Ways to Start a Conversation and Build Into a Connection

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.

2. Have a current event on your tongue. 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.

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.

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.

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.

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.

8. Remember who people are. 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. 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. 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.

11. Talk less. 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. 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.

17. Annotate their card 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, always try to follow up with any (genuine) business cards or contact data that you acquire.

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.