Ask Better Questions: A Real Life Story of Sales Success


I was out to dinner a few months back with a couple of guests, when the waitress came over to our table as she had done diligently all night and asked completely the wrong question:

“How did you enjoy your meal?”

We all responded that it was fine, that we had enjoyed it and thanked her for asking. Like routine, she moved onto the next, predictable question:

“Would you like to see the dessert menu?”

There is nothing specifically wrong with what she did, and her mannerisms all evening had been excellent. She was doing okay, I guess, but I couldn’t allow her to continue down that path and call myself a real sales expert. So I thought I’d try a little experiment.

I said to her, ask better questions and you’ll get better tips. For instance, don’t ask how I enjoyed my meal because I’m going to give you a polite brush-off answer. Ask instead:

“What was the best thing about your meal?”

The reason, as any seasoned sales professional will know, is that it’s a perfect gateway to a conversation. It’s also a brilliant way to learn. If people repeatedly say the pepper sauce is out of this world, that’s something she can recommend to others as expert advice. It also makes the next, killer move, possible. Rather than asking if we wanted to see the dessert menu, she should have said:

“Now listen, I can’t let you guys go without at least trying one of our desserts. I know you’re probably full, so why don’t I just bring a serving of our chocolate brownies and ice cream with four spoons so the table can share, because they’re honestly out of this world.”


No question. No opportunity to say ‘no’, and no hard sell. Just one extra, low-priced suggestion.


I told her about this and asked her to try it out and call me in a couple of months to see how things are shaping up and I am thrilled to say that she did just that, and that her message was heartening beyond belief.

“I’ve been the top earning waitress in the restaurant since the day I met you,” she said. “Not only am I responsible for selling more desserts every evening than all the other staff combined, people usually buy more than the one-to-share that I recommend. And on top of that, I earn five times the tips I used to earn because people tell me it’s rare to have a waitress who cares as much about them as I do.”

Amazing. And yet, totally predictable.


Ask better questions to engage customers and get them talking about themselves and you’ll increase not only your likeability, but your sales as well.


What better questions could you be asking?

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