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4 Unexpectedly Great Interview Questions to Ask Anyone

by Hanna Brooks Olsen
featured, money & life

interview questions

Image: Evan Forester via Flickr

Here’s a fact that will surprise no one: Boring questions elicit boring answers. Where are you from? A place. What do you do? A job. If you really want to find out more about someone, you’ve got to have the kind of interview questions that make a person think before they answer, and give you a better idea of who they are and what they’re about.

“The secret to asking great questions is avoiding generalities or broad philosophical inquiries,” explains New York Times reporter Jodi Kantor in a Quora thread. “Hypotheticals are worst of all, because they’re going to give you the opposite of what you want, which is the person’s real, lived experience.”

Good interview questions can change everything — they can give you the perfect story for your blog, or help you find the best candidate for a job. Regardless of why you’re interviewing someone, it’s smart to have some clever questions chambered.

So what makes a great interview question?

First, a rule that all reporters know by heart: No yes-or-no questions.

“The best questions are open-ended,” writes Chip Scanlan for Poynter. “They begin with ‘How?’ ‘What?’ ‘Where?’ ‘When?’ ‘Why?’ They’re conversations starters and encourage expansive answers that produce an abundance of information needed to produce a complete and accurate story.”

Alex Blumberg, co-founder of Planet Money and long-time producer for This American Life, agrees.

“You don’t want to ask a yes-or-no question, because that’s the end of a story. How you ask the question is very important,” he explained in his CreativeLive class, “I often say ‘tell me about the time when…’

By starting your question with “tell me,” you’re immediately starting the conversation with something that will lend some explanation. For a job interview, you might ask something like “tell me about a time when you were challenged in the workplace.” Even though this isn’t even really a question, it allows the person to answer with some detail, as opposed to “have you ever been challenged in the workplace?”

In fact, many of Alex’s questions aren’t really questions at all — they’re prompts.

You may also ask directly for a story, with “tell me the story of…” This is a great interview question in and of itself, but it’s also a good follow-up to a simpler question, or a question that didn’t get the result you wanted. If your interviewee is reticent to give up information, prompting directly for the story might be exactly what you need to do.

Another great way to get people talking is to ask them to walk you through something.

“Something that often works well is if people can talk through a process,” he says “so ask ‘what were the steps?‘”

In a job interview, asking “what are the steps that lead you to your last job?” or “what were the steps that you took toward X achievement?” can help clarify a person’s process. That question can also explain life-changing decisions, which make for great stories.

Regardless of how good your questions are, though, there are some people who “just aren’t very reflective,” says Alex, which means you need to be a little more pointed with your question. In that instance, he recommends asking “if the old you could see the new you, what would they say?

“A lot of times, someone will say something that seems very important to them…you can tell it’s meaningful. And you have no idea what it means — you know that there’s something that they’re getting at, but they’re not articulating it very well. And Ira (Glass, of This American Life) used to use this all the question all the time,” Alex says, “and it’s ‘what do you make of that?'”

By asking someone to probe into what they’ve already told you, you can get their feelings about a subject, as well as more clarity for you as an interviewer.

And finally, there’s a bonus question, which is none at all.

“Shut your mouth,” Chip writes. “Wait. People hate silence and rush to fill it. Ask your question. Let them talk. If you have to, count to 10. Make eye contact, smile, nod, but don’t speak. You’ll be amazed at the riches that follow.”

Alex agrees, noting that often, a subject’s desire to fill the silence can lead to great information.

“I can’t get across enough the importance of shutting up” he says.

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Hanna Brooks Olsen

Hanna Brooks Olsen is a writer and editor for CreativeLive, longtime reporter, and the co-founder of Seattlish. Follow her on Twitter at @mshannabrooks or go to her website for more stuff.