It is the holiday season. This week many of us will have the opportunity to reconnect with family and friends we don’t get to talk with all that often.

Option one: Have a version of the same conversation we have every year. What’s wrong with the [___] (fill in the name of favorite sports team)? What did you think of [___] (fill in the name of recent TV series)? Tell me about your trip to [___] (fill in the name of a recent excursion)?

Option two: Actually learn something about this person in your life that is new, fun, and interesting. The secret? Ask what Esther Choi calls “crazy good questions.” In her book Let the Story do the Work, she outlines different types of questions we might ask.

1: Greatest questions:
What is your greatest [___]? When are you the most [___]? What or who gives you the most [___]?

2: Meaning questions:
What does [___] mean to you? What do you make of [___]?

3: Takeaway or Surprise questions:
What are your takeaways from [___]? What has surprised you the most about [___]? What didn’t you know about [___], but wish you did?

4: The Self questions:
How has [___] experience impacted you? How do you feel about [___]?

5: Different Path questions:
How would [___] be different if you didn’t [___]? If you were to take on the role of [___], how would you handle [___] differently? If you could have any item on your [___] wish list fulfilled, what might those be?

6: Compare and Contrast questions:
What parallels do you see between [___] and [___]? How is [___] different from [___]?

7: Origin questions:
How did [___] begin? What motivated you to [___]? How did people react to your [___] in the beginning?

The final question works wonderfully as a follow-up to all the questions above.
And what else? Or, tell me more about [___].

We live in a world that is defined by the questions we ask. To create a new world, ask a new question.

More tomorrow.


Reflection: Do the questions I ask allow me to learn something new and deepen my relationships?

Action: Track my question-to-statement ratio over the next week.

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