How to get people to share personal information

“It is conversation, not interrogation.” This is a request I received while conducting interviews with high net worth individuals for my book, Captivating the Wealthy Investor. The setting might be social or business but asking question after question can be unsettling. Think about when your family doctor asks, “How often do you drink alcohol?” and the questions that follow. You become defensive.

Give to get. You are at a social event, chatting with a person you just met. You want to draw them out. If you ask questions, they might wonder, “Why do you want to know?” A good strategy is “give to get” or volunteering information to get information. Instead of asking, “Where do you live?” you might say, “My wife and I live on Broadway, just off 68^th Street.  What about you?” Volunteering information softens your request.

Softly, softly. Another approach is to use comforting phrases and questions. Another way of asking “Where do you live?” is “Where’s home?” The word “home” brings up good feelings.

Observation. Yogi Berra gave us great quotes, and one of them is, “You can observe a lot by just watching.” Look at the person across from you. Notice their jewelry, tie, watch, hair style and clothing. Are they carrying a book? Do they wear glasses? Do they have a lapel pin? (Many people wear an American flag pin.) This provides an opening to offer a compliment.  “That’s a beautiful ring. Is it a family piece?”  They might explain they collect Art Deco jewelry.

Finding their passion. The quietest person in the room can be the most interesting. Get them to talk about their passion. The person with the great watch might collect timepieces. The person attending the historical society event might be passionate about land preservation. This can backfire, so be careful. You might generally assume people connected with the chamber of commerce are interested in development and growth. People at the nature conservancy or the historical society are focused on preservation. Mentioning the new mega shopping center recently approved is not the best way to start a conversation at the nature conservancy. You will discover people’s passions the hard way!

The negative answer followed by more information. You know some monosyllabic people. Most of their answers are yes or no. Do you like tennis? No. How about golf? No. If you are on the receiving end, you can give them something to work with by sharing more details. “Do you play tennis?” might be followed with “I don’t play tennis, but I love squash.”

Now we get into inferences, making assumptions.

Work related questions. “What do you do?” is a classic icebreaker question. It reveals more than people might imagine. If you have done prospect research beforehand, you know what that profession pays in your local market. You know how much education was required. You know whether the job requires a license.

Where do you live? This is the other icebreaker question. Even if their answer is short in details, you know property prices in your area. Is the neighborhood prestigious? Is the area only zoned for large properties? You might know if they are in a development or an apartment building. Is it likely they are in new construction or a historic structure? Do they have lots of acreage around their property? Is there a homeowners association? You can draw several inferences from a little bit of information.

Where do they play golf? This assumes they live in the suburbs, and they are golfers. Do they play at a private club? You know the exclusive ones. Is it tough to get in? Are the annual costs of membership high? Do they host famous tournaments?

What type of car do they drive?  You have heard the saying, “You are what you drive.” People often buy a car that suits their personality or their aspirations. If they have an exotic car or a classic sports car, the carrying costs can be high. Maintenance is expensive. If they have a car like that, it might be a passion.

What other organizations do they belong to? This can reveal shared interests. You are meeting them at one event. What’s their connection to the organization? What other local causes do they support? This can be a “give to get” opportunity to share information.

What other events will they attend? You have met them at an event. You might have chatted about other organizations they support. What other events do they plan to attend? If you meet several people who you think have friend and prospect potential, this is important. If five of them will be attending the Concert in the Park next weekend, you should attend too. It’s an opportunity to walk around, saying hello to familiar faces.

You can learn a lot about people without seeming intrusive.  Simply ask the right questions!

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