Six Secrets for Starting a Conversation (that the Experts Won’t Tell You)

For most of us, striking up a conversation with a stranger is difficult, and maintaining one is even harder. Use these practical tips to do better at both.

On the stress level, striking up a conversation with a stranger ranks up there with public speaking, taking your driver’s test and visiting the dentist.

Indeed, plenty of books and articles have been written on the subject. Search the words “conversation starter” in Google and you’ll get 7.5 million hits. You’ll get all kinds of advice too from the old standbys (“So, what do you do for a living?”) to the mundane (“How are you doing?”) to the downright bizarre (“If you could teleport by blinking your eyes, where would you go right now?”)

For all their good intentions, the advice-givers tell only half the story. Firing up a conversation is important, sure, but maintaining that dialog is equally critical. How many times have you started a conversation only to quickly run out of things to say? The seemingly endless silence is deafening.

In fact, the whole point of starting a conversation is, well, to actually engage in a conversation. So let’s take a look at ways to both start a conversation and, once it’s going, maintain it.

1. Be complimentary. The easiest, most natural way to start a conversation is one that’s often overlooked with a compliment. After all, who doesn’t appreciate hearing “I really like that sport coat” or “I happened to see you drive up. Nice car!”? A compliment demonstrates your interest and makes for the perfect ice-breaker.
2. State then ask. Most experts advise beginning a conversation with a question, but I’m not so sure. The practice seems intrusive at best, and rude at worst. Instead make a statement, and then follow it with a question. That way you’re giving something of yourself before asking something of the other person. So rather than asking “What did you think of the game last night?” try “That game last night was incredible. Did you happen to catch it?”
3. Avoid the question trap. If you insist on starting with a question, by all means avoid the “question trap.” That’s where someone asks a question as a pretense only to talk about himself or herself. How many times have you been asked, “How’s your day going?” only for the questioner to immediately launch into a discussion of how well (or poorly) theirs has gone. Ask your question, give the other person time to answer and always make sure the conversation flows both ways.
4. Think two steps ahead. Chess players have a game plan and are always thinking several moves ahead of the next one. As conversationalists, we should do the same. Keep the conversation progressing by making mental notes of things the other person has said that interest you and then come back to them later.
5. Be aware and relevant. Current events and pop culture are some of the most popular conversation starters. If you choose one, probe to make sure the topic is relevant to your conversation-mate. If it isn’t, switch gears to avoid bringing the conversation to a screeching halt.
6. Remember, the opening is just the beginning. Once you’ve got the conversation rolling, you need to maintain it. That’s where eye contact, listening intently and asking intelligent questions take over. Check out a recent blog for additional thoughts on how to keep your conversation flowing.

Starting a conversation doesn’t have to the verbal equivalent of a root canal. Follow these practical tips and you’ll easily be conversing with complete strangers in no time.