible. The general rules are to avoid topics such as politics and religion and to focus instead on matters so innocuous that no one can’t join in.

Next, please realize that you – disliking to talk – are the perfect audience for extroverts. They like being asked questions and enjoy talking while someone else nods with interest or chimes in occasionally. This may sound strange to you but it’s true.

In some cases people will wind up thinking you’re a fascinating person because in your presence they hear themselves say fascinating things. This is the magic of relating. Amazing, isn’t it?

My grandmother used to be active in bringing legitimate Broadway theater to Chicago, the “Second City”. She held banquets to host famous actors and actresses. Before an important dinner, she’d research their lives in the library (no computers back then) so she could have what she called some “intelligent conversation” with them over dinner.

Here are some sample questions she might have come up with, “Few people probably know that you grew up in India, but I find that fascinating. How did it happen you were born there?” or "I understand your first real break was in playing such-and-such a role in Such-and-Such a play. Wasn’t that a little out of character for you?” or “What’s it like to travel so much and raise children?”

My grandmother prepared ahead of time because she knew who she’d be talking to and you can do this, too. As well as lightly researching the companies, backgrounds, schools, and interests of people who are likely to be at the meeting, try to have a short supply of ready topics on hand that are general in nature. Remember, because it’s small talk, it can’t be something controversial or very “heavy”. Avoid topics like immigration, terrorism, SARs and mad cow disease. Instead choose things of local or personal interest. Perhaps this is why “Great weather we’re having, isn’t it?” is the be-all and end-all of small talk. It’s safe. It’s obvious and it’s readily available.

At the time this article is being written, people are interested in landing on Mars. The gophers are pretty thick where I live right now and no one really knows why. Pick loose ended topics that people aren’t very emotional about.

This is an interview style familiar to you if you watch the great interviewers on tv or hear them on radio. Top interviewers prepare their questions carefully ahead of time so it’s ok for you to do that, too. And pretty soon you can throw away the notes!

Here's a list of questions you can ask any extrovert that they will probably enjoy answering.

(1)“What's new?”

It’s hard to realize that this is a legitimate way to start a conversation but it usually works if said with enthusiasm and expectation. Or you might try, “What’s new? I haven’t seen you for awhile …. prompting them to continue with raised eyebrows of expectation!”

(2) Let something on the person catch your eye – this works especially well for intuitives (the ENs or Ins in personality typing) - and comment like this … “Where'd you get that [gorgeous leather purse][totally unique green hat][efficient looking daytimer][antique desk], [adorable Vintage costume]? It looks so cool!”

Say this with enthusiasm not earnestness. You don’t really want to know but you want someone to talk to you tonight!

(2)Here’s another one … “Boy the traffic was really something on the way over here! Did you have trouble getting here on time, too?”

They can go either way with this and it may also lead to a discussion of cars, policemen, intersections, routes, the way the town is {growing][shrinking], etc.

(3)If you’re at a meeting and I hope you’re at several of these a month as they’re the easiest ways to meet people and network … “Great speaker, wasn't it? Do you like public speaking?” or “That guy was pretty interesting. Wonder who got him for the speaker. Ever heard of him before?” or “What’d you think of the speaker?” [can go either way]

Then just listen. Hopefully there will be some dramatic reaction or colorful stories you can enjoy hearing about.

(4)“How about the X’s [name a professional ball team] game last week? That was really something!”

This conversation can go either way. Remember to keep it to small talk, so mostly you want to keep the person talking rather than really exchanging significant information or taking the topic somewhere that it could get antagonistic.

(5)Also at the meeting … “This is a really nice [setting] [restaurant] [dining room] [campus] [car], isn't it?

Very interesting decor.” With any luck at all, they will have a strong opinion, some experience in other places that were [better][worse] and you can listen.

These are questions your extroverted associates should enjoy talking about. If you listen actively when they reply, you can get them to carry the conversation for awhile as they warm to the topic.

To extend conversations like this so you don’t have to go somewhere else and start all over, try peppering your listening with what are calling “flavoring” words and phrases. These are verbal cues for the person to continue talking. They are said in an inviting tone of voice. We are inviting the person to continue by showing interest.

“Really? Tell me more.”
“Where’d you learn that?”
“Where’d you hear that?”
”Where’d you find that out?”
“Where can I find something like that?”
“It must have taken a lot of time to find that out.”
”You’re really good at this, aren’t you?”

Of course if the person you’re talking to is an introvert, you’ll want to keep it short and move on since both of you dislike small talk.

Once we get the idea of what small talk is, we can join in as well as everyone else. Remember the general rule is to keep the topic so “small” or open-ended that nobody feels left out or antagonized. Save your
”big” talk, your serious conversations, for your introverted honey back home in front of the fire.