Compiled from 50 Reddit threads across r/managers, and r/interviews.
Every hiring manager has their go-to questions. But every now and then, you hear one that makes you stop and think — not because it’s tricky, but because it cuts through rehearsed answers and exposes how a person really thinks.
We went through 50 Reddit threads — thousands of upvotes, stories, and debates — to uncover the most unusual interview questions that hiring managers actually ask, and candidates can’t forget.
What we found was fascinating: Unusual questions aren’t random. They’re psychological tools.
They test curiosity, honesty, empathy, and adaptability — the traits that often predict long-term success more accurately than résumés do.
“If you were a virus, how would you infect a system?”
“How would you secure an airport made entirely of glass?”
These cybersecurity-inspired questions push candidates out of their comfort zone. They reveal problem-solving under pressure and whether a person can think beyond memorized procedures.
Why it matters: Creative hypotheticals show how someone approaches the unknown — a must-have skill in fast-changing industries.
“How are you different today than three years ago?”
“What makes you tick — and what ticks you off?”
Managers in r/managers said these questions uncover self-awareness and emotional maturity. Candidates who can describe their growth — or identify what frustrates them — often perform better in team settings.
Why it matters: You don’t just want skilled hires. You want people who learn from mistakes and manage their triggers.
“What’s your favorite keyboard shortcut?”
“What have you taught yourself recently?”
At first glance, these look silly. But they’re powerful. They catch people off guard, revealing practical curiosity — how they learn, adapt, and stay sharp day-to-day.
Why it matters: Real performance is often found in small habits, not lofty claims.
“Tell me about something you’re most proud of — and why.”
“What kind of work environment helps you do your best work?”
These questions draw out values and motivation. The best candidates light up when talking about their proudest moments — not because they’re bragging, but because passion leaks through their storytelling.
Why it matters: Skills can be trained. Values rarely can.
“What’s your timeline for the hiring process?”
“What challenges is your team currently facing?”
From r/interviews, one of the most upvoted lessons was that confident candidates ask questions back.
They treat interviews as two-way conversations, evaluating whether the company aligns with their goals.
Why it matters: The best hires don’t just want a job — they want a match.
Across 50 Reddit discussions, a pattern emerged: “Unusual” isn’t about weirdness — it’s about authenticity.
The most memorable interview questions are those that:
When your process invites people to show their real selves, you don’t just fill roles — you build culture.
