3 Of The Toughest Interview Questions And How To Answer Them

Job interviews can feel a lot like going on blind dates with prospective employers. While there is plenty of advice for how to answer both the most common and the most annoying interview questions, when an interviewer throws a curveball question, even the quickest thinker can get unnerved.

Glassdoor regularly publishes tough questions submitted by users who’ve interviewed at a variety of companies. Now they’ve culled a short list of the most difficult ones based on how users rate them. The list ranges from the highly technical to the just plain unexpected, from questions attempting to draw on the candidate’s knowledge of algebra and geometry, to those trying to discern how well they work with others.

In order to help prepare you if you’re asked questions like these, we asked recruiters to share the best way to answer some of the most challenging ones.

The Culture Question

For the position of production technician at Procter & Gamble, the interviewer asked:

If a coworker had an annoying habit, and it hindered your quality of work, how would you resolve it?

How to answer it. “The best answers to questions about how you would behave include examples from your past,” says career coach Phyllis Mufson. So she advises being prepared with anecdotes that illustrate your skills and judgment. Her reply would be: “I’d make a straightforward, business-like request. For example, in the past, I worked with a coworker who played music when we were working on a deadline. I took her aside and asked her to turn it off, saying that the music was making it hard for me to concentrate. She said that music helps her concentrate. Then I asked for her help. What could she do to make it easier for me to focus and work on deadline? Then she offered to wear headphones.”

Jayne Mattson, senior vice president of Keystone Associates, an executive outplacement and career coaching firm, agrees that when you are asked a hypothetical question, it’s best to answer it with a real example. “The more you share a story of how you handled a situation like this one, the more you will convince the interviewer you could handle this type of coworker now or in the future,” she explains.

However, Mattson says, if you can’t think of a specific situation, you would have to give a “this is what I would do versus what I’ve done” answer. “Before you answer, take a breath and pause to really think,” she advises. Then she would say something like: “I take great pride in the quality of my work, so if one of my coworkers prevented me from doing my best, I would use an honest, direct approach with that person. I would ask my coworker to get a cup of coffee and sit down for a moment in a private place. I would listen to what they had to say, and then work out a solution to where both of us can do our work effectively. I would thank them for being so receptive to my feedback, and mention that if there is something that I do that hinders their work, to please let me know.”

The Technical Question

For a data analyst position at Uber, an interviewer asked:

Write an equation to optimize the marketing spend between Facebook and Twitter campaigns.

How to answer it. Nicolette Cieslak, director of Demand Generation at HighGround, a maker of employee engagement software, took a stab at this question. Initially, Cieslak says that she wondered whether the employer wanted her to demonstrate what she remembers about ninth-grade algebra, or show what she knows about the factors that go into ad performance.

So she came up with an equation, pictured here.

“I’d say the full-on equation is a highly technical question and demonstrates an understanding of all the elements that go into crafting pay-per-click (PPC) campaigns,” says Cieslak, so it definitely demonstrates the person has the expertise to get the job done.

“Another way to answer it may be as simple as x=test(1/0), which is translated to ‘test times infinity,’” Cieslak explains. This response, she points out, “is a bit more provocative in nature as a creative response.” Cieslak says that’s because it not only delivers the equation, but it begs a follow-up question, so it’s most conducive as a conversation starter.

“If someone is taking that response at face value, it may seem too simplistic,” she warns. “But what the response lacks in complexity, it inherently gets to the essential nature of ad buys: That you must always be testing, have an appetite for failure, and motivation for improvement. So this response may tell you more about the person and how they would add value to the organization in the end.”

The Total Curveball

For a data analyst position at Bloomberg, an interviewer posed this question:

How do you explain a vending machine to someone who hasn’t seen or used one before?

How to answer it. Paul McDonald, a senior executive director at global staffing firm Robert Half, first points out that the hiring manager probably wants to know how you think and relate to people with different skill sets. “If you’re interviewing for a tech role,” McDonald says, “the hiring manager wants to gauge how well you communicate with non-technical staff.” As more departments collaborate on projects than ever before, McDonald says your ability to present and interact with various teams is critical.

In your answer, he suggests using descriptive phrases that everyone can relate to. “Avoid being flip or condescending,” he maintains, and tell a story if you can. “These devices are like mini-convenience stores, and allow you to buy snacks, drinks, and more any time of day. Think about the last time you were thirsty, but couldn’t get to the store to buy a drink. If you’re in an airport, office building, or subway station, you’re probably in luck.”

Always Appropriate

McDonald says it’s important to remember that there’s no single correct answer to off-the-wall interview questions, but hiring managers are asking them more frequently. “They want to understand what makes the candidates tick,” he notes, “how they think, and how they respond to the unexpected.”

Hiring managers use them to gauge non-verbal cues that make you look flustered, upset, or nervous, like refusing to answer or using upspeak (i.e., ending the sentence as if you’re asking a question rather than responding). That’s why McDonald advises expecting the unexpected in the interview. “Be flexible, positive, and proactive in your response,” he says. And don’t forget that “it’s fine to ask for a moment to collect your thoughts.”