20 Ways to Start a Conversation and Build Into a Connection
- PUNCH GURUKULAM
- Jun 29, 2021
- 3 min read

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.
4. Listen. When someone is talking, don’t stand there trying to think of the next thing you’re going to say.
5. Touch on elements of rapport. While you’re listening, try to identify elements that you have in common with the person speaking.
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. 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. 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. Ask a question and encourage the other person to fill the conversation space.
12. Have conversation goals… 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. Recognize that 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. 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. 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. 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.
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.
18. Follow up. Always. People love to feel remembered, so this is a great way to begin a relationship.
19. Practice. 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.
FOOTNOTE
Conversations are opportunities to...
Convey Something
Opportunity grabbing
Verify something
Energize Yourself (or) Someone
Rapport Building
Settle a Conflict
Attention Grabbing
Tell a Justification
Impress
Order the Mess
Network Building


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