1. Have some "deep" conversation starters on hand.
Don't expect substantive topics to instantly spring to mind. Instead, says Tracy Chou, a software engineer at Pinterest, you should approach any interaction with a few deep conversation starters ready to go.
Chou suggests reading some books on behavioral economics and pop psychology and talking about them, "since those subjects are fundamentally about people — and everyone is a person, has to interact with other people, and has opinions about their own behavior and other people's behavior."
She also recommends watching a few TED Talks — "another great source of cool ideas about the world." We suggest starting with some TED Talks that will make you smarter about business.
2. Ask questions about topics the other person is interested in.
Multiple Quora users indicated that one of the best ways to start an interesting conversation is to find something the other person is excited about. Show that you want to learn more about the topic by asking a series of questions about it.
Says Tatiana Esteves: "Try picking a topic that they are really interested in and start with a normal 'shallow conversation.' Then ask quite probing question[s] even if the subject isn't that serious."
For example, Esteves says, "if they like celebrity news, ask them if they think that the 'celebrity culture' is making people less happy with their lives."
3. Find out what makes the other person special.
Whatever you say, writes Joshua Evans, "avoid the awful opening phrase, 'What do you do?'" You'll put your conversation partner in a box where all he can talk about is his job.
Instead, Evans says you should ask, "What makes you a badass? That will induce a chuckle over drinks."
You might even find out something crazy; perhaps they are a lawyer by day and a rock musician by night.
4. Avoid discussing the weather.
So it's three degrees colder than average for December. Big deal.
"Avoid [talking about the weather] like the plague. It's like the black hole of shallow conversation," says Ambra Benjamin, an engineering recruiter at Facebook.
5. Assume the other person has deep thoughts.
"If you assume that there is any possibility that the other person might be dull or will talk stupid, maybe you won't ask things that draw them out in the right way and YOU will ruin the discussion by making it dull," writes Tobias C. Brown.
In other words, assume the other person is just as eager to have meaningful conversations as you are.
6. Don't push people to see your perspective.
If you approach every conversation as an opportunity to convert people to your values and beliefs, you'll probably have a hard time getting anyone to stick around. After all, no one likes to feel like they're being proselytized.
"Don't have too much of an investment in being right or persuading people to adopt your point of view," says Joel Postman.
Instead, be open to hearing about your partner's ideas and at least trying to understand her perspective.
7. Reveal something slightly personal.
"Reveal something about yourself, and discuss how it felt and what you learned from it," writes Jan Leadbetter. "This invariably leads to disclosures from other people. They don't have to be massive secrets or anything like that, just something personal."
Leadbetter's theory is supported by science: Psychologists say that when you disclose something about yourself, other people feel inclined to do the same.
Just be careful not to get too personal. For example, you can mention how you discovered a new favorite musical artist this week — not that you're having a clandestine affair with your coworker.
8. Talk about something specific you're working on.
When someone asks you what you do for a living, don't simply say you're a writer or a doctor. According to Lifehacker, you can liven up the conversation by adding a few details about something you accomplished that week.
Similarly, when you're asked what you do for fun, talk about a recent experience you had doing your hobby, whether that's knitting wool scarves or jogging in the park.
9. Ask for stories, not answers.
It can be tempting to try breaking the ice with an innocuous question like, "How was your weekend?" or "What's up?"
But as Chris Colin and Rob Baedeker write on TED.com, you can elicit some more detail by asking, "What was the best part of your weekend?" or "What are you looking forward to this week?"
That way, your conversation partner can tell a story that allows you to learn more about him and what makes him tick.
