The situation

You’re at a charity event supporting breast cancer research at the Ritz-Carlton.

It’s black tie, complete with a chamber orchestra, silent auction and champagne. You’re surrounded by wealthy prospects and see one standing alone—a fashionable, middle-aged woman.

How can you talk to her without sounding like a fool?

Charity events are full of opportunities to connect with affluent prospects. But before you commit to going, find out who’ll be attending. Then do an Internet search for topical issues so you have some conversation starters. For instance, if it’s an event for pharmacists, you could ask people what they think about Loblaws’ recent acquisition of Shoppers Drug Mart. At the event, make eye contact with the prospect and approach her with a smile. Give her a strong handshake and introduce yourself.

Read: 5 tips to prospect wealthy clients

To put her at ease and encourage friendly conversation:


Sounds like a great charity. How are you connected to the event?


Is that your name on the gold sponsor list?


Have you been enjoying the evening?


Do you go to a lot of these swanky events?


How did you get started in your career?


Do you make a lot of money as a CEO?

Break the ice with a compliment. Say, “That’s a beautiful necklace.” Or ask a simple question that will evoke a positive response, like, “Are you enjoying the evening?” Odds are, the other person feels just as awkward as you do when meeting new people, so this will help both of you feel comfortable.

Then, ask open-ended questions or make statements that encourage her to talk about herself and her interests. For example, you could say, “Tell me how you found out about this event. Sounds like giving back to community is important to you.”

Read: How to properly wine and dine clients

And read her body language, including gestures and facial expressions. This will tell you how receptive she is to the conversation. If she’s happy to talk to you, she’ll maintain eye contact, nod and smile. But if she keeps looking around or checking her watch, then it’s time for you to excuse yourself and walk away.

Tips for a good conversation


  1. Give your full attention to the other person. Nod, smile, have eye contact and say, “Yes,” or “Uh huh.”

  2. Paraphrase and be sincere. For example, “Did you say that you had an accident? Sorry to hear that.”

  3. Share in the conversation and also pause to consider what you’ve heard.


  1. Exploit sensitive information. If you jump in with “Is that really your yacht in the harbour?,” it’ll make the prospect uncomfortable.

  2. Slouch, play with your hair, tap your foot or look around the room—you’ll seem uninterested.

  3. Be clingy. No one likes that.

  4. Hold your drink in your right hand. It’ll result in wet, cold handshakes.

  5. Carry a huge plate of food. You’re there to network, not eat.

  6. Run out of business cards.

Conversation non-starter

Is that a real