Glad you asked! Strange but effective interview questions

interviewAny respectable candidate comes to a job interview prepared to answer tried-and-true (though pertinent) questions such as “Tell me about yourself” and “Why are you a good match for this position?” But could it be equally insightful to pose an off-the-wall question such as “If you were a sandwich, what type would you be?”

Many hiring managers routinely venture into unconventional areas for reasons such as judging poise under pressure and measuring creativity. Here, seven leaders discuss the out-of-the-ordinary things they ask and why.

“How many roses do you think were bought on Valen­­tine’s Day in London last year?”

“There isn’t necessarily a right or wrong answer here. What’s much more important is how the candidate comes to an answer. Are they methodological in how they come to the final number, or just provide an educated guess? I feel this can go a long way to showing what kind of person the candidate is.” — Manraj Chhina, customer success manager, Claimable Ltd.

“What is the best book you’ve read in the last year?”

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“Reading is a passion of mine, and finding out what people like to read helps me understand their interests. I get to know each candidate a little better.” — Gregg Parise, CEO at

“If you could be any animal, what type of animal would you be and why?”

“When asking this question, I really want to see how they identify themselves or how they wish to be. For instance, if a person wants to be a lion so that they can rule everyone, it could be a sign that they are bossy or just the opposite. They could be really passive and wish they were more assertive and take-charge.” — Devay Campbell, CEO of Career 2 Cents

“What is the most complicated thing you can think of?”

“Working in the startup world, I frequently interview marketing and technical hires. This unusual question gives me some of the best insight into candidates. (After asking a question) I say, ‘OK, great. Now tell me how you would explain the concept from the previous answer to your grandmother.’ This allows me to gain insight into both a candidate’s technical proficiency as well as how effective they are at communicating technical concepts to people in non-technical roles.” — Elise Gabriel, senior marketing director, Wurrly

“Tell me about the hardest day you ever had.”

“I’m hoping to learn about how a candidate persevered through a tough situation. Did they quit or pull it off? There’s a hiring adage along the lines of ‘hire for character—train for skill,’ and this question definitely probes into that notion of what is this person really made of.” — James Goodnow, attorney, Lamber Goodnow Injury Law Team

“Close your eyes and describe the room and everything in it.”

“After a few standard ‘get to know you’ questions, I always ask candidates to close their eyes and describe the room and everything in it in as great of detail as possible. My agency builds large, complex websites. Attention to detail is crucial. One seemingly minor misspelling or broken link has the potential to really upset a client.” — Chad Coleman, co-founder and CEO of Ascend

“Teach me something from start to finish.”

“We always ask for the candidates to teach us how to do something from start to finish. People teach us how to bake cakes; they sometimes teach us things like how to salsa. We do this to see how thorough they can be in their thought process for completing a single task. If you can teach someone something step by step without skipping a beat, it shows us that you know how to follow instructions.” — Monique Tatum, CEO, Beautiful Planning Marketing & PR (BPMPR)