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A few weeks ago, my family visited my grandma’s cabin in Minnesota. One evening, the neighbors came over for a visit. We had gotten to know these neighbors a bit over the years, so it was nice to catch up.

Going Deep

I was surprised the conversation went as deep as it did. We talked about things like what my great-grandmother was really like, the history of the cabin and the neighborhood, and my dad’s experiences growing up in boarding school. I even learned some new things about my parents and family that I hadn’t known before.

Deep Questions

What caused the conversation to take a deeper turn? I realized that the neighbor consistently asked deep questions. She asked my wife how we met and started dating. She asked my mom what my great-grandmother was like. She asked my dad about his experiences growing up in boarding school. The questions jump-started the conversation. The end result was a much more satisfying and enjoyable conversation.

Staying on the Surface

I was thinking about my own life, and I realized that my conversations with my friends and family rarely get that deep. We talk about how things are going, or how we’re doing, but a lot of times we stay on the surface. We talk about our activities or work, but we don’t really dig in and learn about each other like we did that night.

Shallow Questions

I think the reason for this is that my questions are often shallow and, if I’m honest, lazy. I ask things like, “How’s it going?” or “How’s work going?” or “Anything new going on?” I don’t take the time to dig in below the surface and ask about one’s family or history. I wonder if I could take my relationships to a deeper level by improving the quality of my questions.

Take a Risk and Ask a Deeper Question

The next time you are having a conversation with a friend or family member, take a risk and ask a deeper question. Don’t just ask how their work is going, ask how they got interested in their field. Don’t just ask how the family is doing, ask what their parents and grandparents are like. Where did they come from? What made them tick? Don’t just scratch the surface. Dig deep with your questions and see what happens.

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