Three unusual questions to make job candidates think

Interviews often default to predictable questions that lead to equally predictable answers. Here’s how to get some meaningful insights into what makes people tick.

For the last dozen years, in hundreds of interviews, I’ve tried to better understand how CEOs hire by asking them: if you could ask a candidate only one question in a job interview, and you had to decide based on their answer whether to hire them, what would that question be?

Yes, I heard familiar questions, such as, “What are your greatest strengths and weaknesses?” and “What are you passionate about?” But my line of inquiry also led to some surprising replies:

“On a scale of 1 to 10, how weird are you?”

“If you were a beverage, what would be your defining characteristics?”

“How would you describe yourself in one word?”

Because people interviewing for senior jobs have faced questions so often as they climb the corporate ladder, most have had practice delivering polished answers to the more predictable ones. You can bet that a lot of people will respond, “I care too much,” when asked their biggest weakness.

And so, almost out of necessity, interviewers have to come up with what I call “bank-shot questions” to peek behind the facades that people present in interviews, so it’s easier to find out what really makes them tick. What’s great about this type of question is that there are no right or wrong answers, and people can’t try to game the system, especially when they explain why they answered the way they did. This led me to wonder: what would be the best single question? Here are my top three from the many I’ve heard.

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The ExCo Group’s Adam Bryant wrote this article for his column in Strategy + Business.