I’ve had a lot of great conversations, and I dislike and avoid small talk. I have found that some of the best begin not with a question but with an observation.
Those contrived conversationy questions, sounding as if they’d come from a popular magazine article entitled “Ten Great Conversation Starters,” tend to invite answers so big (who wants a stranger to start a conversation by asking you about your childhood or your life’s ambitions?) that you blow them off with trivia. They put you on the spot with a message that essentially says “Entertain me. Say something amusing or enlightening. I’ve just thought of the question, and now you are responsible for the answer so we can both stand/sit here with drinks in our hands being deeply and aggressively sociable.” What is that if not small talk?
Much more effective, to me—if the point is not simply to take turns moving your lips while you size each other up—is an observation or comment that somehow ties the present situation to something you know, something you’ve thought about, something you’ve recently read or seen or experienced. It acknowledges some common ground in whatever it is that you are experiencing together while bringing to it something of your own, and it takes the pressure off the other person while you assume responsibility for saying something interesting. Then the person responds or doesn’t—with an equally observant, pithy, witty, charming, or illuminating comment or a question that delves further into your contribution or with a vague smile while glancing around for someone who looks more likely to prefer small talk.
[Edit: While I was typing this, TheBox193 made essentially the same suggestion.]