The Gift of Good Questions

Something in us heals when someone asks one of those really good, curious questions.

Sep 17, 2024

Her questions began like most people’s. “Where all did you go?” I answered with my standard answer including the countries visited and a sentence or two summarizing the trip with a nice bow on top. But her question and my answer was just the start of one of the best conversations I’ve had about any of my travels.

Kaylene is an 80-year-old woman with bright eyes I know from church. We became buddies during COVID during long, gabby phone chats about the big and small stuff of life. She called me “Kid” and we’d talk about families and if I ever expressed sympathy for her legs “not working so well anymore,” she’d gloss over it as not a big deal.

When I was back from my first European wander session of 2023, I gave her a call. Not at all to deluge her with an unsolicited travelogue, but to give her the briefest recap of it and to catch up about her life and life in general.

But several minutes later, she was still asking me questions. And what’s more, she was actually listening. A lot of people have asked me about my trip, and I know they cared, but man—Kaylene extra cared. She wasn’t trying to; she was so wonderfully curious. Curious about my experiences, about what was hard, about the places I stayed, about the people I saw. She’s not been to Europe, and she really wanted to know what it was like, in general, and what it was like for me. I had that rare feeling of, “Hey! She’s actually listening to me.” And because she was the one asking questions, I felt comfortable sharing way more with her about my trip and how it changed me than I have with many others.

In a chat this summer about life and families and some challenges in the past couple years, another older friend asked me a direct question, catching me off-guard. “So where do you go for the holidays?” Sounds benign, but I find myself still thinking about that seven-word question, and how seen I felt when she asked it.

In a final example, the woman sitting next to me at a patriotic symphony concert asked me the most interesting-to-answer questions about my corporate experiences. She wasn’t trying to ask me good questions, she just was genuinely interested in my experiences in and out of corporate.

I asked:

I shared the following Note here on Substack wanting to know what others think about good questions:

They answered:

Here are some of the answers people shared in comments or when they re-shared (“re-stacked”) my Note:

The art of a good question is a profound way of letting someone know you see them.

Claire Venus asked us to write 500 words on the topic of rejection. It inspired me to write about it, something I likely would not have written. She’s now including my essay in her soon to be published anthology, The Rejection Palace.

Really good questions make me feel yummy inside. And they encourage me to continue thinking about them long after I’ve answered what initially came to mind. Ripples in a pond from the pebble tossed.

Good questions are often a mirror for me to see from another’s view.

Questions are powerful. A classmate in my coach training cohort asked “What is not taking a break costing you?” It was like turning a lightbulb on in my mind.

Imagine if we all became genuinely curious about one another. We all share a universal need to be seen and understood. What a simple yet profound gift to offer someone.

The art of good questions

I’m not claiming to be the patron saint of good questions and have plenty to learn myself from the good question askers. Here are some of the things I’ve learned about asking good questions and those who do it:

The questions tend to be short and direct versus long and meandering.
There was very little of the asker in the question. The questions weren’t meant to lead anywhere or get a specific answer.
They weren’t meant to be “good questions.”
There was no judgment and criticism or gossip fueling the question.
The asker wasn’t trying to figure out ahead of time how to respond. It’s quite an act of vulnerability and self-trust to ask good questions since you never know what you might get or how you’ll respond to their response. The good news is we don’t really need people to say anything profound in response, just to care.
There was enough trust developed in the relationship or conversation to ask a question that gets a mile beneath the surface, right to the heart.

I sometimes wonder if we are actually able to share our best parts without being asked the “good questions.” Put another way, good questions seem to unlock parts of us we are incapable of unlocking ourselves.

The best news for all of us is that we don’t have to be good with words or super smart or polished to ask good questions. We just have to care about what’s really on the insides of each other and be willing to ask about it.

Your turn:

When was the last time someone asked you a really good question, and really listened to your answer? Comments are open to all on this post, so please share below.