Even the best questions can feel awkward if the delivery is stiff. Start with context. If you’re grabbing coffee, tie the question to something immediate: the place, the moment, or a shared topic. That simple move changes the tone from “testing” to “connecting.”
Then, aim for “inviting” questions—ones that sound like you’re genuinely interested. A useful guideline is to ask about experiences and preferences, not just general opinions. People have stories. Opinions can be abstract.
One more practical detail: follow-ups matter more than the first question. If someone says they love hiking, “Cool—what got you into it?” works better than “Oh, I guess that’s nice.” You’re showing you’re listening, not just collecting answers.
Follow-up prompts that keep momentum
If you want the conversation to keep moving, try adding one of these after their answer.
- “What was that like?” (turns details into story)
- “How did you get started?” (creates a timeline)
- “What surprised you?” (reveals perspective)
- “Is that still true for you?” (adds change over time)
- “What do you wish more people understood?” (invites values)
