Whether you’re interviewing, pitching, dating or kicking off a meeting, the first question can unlock honesty—or slam the door.
I watched a product manager walk into a glass-walled room and ask the client, “So, what keeps you up at night?” The client smiled politely, blinked, and reached for his water. Silence spread like spilled ink. Three minutes later, they were talking about traffic on the M4.
That’s how it goes when the opener feels canned, heavy, or aimed at a soundbite. People retreat to safe answers or routine banter. The conversation never takes off, even if everyone in the room is smart and well-intentioned.
We came for truth. We got weather chat.
Where opening questions go wrong
The biggest mistake is asking something so vague it begs for a vague reply. “How’s everything going?” nudges people towards autopilot. They’ll say “busy”, “good”, or “you know, same old”. The opener sets the lane. If the lane is foggy, the answer will be too.
Another common miss: the question feels like a test. Start a job interview with “Why should we hire you?” and watch a human turn into a LinkedIn post. On a first date, “Where do you see yourself in five years?” triggers a spreadsheet in their head. In user research I’ve sat through, “Why don’t you use our feature?” leads to a defence, not a story.
Then there’s the triple-whammy question: three asks in one breath. “What did you think of the rollout, what went wrong, and who dropped the ball?” That’s a trap. The brain picks the easiest route—usually blame or avoidance. Openers that stack choices make people choose safety over substance.
Better openers, fewer landmines
Use one clean, neutral, time-framed question. Anchor it in something real. “When you first opened the app this week, what did you try to do?” beats “What do you think of the app?” “What” and “how” draw stories; “why” can feel like prosecution. Let the opener be a doorway, not a demand.
We’ve all had that moment when we ask a big, brave question and then instantly wish we could edit it mid-air. The fix is simple: slow down, go smaller. Start where the person already is—today, this morning, the last time they tried X. Let’s be honest: nobody actually does that every day. If you dread silence, count to three in your head after asking. Answers grow in quiet.
Start with the human, not the script. A veteran interviewer once told me,
“Your first question should be easy to answer and hard to fake.”
Try this quick pre-flight before you open your mouth:
- One thing at a time: strip the question to a single ask.
- Swap “why” for “what” or “how” to lower the guard.
- Time-box it: “this week”, “last time”, “earliest moment”.
- Use their words: mirror a phrase they just used.
- Invite choice: “Would you like to start with A or B?”
Leave the door open
Think of the opener as lighting a small lamp, not firing a flare. A modest, grounded question earns trust, and trust invites detail. This is where the room either opens up or shuts down. If you feel the urge to impress, breathe and ask for a scene, not a summary. A good opening question invites a story, not a verdict. If the answer comes as a list of slogans, pivot gently: “Could you walk me through the last time that happened?” And if the response is short, resist the rush to fill it. Silence after a question is not a bug; it’s a feature.
| Point clé | Détail | Intérêt pour le lecteur |
|---|---|---|
| Shape the lane | Use specific, time-framed “what/how” prompts | Gets past small talk to real material fast |
| Ask one thing | Remove double-barrel and leading language | Reduces defensiveness and confusion |
| Hold space | Pause after asking; listen for the second answer | Unlocks deeper, more honest stories |
FAQ :
- Are “why” questions always bad?Not always, but they’re risky as openers. Start with “what” or “how”, then move to “why” once rapport is warm.
- What if the person gives one-word answers?Reflect and narrow: “You said ‘busy’. What filled your morning between 9 and 11?” That invites a scene.
- How do I avoid sounding scripted?Write your opener, then say it out loud and cut three words. Use the other person’s last phrase when possible.
- Is it okay to challenge someone early?Challenge the situation, not the person. Ask, “What made that tricky?” instead of “Why didn’t you…?”
- What’s a safe opener for any setting?“Where would you like to start?” It offers control, shows respect, and reveals what matters most right now.
