5 Interview Questions You Should (and Shouldn’t) Ask

I’ve had my lion’s share of job interviews. Most good, others not so much. Like the time when the CMO I was meeting with opened his mouth and quashed my desire to write the content for the company’s website.

“If I said ‘Could you start right here, RIGHT NOW, could you?” he barked as he paced back and forth. If his gruff demeanor offered a glimpse into the company’s culture, I wanted no part of it. Besides, how painfully unoriginal was his opening question?

The best interview questions inspire conversation rather than slow it – or as in my case - shut it down. And they shouldn’t be cringe-worthy clichés like “Where do you see yourself in the next 5 years?” Try asking the opposite for a change: “Where do you not see yourself in the next 5 years?” Now there’s a question. Not only is this more original to the ears of the interviewee, but also more enjoyable for the person asking.

“Nobody wants to be asked the same question over and over,” says Ashleah Shelan, a recruiter for Onward Search. “It’s boring and monotonous for everyone. And you know what? These less-common questions make it more exciting for me as a recruiter. I love hearing the responses; it’s exciting hearing people speak about their passion.”

With this in mind, we put together the following list of the more original questions to ask in order to really get to know a candidate.

INSTEAD OF: What would you say your weaknesses are?

ASK THIS: What job would make you want to get out of bed in the morning?

Such a “weak” question was posed to a friend of mine who now works as a neurogenetics researcher in the UK. “Tell me your faults, both professional and personal,” said the interviewer. My Brit buddy’s response: “At this point I realized I didn't want the job so I said ‘I’m overweight, I bite my fingernails, and I leave the seat up when I go [to the loo].’ ”

Laying your flaws bare to someone you’ve just met just seems plain wrong - even offensive. It reminds me of a recurring dream in which I’m walking down the main hall of my high school, completely naked and no one helping me cover up.

Instead, ask questions that are likely to elicit what makes the aspiring employee tick rather than what might make them feel awkward. “I have had many candidates say ‘I like that question,’ ” says Shelan. “They really start to reflect on what it is that gets them excited – and really paint a picture for you of what that looks like.”

INSTEAD OF: Why do you want to work for this company?

ASK THIS: What would you like to do next in your career?

Shout out to Neelu Jain of The Creative Group for this golden nugget. “It’s open ended and doesn’t assume they want to do the same thing,” she says. It’s also a more thoughtful question and therefore more likely to get the candidate to open up. A candidate is likely to speak more freely and extensively about their career than they would about the company.

Here’s a thought: lay both of these questions on the table, written out on pieces of paper, and see which one the aspiring employee chooses. My money’s on the “career” question.

INSTEAD OF: How do you see yourself progressing on this career path?

ASK THIS: If you could explore a different career for a year, what would it be?

Thank you, Kate Gilman of 24 Seven, for this gem. It’s so intriguing to me I imagined how I would answer it.

I would love to go to music school and train to become a professional pianist. Maybe I’d starve but maybe not. Street musicians make bank!

OK, let’s extract what the interviewer learned about me by that single response.

1. That my fingers like to dance across piano keys as well as computer keys.
2. That I have a life outside of my work.
3. That I’m likeable and have a fun sense of humor.

A lot, right? Now let’s imagine if I was asked the career path question.

Interviewer: How do you see yourself progressing on this career path?

Me: [Crickets … then stammering … then more crickets before squeaking out an unconvincing answer.]

See how much more enjoyable it is to not ask (and be asked) the same dull interview questions?

INSTEAD OF: What do you want to do in your next position?

ASK THIS: What’s a project you worked on recently that you’re most proud of?

Shelan says by simply inviting the candidate to talk about their projects, you learn much more about them beyond the work itself. “You can really get a sense of what they are looking for and what they are really passionate about - especially when they are describing a project. They tend to go over this in length and what it was that they enjoyed so much about it. Then you can see where their strengths lie, too.”

INSTEAD OF: Why did you leave your last job?

ASK THIS: What do you like to do on the weekends?

The weekend. Synonymous with fun, leisure and relaxation, it’s bound to loosen up the conversation. How candidates spend time away from the office can reveal as much as when they’re in it.

“It’s a good test to ask about favorite foods and restaurants,” offers Gilman. “It kind of catches them off guard. You can see how they react, but also see if they have good taste.”

The takeaway: don't just stick to the expected interview questions. They don't help you get to know the candidate on the level you would like. Not to mention, the candidate doesn't enjoy answering them (who does?). Mix things up and make yourself and your company stand out.

*image by Justin Brown