(Photo courtesy of Dennis Brendel )
Ever felt like your conversations are stuck on repeat? You know the drill—“How’s work?” “What do you do?” “Seen any good movies lately?” Yawn. These questions are so predictable they might as well come with an eye-roll emoji. And while they serve a purpose, they’re not exactly the kind of questions that make someone’s eyes light up or spark a memorable conversation. But here’s the good news: a small tweak in your approach can turn a boring chat into a meaningful exchange.
If you really want to know what makes someone tick, asking direct questions like, “What are your strengths?” or “What do you value most?” won’t get you very far. Why? Because they make people freeze up or, worse, give canned, over-thought responses. Instead, try catching someone off-guard with a more playful, indirect approach. These types of questions slip under the radar and get people to open up without feeling like they’re being interviewed. The magic of indirect questions is that they let you learn a great deal about someone’s interests, values, and worldviews—without ever mentioning these terms.
Imagine asking, “What’s something you’re terrible at, but love doing anyway?” This question might get a person talking about their passion for karaoke, despite the fact that they sound like a yowling cat after three espressos. Without saying it explicitly, you learn they’re someone who values fun and doesn’t take themselves too seriously. Or try, “If you had a whole day to yourself with no plans, what would you do?” Instead of asking about goals and priorities, you’re indirectly learning what they find relaxing, exciting, or fulfilling.
Even mundane topics can yield surprising answers. Think about the question, “What food can you not stand?” You’re not just learning about taste preferences; you might uncover a quirky childhood story or a surprising cultural background. That’s the beauty of these indirect questions—they open the door to personal stories that go beyond surface-level facts.
The strategy here is to ask questions that disarm, surprise, or make someone laugh. When someone has to pause and think for a second, you’re already halfway to a better conversation. It’s like taking the scenic route instead of barreling down the freeway. You’ll uncover more nuances, side paths, and unexpected destinations. Here are a few other clever prompts you can use:
- “If you could have a conversation with your 15-year-old self, what would surprise them the most about who you are today?”
- “What fictional character do you think you’d get along with best?”
- “What’s your favorite ‘guilty pleasure’ TV show that you’re not really embarrassed about?”
- “If you were to spend a full day with a super-hero or someone you admire, who would it be and what would you do?
See how these questions don’t feel like the typical, box-checking inquiries? Yet, they invite revealing and meaningful responses without being too on-the-nose.
There’s a psychology behind this, too. People tend to reveal more about themselves when they feel like they’re not being put on the spot. Indirect questions lower the defenses because they’re framed in a more casual, non-threatening way. They don’t feel like they’re under the microscope, so they’re more likely to give answers that reflect who they really are, instead of who they think they should be.
It’s also about flipping the usual dynamic. Most people are used to being asked what they do, not how they think. And when they’re given the space to think aloud about something unexpected, it often brings a spark of joy or a genuine smile. And that’s the golden ticket to better conversations—when you can make someone feel seen and heard, without ever explicitly stating, “Hey, tell me your deepest thoughts.”
So, next time you’re in a conversation rut or want to skip the small talk, give indirect questions a shot. Who knows? You might find out more about a person in five minutes than you would have in five weeks of “What do you do?” conversations.
Because, really, the art of great conversation isn’t about asking perfect questions—it’s about asking the right ones. And those are often the ones nobody sees coming.
Bob Fagan has just published “The Little Book of Questions That Matter — A Lifetime Companion For Transforming Your Life.” It is available on Amazon.
