I'll never forget the year of my life when I lived with my pastor's family in New York. My whole life was in the throes of some trauma around then and my little attic bedroom at their home was safe and warm. There were predictable rhythms in their home: dinner every night, devotions in the morning, guests constantly, really special holidays (and every excuse to celebrate something or someone), and always, always thoughtful questions.
My pastor was the first person I heard use the phrase "Be a 'There you are!' person instead of a 'Here I am,'" and the concept, for me, was life-changing. He modeled in his words and actions, and particularly by his questions, what this meant. He has always been about the other. His intention is to disarm, put at peace, draw out, and care for the person in front of him. And one of the ways he does this is by asking thoughtful questions.
I was painfully shy when I came to live with them, was deeply caught cycles of fear and shame, and struggled to look many adults in the eye, and yet, night after night, we'd be called on to both answer thoughtful questions and ask them. Particularly of our guests. The prompt was, "Lore, do you have anything to ask our guest?" And I'd go into a mad mental scramble trying to think of a question that didn't make me look dumb, when all along, the exercise was mostly to make our guest feel welcomed. Sometimes our questions were rudimentary: Do you like your job? Sometimes they were deep: How did you choose the work you do? Sometimes they ebbed into personal: How do you feel about the work you do? But there were always questions.
I left that home changed in many ways, but the primary of which—and the value I hold most dearly still today, is a desire practice my "There you are-ness" by asking questions. It's one of the questions I get most often from you, dear readers: How do I become a good question-asker?
It's hard to teach this in writing and is best done around folks who are good question-askers. So the first thing you should do is find someone in your community who seems to always ask questions. They're also probably someone who isn't the life of the party or who shines when the spotlight is on them. They might be a bit of a wall-flower, so you're going to have to chase them down and ask your first question: How can I be more like you in this way?
(Actually, that's a great question to ask everyone. "How can I be more like you in this way?" says to the person to whom you're speaking: I see you and I admire this quality in you. That's a good start.)
The first thing to understand about asking good questions is that answerers can see straight through your genuineness. If you're asking questions because you simply want information, it becomes clear almost immediately. If you're asking questions because you simply want to turn a conversation in the direction you want it to go, that also becomes clear. Both are disingenuous. So the first rule of question asking is that it's not about you. It's about them. It's about their heart, their story, their cares, their joys, and their sorrows. The second rule of question asking is: they direct both the information and the direction of the conversation. Think of it like a stream you step into. You don't know if it's going to widen to a river, an ocean, or amble along forever, you're just going to walk in it as long as it continues.
The third rule of question asking, especially if you're a follower of Christ, is our questions should be aimed at the heart of the person to whom we're asking. Most people in most contexts are uncomfortable both asking and answering about the heart. We don't like to intrude and we like less to be intruded upon. But for the Christian, "the matters of the heart are the heart of the matter." As I said, you can't control whether they widen the stream or turn the conversation in another direction, but you can control the question you ask when you first get in.
"How's your heart doing?" is, I think, the easiest way to state your intention (I'm after your heart) and ask a question. People are always taken aback by that question. We're used to being asked about our day or our plans, but our hearts? Ick. Back off. It's a humbling question to ask because the risk of rejection is high for the asker. But the risk of an unchecked heart is greater—and worse—for the one being asked. So risk rejection and ask.
Here are some other great questions to have in your pocket:
How did that situation make you feel?
What did your response to this thing tell you about yourself? God? The other person?
Who told you the lie that XYZ?
What's your story?
Are you where you thought you'd be at this point in life? What would you change? Why?
What's hard for you today? What's a joy for you today?
How can I pray for you?
There's a prevalent belief out there that we always have to have the answers to the questions we're asking. For example, I'm only asking how your heart is because I already know it's a wicked, dark hole that hardly sees the light of the gospel and I'm going to preach at you until the crack of light gets in. But that's not really helpful, not in the long run. How much better to care for the person in front of you by showing interest in their life, heart, fears, and more, and seeing where the conversation goes. The thing you set out to prove might be the final result, but the journey there will be deeper, better, and more like Jesus along the way.
Here's another post I did on why and how Jesus asked questions.