Getting people to open up in 5 steps:
1. Pay close attention to any information the other person shares at the beginning of an interaction.
2. Establish a point of connection and use that to continue the conversation: “I had a best friend named Nancy,” or “Oh, I heard that you’re from Cape Cod. I’ve been there a couple of times.” If you’re both suffering from the same unpleasant condition (waiting in a long line), comment on your shared misery (“I thought this would be a fast line, but it’s not, I guess”). Leak a little information about yourself, but only a minimal amount to keep things going.
3. Don’t make assumptions. A stranger seated next to you at a reasonably formal dinner may be wearing jeans and a flannel shirt — you may believe that this person got there by mistake, because clearly the person doesn’t fit in to the crowd. Before you write this person off, maintain a generally friendly and respectful demeanor. For all you know, this is someone who didn’t know what the dress rules were or is actually someone wealthy, high-status, and/or nice enough not to care.
4. Ask questions without seeming (or being) nosy and intrusive. Using the data you have in front of you, which could be on a resume or school transcript, start with general questions that you hope will lead to more specific information. You may see an unusually short period of employment or a poor grade on a transcript. There could be many reasons for this, but to get to the truth, give the other person space to put those reasons in his or her own words. If it’s an informal situation, keep your questions to what feels like a comfortable number in the context of the interaction (i.e., don’t get into a game of 20 questions).
5. Figure out when to back off. At some point, the other person may wish to discontinue the conversation or just not answer a question to your satisfaction. That poor grade on a transcript may be due to the fact that a close relative died, or that the subject matter is just one that was too challenging. If you get such an answer, and the individual clearly is upset at talking about the situation, let the matter rest and switch gears.
It’s easy to practice your skills at this form of communication, given how many often we’re in situations with people we don’t really know.