An old friend from my teaching days sat across from me at a diner a few weeks back, and about twenty minutes in, he said something that stopped me mid-bite: "This is the longest conversation I've had with another person in probably a year." Not the longest interesting one. The longest, period. He wasn't exaggerating for effect. He meant it. Between texts, meetings that run on agendas, and family dinners where four people are having four separate conversations with their thumbs, he genuinely could not remember the last time a conversation had gone somewhere he hadn't planned it to go.
I went home and thought about my own week and realized I couldn't remember either. Plenty of talking. Almost no actual conversation — the kind where you don't know where it's going to end up when it starts.
Everybody's Answering. Nobody's Asking.
Here's what I've noticed, in myself before anyone else: most of what passes for conversation now is really two people taking turns talking, each one mostly waiting for their turn to say the thing they'd already decided to say before the other person finished. I do this in ministry more than I'd like to admit. Someone tells me something hard, and while they're still talking, some part of my brain is already assembling the wise pastoral response, the Bible verse, the thing that will make this moment feel resolved. I'm not listening anymore at that point. I'm reloading.
Real conversation — the long, meandering, actually-getting-somewhere kind — requires something most of us have quietly stopped practicing: staying curious about another person past the point where you already think you understand them.
"The purpose in a man's heart is like deep water, but a man of understanding will draw it out." — Proverbs 20:5 (ESV)
I love that verse because of the verb. Not "a man of understanding will wait for it to surface on its own." Draw it out. It takes effort. Deep water doesn't come up by itself. Somebody has to lower a bucket, and lower it more than once, and be willing to come up empty a few times before anything real makes it to the surface.
What David Brooks Calls Being an "Illuminator"
David Brooks spent years researching what separates people who make others feel truly seen from people who, despite good intentions, leave every conversation feeling slightly more alone than before. His finding, distilled down: the difference usually isn't charisma or even kindness in the abstract. It's a specific, learnable practice of asking follow-up questions instead of relating everything back to your own experience. He calls the people who do this well "illuminators" — not because they're unusually brilliant conversationalists, but because they make the choice, over and over, to stay curious about the other person's actual inner world instead of redirecting the conversation back to familiar ground.
Forty-two years married to the same woman, I can tell you the marriages that hold — ours included, on our better weeks — aren't the ones where two people have run out of things to learn about each other. They're the ones where at least one person keeps asking the next question instead of assuming they already know the answer, even after four decades.
Let's Be Honest About the Advice-Giving Habit
Here's my particular version of this problem, and I suspect a lot of leaders and pastors share it: I have spent so many years being the guy people come to for answers that I've trained myself to hear the front half of what someone says and start solving before they've told me the actual problem. At Gateway Mission, this habit doesn't just fall flat — it actively shuts people down. Most of the men and women I sit with there haven't had many people in their lives who stayed curious about them without an agenda. The moment I start problem-solving too early, I've told them, without meaning to, that I've already decided I understand their situation better than they do. I haven't. I rarely do, in the first five minutes.
The Practice That's Actually Changed My Conversations
Before I offer my own story or my own take, I ask one more question. Just one. Not out of technique for its own sake, but because the thing someone says first is rarely the whole thing they came to say.
I let silence sit for a beat longer than feels comfortable. Most of us fill silence to rescue the other person from having to sit in it. Often the most honest thing they'll say all conversation comes right after that uncomfortable pause, if you don't rescue them from it.
I put my phone somewhere I can't see it light up. Not on the table, face down, where I can still feel it buzzing. Out of the room. Presence that can be interrupted at any second isn't really presence.
My friend and I sat in that diner for almost two hours. Neither of us had planned that. It happened because somewhere around minute fifteen, I asked one more question instead of telling my own story back to him, and the conversation went somewhere neither of us expected. That's usually how you know it was a real one.
Who in your life deserves a conversation that lasts longer than either of you planned?