20 Ways to Start a Conversation and Build Into a Connection

I’m an introvert. Let there be no doubt about it.

I often feel innerly awkward around people I don’t know, and I tend to clam up and not speak. At times, I even do this around people I do know.

Yet, I also know how incredibly valuable human relationships can be. Close friends and close family relationships add a ton of value to life. They’re constantly there for you at every stage in your life, providing the help you need when the chips are down and providing a real boost to you when things are going well.

Beyond that, there’s incredible value in the weaker links as well. They’re often very useful to tap for advice when you need it and can often open doors in your career and life that you might never expect.

Crossing that barrier from being nervously awkward around someone I barely know to having a new friend (or at least a new person to associate with) seems like a gigantic leap for me at times. I know that many introverted people feel exactly the same way.

Yet, over time, I’ve built up a lot of little tricks to help me past this. Because of that, not only do I have a small group of close friends, I also have a very wide network of other friends, people I know from the area, professional peers, and other folks, many of whom scarcely recognize how introverted I actually am.

I don’t view these things as some kind of “act.” I view them as tools that help me to click with others in a way that I never could without them. It opens the door to relationships that my own introverted nature would have killed at the start.

Here are twenty techniques I often use to start a conversation or build upon it.

1. Be comfortable. And clean.
You are far better overdressing or underdressing the situation a bit and feeling comfortable in what you’re wearing than dressing “perfect” and feeling out of whack. Another vital tip: never go into public without having bathed in the last 24 hours and without having cleaned your mouth in the last several hours. You don’t want people to remember you for the smell.

2. Have a current event on your tongue.
Whenever I go anywhere, I make sure to at least load up CNN or another news site and check out any breaking news. Breaking news is almost always an incredibly easy conversation starter, particularly if you have a bit of knowledge about what’s going on. Even in the era of cell phones with web access, the personal sharing of events makes a big difference.

3. Ask about them. Always.
People always love to talk about themselves. It’s something they know about and something they’re often happy to discuss because it means, on some level, you’re interested in them. If you’re ever stuck with nothing to say yet want to continue the conversation, ask the other person something about themselves. This is why you’ll often hear people asking others about their careers, their hobbies, the weather, the score of the big game, and so on. Often, it’s not so much a burning interest on behalf of the questioner, but a way to get the other person to talk.

4. Listen.
When someone is talking, don’t stand there trying to think of the next thing you’re going to say. That doesn’t build a relationship. Instead, listen to what they’re saying with as much care as you possibly can. Most people, when they’re talking about themselves, give you tons of different avenues through which to continue the conversation, either by asking them more about themselves or to follow up.

5. Touch on elements of rapport.
While you’re listening, try to identify elements that you have in common with the person speaking. Then, during a breath in the conversation, mention that element that you have in common. This gives the two of you a touchstone, something that’s a key part of the foundation of any relationship. I’ve used something as mundane as shopping at the same grocery store as a touchstone in the past.

6. If you’re unsure how to follow up, use their last few words.
Just simply repeat the last three to five words they said in an uncertain voice, as though you were asking a question. This will almost always encourage the person to continue along on their train of thought, giving you further room to listen and find elements of rapport.

7. Have a repertoire.
One thing I do to practice my conversational skills is to work on and expand my repertoire of entertaining stories. When you’re relating an experience you’ve had to someone, it’s really a matter of how you tell it that makes it boring or really interesting. I try to have a collection of worthwhile stories and I sometimes will practice telling them, looking for ways to spice them up. I try using different voice inflections, raising and lowering my voice along with the story. I’ll practice doing these types of things in the shower, for example, and I’ve found that the more I practice them, the easier it is to just tell a story in public and make it interesting enough that people will want to listen to it. Interestingly, another great way to practice your storytelling ability is to read children’s books aloud to children. In order to keep them interested, you have to exaggerate your voice inflections, which you can then do in a more muted way as a great conversation tool.

8. Remember who people are.
This is something that’s particularly tricky for me. I’m good with names (I can remember the names of many of my son’s friends and some things about them), but I’m terrible with faces. I’ll see someone’s face and I often have a difficult time recalling that person’s name. My solution for this is to simply practice. Whenever I see a face I think I should know, I give them a good look and run through what I know about them in my head. Do it enough and it becomes natural, plus you’ll feel your memory gently expanding, too. The best part is that you’re able to pull out such information during the second or third conversation you have with a person, which is a fantastic way to begin to cement a bond.

9. Don’t feel bad if people don’t remember you. Remind them without expectation.
I usually expect that people don’t remember me, so I often remind people that I’ve not met often by introducing myself again while also mentioning what we have in common. This is often a very helpful refresher for the other person and it leaves them much more likely to carry up their end of the conversation with you.

10. Never eat alone.
Yes, this is the name of the Keith Ferrazzi book that I quite like, but it’s also a truism. A meal is an inherently social occasion and, if at all possible, you should make it such. Eat breakfast with a co-worker. Eat lunch with a friend or a professional peer or with your mentor. Eat dinner with your family or a close personal friend. Not only are meals a great opportunity for you to be forced to sit down and interact with others, they’re also good conversation starters in themselves.

11. Talk less.
I tend to find that I overcompensate for my nervousness in social situations by rambling. I’ll start talking about something and the words keep flowing because I’m nervous. You should never fill empty space in a conversation with your words. That’s the surest way to bore and drive away another person. Instead, ask a question and encourage the other person to fill the conversation space.

12. Have conversation goals…
What’s your purpose for talking to this person? It’s always helpful to have some sort of objective in mind for the conversation, whether it’s just to build a better bond with this person, to get specific information, or something else. Know why you’re talk ing to this person and what you hope to achieve in the conversation.

13. … but don’t follow those conversation goals doggedly.
Of course, if you chase your goal like a dog with a bone, you’re likely to drive the other person away. I usually look at it this way: the goal of almost any conversation I have is to bond better with this person. The secondary goal is to obtain that piece of information I want or whatever else I wish to get from that conversation. If I recognize that my primary goal in almost every conversation is to just build a stronger bond, then it’s much easier to not be dogged with my secondary goal for the conversation.

14. Ask questions that flatter, yet take people off their game.
This is probably the most difficult tip, but I consistently find it useful. When I know someone a bit and there’s a lull in the conversation, I’ll ask them something like, “What’s the most exciting thing going on in your life right now?” Or, maybe, I’ll ask, “Where do you see yourself in five years?” I do this because it opens the doors to people’s hopes and dreams and aspirations, things that are personal (but not too personal) yet also fill them with good feelings when they talk about them, and things that make the other person feel that your conversation was something unique and special and memorable.

15. Put yourself in situations where you’ll get to meet people.
My introverted side screams “No! No! No!” whenever the idea of being in a social situation with people I don’t know well comes up. Almost every time, it’s been well worth it. Any time you get an opportunity to go to a meeting of like-minded people, an opportunity to present, or an opportunity to lead, suck in your nerves and take it on. Almost always, you’ll be glad you did. It will give you many opportunities to interact with and meet people, many of whom you’ll have things in common with – career aspirations, interests, and so on.

16. Have a business card. Period.
I don’t care if you’re not employed or if you’re just working down at your local Burger King. Have some business cards and keep them in your pocket along with a pen. Your business card should have your name, either your current career or your short-term aspiration, and some ways to contact you. You should also have a pen, so you can jot a reminder for that person right on the card. This makes sure that they have a reminder of your conversation in their pocket as well as an easy way to follow up. I give my cards to all kinds of people. In fact, I actually have a couple different variations depending on the situation.

17. Annotate their card (or at least write down their info).
When someone gives you their card at the end of a conversation, annotate it the first chance you get. Jot down what you need to know or remember about this person on the back of that card (yep, with that handy pen you’ve got on hand). This way, when you see the card later on, you can just flip it to the back to know why you wanted to remember this person. This is extremely useful in helping you to sneak this person into your memory, as that type of reminder tends to come along right at that perfect point when you can lock it into your memory.

18. Follow up. Always.
After a meeting, I always try to follow up with any (genuine) business cards or contact data that I acquire. I send a bunch of emails out, just touching base with these people and saying, if nothing else, that I enjoyed the conversation I had with them. I usually start off with a bit of a reminder of who I am and how we met, then I usually try to touch base with something specific we talked about (often jotted on the back of their card). People love to feel remembered, so this is a great way to begin a relationship.

19. Practice. Often.
Life constantly offers us opportunities to practice conversation skills. Strike up conversations with anyone you see: your neighbor, the person on the bus, almost everyone at a convention. The more often you do it, the easier it becomes, and for me (and many others), simply starting that conversation can be the trickiest part.

20. Don’t worry about a failure.
Yes, sometimes you’re going to completely fail at starting a conversation. You’re going to meet someone who’s very unfriendly and ignores you. You’re going to stumble over your words and make a fool of yourself. Don’t let those instances hold you back from trying again and again. The more you do it, the more relationships you’ll build and the easier opening those conversations will get.

Trent Hamm

Founder & Columnist

Trent Hamm founded The Simple Dollar in 2006 and still writes a daily column on personal finance. He’s the author of three books published by Simon & Schuster and Financial Times Press, has contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and his financial advice has been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.