Last month, a close friend told me he was “doing fine” when I asked how he was handling his breakup. The tone of his voice suggested otherwise, so I followed up: “What’s the hardest part that you haven’t told anyone?” After a moment of silence, he admitted that alongside the pain of the breakup, he was afraid of being alone again and of reentering the dating world after so long. That one question opened the door to the real conversation. I almost didn’t ask and would have missed the chance to truly comfort my friend.
In the busyness of our days, we’re all guilty of accepting the first answer. We ask the first question out of habit, get the usual quick response, “busy,” “good,” “fine,” and move on. It keeps things easy, comfortable, and on script. But the second question breaks the script. And that’s where the real stuff lives.
Years ago, a client didn’t seem like herself during a status call. I asked if everything was on track, and she said, “Yeah, we’re good.” Normally, I would’ve moved on. But something felt off, so I asked, “Is there anything you’re worried about that we haven’t discussed?”
That question opened the floodgates. She’d been quietly watching her team fall behind and didn’t know how to bring it up. Because of that second question, we worked through the problem, shifted gears, and avoided a bigger issue.
The second question doesn’t need to be profound. It just needs to show you’re listening and give the other person space to say more. A simple, “Tell me more,” “What’s really going on?” or “How did that make you feel?” can do the trick. It tells the speaker you’ve heard them and that you’re interested in what’s beneath the surface.
Here’s the part that surprised me: I’m not great at answering second questions. When someone asks how I’m really doing, I tend to deflect, joke, and give another version of “fine.” Just last week, a friend pushed past that and asked, “What’s the hardest part of your day right now?” And suddenly, I admitted something I hadn’t even admitted to myself.
People don’t just want to be acknowledged; they want to be seen. The second question is how we do that. It’s a signal that we’re not just checking boxes, we’re showing up for each other.
Next time someone gives you a canned answer, pause and go one layer deeper. It might change everything.
“Most people do not listen with the intent to understand; they listen with the intent to reply.” – Stephen R. Covey
What’s a second question that’s opened a deeper conversation for you? I’d love to hear it or share this with someone who’s great at asking them.
Have a great weekend.
-Vijay