Asking Real Questions: The Second Question Is Where the Conversation Is

“How are you doing?”

“Good. Busy. You?”

“Yeah, same.”

That’s probably the most common conversation in any church lobby in America. Two people talked to each other, and neither one learned anything true about the other.

Now picture those same two men at a breakfast table. One of them asked the other to meet with him once a month. There’s coffee and an open Bible and an hour to spend together, and the conversation is going to go exactly the way it did in the lobby, because the first answer to any question is rarely the real answer.

The real answer usually comes after the second or third question. That’s where the conversation is. Most of us never get there, though. We stop asking and start talking.

The first answer is the lobby answer

When someone asks you how you’re doing, you know exactly what to say. Everybody does. It’s nice and quick and polite, and it keeps you from giving too much away. It’s the lobby answer.

The lobby answer isn’t a lie. I think of it as a door. The person is checking whether you actually want to come in.

When you take the lobby answer and move on, you’ve told them, without meaning to, that you didn’t. When you ask a second question, you’ve told them you did.

Scripture has a line for this:

The purpose in a man’s heart is like deep water, but a man of understanding will draw it out. (Proverbs 20:5)

Deep water doesn’t come up on its own. You lower a bucket, and then you lower it again. A good question works the same way. The first one finds the surface, and the second and third go down to where the water is.

Jesus asked more than he told

We tend to think of Jesus as the one with all the answers, and he is. But if you read the Gospels with a pencil and mark every question Jesus asks, you’ll wear that pencil down. He asks questions of his disciples and the crowds and his enemies and people who are hurting.

Look at Mark 10. A blind man named Bartimaeus is sitting by the road outside Jericho, shouting for mercy. The crowd tells him to be quiet, and he shouts even louder. Jesus stops and has him called over. Then he asks him:

“What do you want me to do for you?” (Mark 10:51)

Think about that. The man is blind. Everybody on that road knows what he needs, and Jesus knows better than any of them. He asks anyway.

Why? I think it’s because the question treats Bartimaeus as a person and not a project. It lets him say it out loud and gives him a part in his own healing. The blind man answers: “Rabbi, let me recover my sight” (Mark 10:51). Now it’s his request, in his words.

There’s another detail I love in this passage. Just a few verses earlier, James and John asked Jesus for a favor, and Jesus asked them the same question he’d later ask Bartimaeus: “What do you want me to do for you?” (Mark 10:36). James and John wanted the best seats in glory. Bartimaeus wanted to see. Same question, two very different hearts. Good questions don’t put anything in. They bring out what’s already there.

If the Son of God asked before he fixed, you and I can afford to.

How Jesus worked a conversation

John 4 is the clearest picture we have of Jesus in a long one-on-one conversation. A Samaritan woman comes to the well at noon, and Jesus is sitting there, tired from the road.

Watch how it unfolds.

He starts with something small and ordinary: “Give me a drink” (John 4:7). It’s a request, not a sermon, and it surprises her, since Jews and Samaritans didn’t share cups.

Then he offers something that makes her curious: “If you knew the gift of God, and who it is that is saying to you, ‘Give me a drink,’ you would have asked him, and he would have given you living water” (John 4:10). She pushes back. He doesn’t argue. He keeps going.

Then, at verse 16, he goes beneath the surface: “Go, call your husband, and come here.” She gives a lobby answer: “I have no husband.” Jesus doesn’t let it slide past, but he doesn’t crush her either. “You are right in saying, ‘I have no husband’” (John 4:17). Then he names what’s under it: five husbands, and the man she’s with now isn’t her husband.

She tries to change the subject to a religious argument about which mountain is the right place to worship. Most of us would take the bait. Jesus answers her briefly and brings it right back to the real thing, to true worship and the Father seeking worshipers and finally to who he is.

He starts small and he’s patient in the middle, and he keeps going past the first answer and doesn’t take the detour. And at the end she runs into town saying, “Come, see a man who told me all that I ever did” (John 4:29). She isn’t humiliated. She’s free. When you’re known by someone who doesn’t walk away from you, you’re free.

You and I don’t know the heart of man the way Jesus did. But we can learn his patience and keep asking past the lobby answer.

Open questions and closed questions

This next part is mechanical, and it’s worth learning the way you’d learn a tool.

A closed question can be answered in a word. “Did you have a good week?” “Are you reading your Bible?” “Is work going okay?” Yes. No. Fine.

An open question can’t. “What was the best part of your week?” “What’s been hard about reading lately?” “What’s work been like since the new boss came in?”

Closed questions aren’t evil. Sometimes you just need a yes or no, and a lot of accountability questions are closed on purpose. I’ve written about those in my post on Questions to Ask an Accountability Partner. But closed questions tend to end a conversation, and open ones start one.

Most of the time the fix is simple. Swap the first word. “Did” and “Are” and “Is” tend to close. “What” and “How” and “Where” tend to open.

• “Did you pray this week?” becomes “What was prayer like this week?”
• “Are you and your wife okay?” can be changed to “How are things at home, really?”
• “Do you understand this passage?” becomes “What stands out to you here?”

The second and third question

Once you’ve asked a good first question, your next job is not to waste the answer.

The second question comes from what they said. Not from your list, and not from whatever you planned to talk about today, but from their words.

He says, “Work’s been rough.” The lobby move is “Sorry, man,” and on to something else. The second question is, “Rough how?” He says, “My new supervisor rides me all day.” Third question: “What does that do to you when you get home?”

Now you’re somewhere. You’re talking about a man who comes home angry and takes it out on his kids and is ashamed of it. You’d never have gotten there from “How are you doing?” You got there because you asked three times.

A few second questions that work almost anywhere:

• “Say more about that.”
• “What do you mean by ___?” (use his exact word)
• “What did you actually say to him?”
• “How did that land on you?”
• “What do you think God is doing in that?”

“Say more about that” is probably the most useful sentence in discipleship. It costs you nothing, it works every time, and it tells the other person you’re still listening.

Sitting in the silence

At some point you’ll ask a question and they won’t answer right away. They’ll look down at their coffee and not say anything.

That’s the most important moment in the conversation, and it’s the one most of us ruin. We can’t stand the quiet, so we fill it. We rephrase the question, or answer it for them, or tell a story about ourselves.

Don’t. The silence means they’re thinking. A lot of times it means they’re deciding whether to tell you the truth. If you jump in, you’ve handed them a way out of that conversation.

Count to five in your head. Count to five again if you have to. Let it be uncomfortable. The five seconds after a hard question may be the most important thing you do all morning.

Job’s friends get a bad reputation, and they earned most of it once they opened their mouths. But read how they started: “And they sat with him on the ground seven days and seven nights, and no one spoke a word to him, for they saw that his suffering was very great” (Job 2:13). Honestly, that week was the best ministry they did. The trouble started when they stopped sitting and started explaining.

Resisting the urge to fix

This is the last skill, and for most of us it’s the hardest, especially for men and especially for anybody who’s good at solving problems. I spend a lot of time around a car repair shop. When something’s broken, my instinct is to grab a wrench.

But people aren’t carburetors. When someone tells you something hard, they almost never need the fix in the first ten minutes. They need to be heard all the way to the bottom of it. If you fix it too early, you’ll fix the wrong thing, because all you heard was the lobby answer.

If one gives an answer before he hears, it is his folly and shame. (Proverbs 18:13)

James says it more briefly: “let every person be quick to hear, slow to speak” (James 1:19). The time for counsel, for Scripture, for a word of correction will come, just later than you think. You earn that right by listening.

A good rule: before you give any advice, ask one more question. “What do you think you should do?” You’ll be surprised how often they already know.

Your practice this month

Have one conversation where you only ask. Pick a real person, ideally the one you’re investing in. Coffee, a drive, a lunch break. For the whole conversation, your job is questions. No advice, no stories about yourself, no fixing. If they ask you something, answer briefly and then ask them something back.

Afterward, sit in the car before you drive away and write down the three best questions you asked. Not the three you planned. The three that actually opened something.

You’ll learn more about that person in one hour than in a year of lobby conversations. And you’ll probably learn something about yourself, too, like how badly you wanted to talk.

The first answer is the door. The second question is how you walk through it.

This article is part of The Investors, a two-year leadership track at Living Faith Church for people who are ready to pour into someone else the way someone poured into them.

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