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I was in the midst of a fascinating conversation with a favorite 6 year old. My mother was visiting too and she mentioned what a pleasure it was because the child answered my questions in full sentences and fun stories. In the same breath, she talked about how frustrated she feels when she tries to have a conversation with a different child because that young person answers her questions with just one word responses.
Then, as I tell the child I’m going to get more blueberries for him (because he polished off the ones that had been on his plate), I hear my mother ask him: “So, do you like blueberries?” “Yes!” he says.
You have to ask good questions if you want good answers! 
Ask a yes/no, standard, “duh” type question and get a yes/no bored “duh” answer.
Sales person to prospect*:
Do you have a few minutes? No.
Are you familiar with our hotel? No.
May I send you more information about the hotel? Yes. (Please. Anything to get you off the phone, wasting my time and then I can delete whatever you send.)
Reservation Sales person to phone in caller*:
How many people in your party? One.
Have you been here before? Yes.
May I tell you about our packages? No, I’m good. Thanks.
Front desk to traveler*: 
Where d’ya come from today? Arizona.
Did you have a good trip? Yes.
Is this your first visit? No.
My mother to 6 year old*:
How was school today? Good?
Is your teacher nice? Yes.
What subject do you like best? Reading.
Solution: 
• Ask questions that are interesting for the other person to answer; questions that are worth their energy and time and thoughtfulness.
•Ask questions that require more than one word responses – especially if those one word responses are going to be yes/no.
•Ask questions that elevate and extend the conversation not shut them down because the other person feels foolish or stupid.
•Ask questions that are easy for them to answer yet still provide more than one-word. Try a provocative question with 2 different thoughtful answers:
Sales person to prospect:
In working with 12 month loans bad credit and other financial industry partners, we’ve noticed that privacy and comfort are really important to the success of their meeting. Are these key drivers for you or is it something else?
Reservation Sales person to phone in caller:
You mentioned that you’re looking for a room for your husband and yourself for his birthday. I’m wondering if you’ve had a chance to look at the awesome packages we have for special occasions on our website or if you would like me to provide some fun suggestions to make this an unforgettable weekend?
Front desk to traveler:
Welcome to Boston! What a perfect time to be in our historic city! I’m wondering if you would like to have information about where you can eat the best pizza or Boston chowder, or maybe you have time for a walk/run (personalize by looking at the person!) and I can show you a map?
My mother to 6 year old:
When I was in school, I loved reading about children who could do things I couldn’t. Do you read stories like that or what is about reading that is so fun for you?
Asking better questions doesn’t guarantee the best conversation. But asking good questions, even if the answers are perfunctory, will yield important insights into how you can build authentic rapport and maintain a meaningful relationship.
*These original questions could also work to start an insightful conversation if:
-the person asking them is genuinely interested
-the person asking doesn’t immediately start talking about his own experience in an effort to bond, or otherwise (as in, “Oh I was in Arizona once when I was 5. I remember it was really hot and we went to the Grand Canyon.”) Really?
-the person follows up with an insight-based question using the bits of information gained

What are great open ended questions you use to enable an interesting conversation?

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