Revealing Job Interview Questions to Ask Candidates

Our Bartleby columnist asked readers of his newsletter for a favourite job interview question — one that reliably says the most about a candidate. Here is a selection of their replies, edited for brevity.

Interview questions about curiosity and background

What was your favourite subject — and what did you learn?

This is a question for new graduates, in two parts: Part 1. What was your favourite subject at university? Part 2. What did you learn in that subject? The best answer ever: “That was nine months ago, I don’t remember.”

Dr Bob Warfield

What did you last read, and what do you do in your spare time?

I may be a dinosaur (I’m 55), but I often ask, “What was the last book you read?” I will also ask, “What do you do in your spare time?” Neither of these questions is revolutionary but do help me in my quest to identify candidates who are curious, an attribute that I find important.

Yvonne Hilst

What sets you apart from your peers?

“What sets you apart from your peers?” It helps me determine if the candidate studied the role and its responsibilities, the company and perhaps most importantly, themselves.

John Prieto

Interview questions that test quick thinking and personality

Why are drain covers always round?

“Why are drain covers always round?” This question is intended to show how one can think quickly on one’s feet and display some humour depending on the answer. Answers could be: round covers cannot fall into the drain hole; round covers roll down the street after a comical explosion.

John Jackson

If we gave you a blank cheque and a free weekend?

My favourite towards the end of an interview: If we gave you a blank cheque and a free weekend, where would you go, what would you do and who would you go with? The answers were always interesting and sometimes very revealing.

Kate Siviter

What is the most positively outrageous thing you’ve done?

My favourite is “What is the most positively outrageous thing you’ve done?” The way the answer is provided tells a great deal, from moral calibration, to the ability to react to unusual situations and a readiness to be unconventional. I started to use it after seeing a job advertisement by Southwest Airlines in the 1990s, which said it was looking for employees who are positively outrageous.

John Lumsden

Would you help us wash the dishes?

My father, who passed away a long time ago, would have dinner at our cabin with a candidate and ask, “Would you mind helping us wash the dishes?” The conversations that would follow were often revealing of personality as it is more difficult to keep up pretensions with your hands in the dishwater, or passing a not clean enough dish back for more scrubbing.

Dick Wilson

Do you share my sense of humour?

I’ve been on both sides of the desk for job interviews and a critical characteristic in either direction is a compatible sense of humour. I would insert a reference to Monty Python or Hitchhiker’s Guide or Star Trek and see what response it got. A grin was sufficient to let me know I would be comfortable working with that person, or department. I have found that a lively sense of humour correlates pretty strongly with traits such as flexibility, curiosity, friendliness, and so on. If there’s no grin, run away! run away!

Miki Magyar

Interview questions about failure, achievement and honesty

Tell us about something you tried that didn’t work

Talking academe here. I personally liked the question, “Tell us a joke.” Unfortunately, the other members of the hiring committee (probably with no sense of humour) went crazy and I had to withdraw my request. One request that didn’t get bombed and provoked interesting responses was: “We all want to talk about our accomplishments, but tell us about something you tried that didn’t work.”

Harold Gotthelf

What do you wish you had known before you started working here?

My favourite question to ask is “What do you wish you had known [about the prospective employer] before you started working here?” It tends to catch people off guard and, thus, elicit an honest response.

Yvonne Hilst

Not including work or family, what is your biggest achievement?

This is always my last interview question, which I have used probably more than 60 times in the past ten years. The first time was by chance and seemed a logical next question, to me at least, but not to the candidate. The candidate was in full flow, very confident, full of experience both professional and personal, so I asked: “Not including work or family, what is your biggest achievement?” It floored him, he stopped and erred and turned into a wreck in front of me. Not that I wanted that; I thought I was showing interest in his experiences. It’s a question nobody seems to anticipate and hence practise. It shows me quickly how a person reacts in an unexpected situation. I’ve had a number of really good answers, some very personal answers too. Only once, did someone ask me “So what’s your answer”?

Tim Kilpatrick

What will your last manager score you out of ten?

“What will your last manager score you out of ten when I call to talk through your reference?” It being important the candidate understands that you mean to make that call and ask that question. I recall a candidate squirm as she replied “I realise how bad this could sound, but I know he will say ten, but I’d feel more comfortable saying nine.” Lo and behold, he did say ten, and yes, I still regard her as one of the greatest hires I ever made.

David Schluter

Tell me about a time that you have failed?

“Tell me about a time that you have failed?” That question gives an insight into accountability, humility, ability to reflect and learn, and communicate difficult messages. If you haven’t failed at anything, that’s also a definite alarm bell. Helps identify the narcissists.

Katrina Ford

Tell me what you have been doing since you got out of prison?

“Tell me what you have been doing since you got out of prison?” Most people laugh nervously and become less extravagant in their claims. A few don’t laugh at all and are out of consideration for the job.

Mervyn Taylor

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