Some I use. Some were used on me. All of them stuck.
We’ve all sat through the greatest hits.
“Where do you see yourself in five years?”
“What’s your biggest weakness?”
“Tell me about a time you showed leadership…”
They’re safe. And honestly? They’re boring!
The best interviews I’ve been part of, on either side of the table, had at least one question that made the room shift a little. The candidate sat up. The conversation got real. Something was revealed that a rehearsed answer never would have uncovered.
These are those questions
If you had to play a song every time you entered a room for the rest of your life, what would it be?
Why it works: It’s completely unexpected and impossible to prepare for. You see how someone thinks on their feet, how comfortable they are with a curveball, and you learn something genuine about their personality – all in under two minutes.
What you want: A real answer. Delivered with some confidence and a hint of personality. Bonus points if they can explain why without overthinking it.
Watch out for: Paralysis. If someone completely shuts down over a low-stakes fun question, that’s useful information too.
Here’s a piece of paper – draw the route you took from the entrance of the building to get here, and mark all the exits you passed.
Why it works: Most people walk into an interview completely in their head – rehearsing answers, managing nerves. This question reveals whether someone is naturally observant even under pressure. Particularly useful for designers, engineers, project managers, or anyone in a role where environmental awareness and detail matter.
What you want: They don’t need to be accurate to the millimetre. You want someone who has a go, thinks out loud, and can explain their reasoning. Bonus points if they noticed something most people wouldn’t.
Watch out for: Complete blankness or refusal. The task isn’t the point – the response to the unexpected is. And if they genuinely noticed nothing on the way in, that’s useful information too.
Android or iPhone?
Why it works: On the surface it’s nothing. Underneath, it’s everything. How do they defend a preference? Can they argue a position without getting weird about it? Are they a “because everyone has iPhone” person or do they actually have a reason?
What you want: Conviction. Humour. Self-awareness. Any of the three.
Watch out for: “I don’t really mind either.” Sometimes that’s true. Often it means they’ll tell you whatever they think you want to hear.
Tell me something about yourself you don’t want me to know.
Why it works: It’s the most disarming question on this list. It cuts straight through the performance of an interview and asks someone to be genuinely vulnerable – which is exactly what good working relationships require.
What you want: Something real. It doesn’t have to be dramatic. A professional stumble, a gap, an insecurity they’ve worked on. The content matters less than the willingness to be honest.
Watch out for: The humble brag disguised as a confession. “I just work too hard sometimes…” You’ll know it when you hear it.
What would you do if you didn’t have to work?
Why it works: People who have genuinely thought about this tend to be more self-aware and more intentional about the work they choose. It also tells you what actually drives them – which is far more useful than “I’m passionate about this industry.”
What you want: Anything real. Travel, create, volunteer, sleep – it doesn’t matter. You want someone who has an inner life outside of their CV.
Watch out for: “Honestly I’d probably still work.” Could be genuine. Could be performing ambition. Follow up and see which one it is.
How many ways can you think of to find a needle in a haystack?
Why it works: A classic problem-solving question that rewards lateral thinking over correct answers. There is no right answer – which is exactly the point.
What you want: Volume and creativity first, then some logic to back it up. Magnet. Burn the haystack. Hire ten people to search in sections. The more directions they go, the better.
Watch out for: One answer delivered with complete confidence that it’s correct. Problem solvers explore. They don’t just land.
Describe our business to a seven year old.
Why it works: If you can’t explain what you do simply, you don’t understand it well enough. This tests comprehension, communication, and whether someone has actually done their homework before walking in.
What you want: Something clear, warm, and a little playful. They should be able to strip out the jargon and get to the point.
Watch out for: Corporate speak with smaller words. That’s not the same thing.
List six things that make you nervous.
Why it works: Six is a lot. The first two or three are easy. After that, you’re getting somewhere real. It reveals self-awareness, honesty, and how comfortable someone is sitting with discomfort.
What you want: A mix. Professional and personal. Delivered without too much performance.
Watch out for: A completely polished list that sounds prepared. This question only works if it catches them slightly off guard.
What’s the proudest moment of your career?
Why it works: Not just what they achieved – but what they value. The person who’s proudest of a promotion tells you something different to the person who’s proudest of mentoring a junior through a hard year.
What you want: Specificity and genuine feeling. You want to see their face change a little when they talk about it.
Watch out for: Vague answers that could apply to anyone. “Just really delivering results for the team.” Push for the detail.
Who are you?
Why it works: Three words. Infinite answers. It’s the most open question you can ask and the most revealing. Not “tell me about yourself” – which everyone has rehearsed. Just: who are you?
What you want: Something that surprises you. The person who leads with their job title is telling you something. So is the person who leads with their family, their values, or the thing they’re most afraid of.
Watch out for: A career summary in disguise. That’s “tell me about yourself” wearing a different hat. Gently push them further.
The best interview questions don’t extract information.
They create a moment where someone forgets to perform – and just shows up as themselves.
That’s the person you actually want to hire.
What’s the best – or strangest – interview question you’ve ever been asked?
I’d love to hear it.
And if you’re in the middle of all of this right now and need support? DM me. That’s what I’m here for. 🧡
First published in Sarah’s LinkedIn newsletter, Recruitment Rambles. Read the original edition on LinkedIn.
