The worst, most nefarious interview questions (and how to answer them)

It doesn’t matter how many tennis balls you think might fit into a limousine, but your problem-solving skills will be carefully examined. Mind these expert tips for acing your next interview.

Difficult interview questions

How many quills would you say an average porcupine has?

Explain “the cloud” to me.

Are you pregnant now, or do you plan on becoming pregnant anytime soon?

These are very bad, no-good interview questions that could unsettle even the most unflappable applicant. How would you respond to such nonsense? How should you respond to such nonsense?

(Editor’s note: Healthy porcupines have about 30,000 quills, give or take, just in case some sadist ever throws that one at you.) recently surveyed 2,000 U.S. residents to determine the worst questions job seekers have ever encountered in the wild. These doozies will make you cringe, but they’ll also make you more prepared for the types of creative curveballs certain recruiters like to throw. found that the most difficult interview question to answer is: “How many gas stations are there in the United States?” That jarring non-sequitur was followed by irritating classics such as, “What’s your biggest weakness?” and “Where do you see yourself in five years?”

In addition to compiling top questions that make job seekers squirm, wince or panic, also found that:

  • Women are more likely than men to be asked why they should be hired and where they see themselves in five years.
  • A quarter of interviewees (25%) have been asked about their personal relationships, and another quarter have been asked about their experiences with police and law enforcement.
  • You are 18% less likely to be asked an illegal question at a job interview in the Midwest region (yer dern tootin’ dontcha know!).

How gender sways and skews questioning’s data reveals that women are more likely to be asked about their perceived strengths, weaknesses and plans for the future. They are subjected to more scrutiny in terms of proving competency, compensation levels and commitment to work—and the questions they tend to receive in the interview process bear this out.

It’s unlawful for employers to directly ask women about maternity plans or pregnancy status. However, many try to circumvent this law by asking the “Where do you see yourself in five years?” question to gauge long-term commitment.

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Men, meanwhile, are more likely to be peppered with questions about politics, religion and brushes with the law.

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Answering thorny questions suggests smart responses to tough questions, including:

“How many gas stations are there in the U.S.?”: Interview coach Pamela Skillings says that interviewers ask these sorts of oddball questions to see how you problem-solve in real time—and under pressure. If you get the gas station question, be ready to perform some basic math and sound out your reasoning. For instance, you can fairly estimate there are about 4,000 gas stations in each state, and multiply that by 50. (The same principle applies for any variation of the “tennis balls in a limo” or “windows in Wyoming” question.)

“You have one minute to persuade me to buy this pen. Go!”: cites the advice of Jordan Belfort, who says to put the pressure back onto the interview. Saying “Tell me, how long have you been in the market for a pen?” or some similar phrase enables you to control and steer the conversation.

“What is your biggest weakness?”:  If you get this old chestnut, bring up an ancillary weakness that you’ve somehow tried to improve. lists “delegation” as one possible response, with a caveat of “so I signed up for a management skills training course.” Use this question as way to demonstrate your commitment toward growth, learning and development.

Read the rest of’s research for more guidance on responding to difficult (or illegal) interview questions.

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