1. Skip the small talk
“What’s up with this weather?” and “How ’bout them [insert local sports team]?” are as bad as cheesy pick-up lines when it comes to starting a conversation. Avoid tired topics. Every situation is unique, so you should be able to find a unique conversation starter.
2. Ask for their opinion
Everyone has one! For someone you don’t know well, start with light subjects like the food, the music, the atmosphere, etc. “Do you like your Margaritas with salt or without? Do you like this song?” It’s probably best to stay away from really sticky subjects like politics unless you already know the person very well.
3. Ask for their advice or recommendations
This works very well when commenting on someone’s outfit or accessories, as in “What a great tie! Where did you get it?” or on the food, as in, “Everything looks good. What are you having?”
4. Ask them a question — that’s easy to answer
This is great when you know or find out that a person has expertise in a particular field. If you’re talking to your company’s IT guy, for example, you could ask him whether he’s the guy who installs hardware or software. But avoid asking anyone to explain something super complex or involved; if that’s where the conversation leads, great, but asking a really complicated question up front can feel demanding.
5. Comment on the environment
No matter where you are, there are things to comment on: the music, the food, the lights, the guests, and so on. Even if you are stuck in an elevator with someone, you can comment on the music, the speed, the crowdedness, etc.
6. Ask for an update
If you know someone a little or know them by reputation, ask for an update on something you know they’ve been doing, for example, “Oh, Mary mentioned you were taking swing dance classes. How’s that going?”
7. Ask open-ended questions whenever possible
If your question can be answered with a simple yes or no, don’t be surprised if that’s what you get. Having follow-up questions ready can also help the conversation flow. If you are asking what kind of food they’re having, for example, you might follow up with, “That sounds good. Do you know what kind of wine would go well with that?” Almost everything can be followed up with, “Why?” (Just don’t ask it too many times and end up sounding like a three-year-old!)
8. Ask a hypothetical question
These can be great conversation starters, but try to tie them into something happening at the event or in current events to avoid seeming too random. You might say something like, “I just saw this movie where all the laws were revoked for one day. What would you do if there were no laws for a day?”
9. Ask about their kids, pets, or hobbies
People love to talk about the things that are important to them. If you know that your boss loves to sail, asking him about his latest trip is a surefire way to get him talking.