Why Are Manholes Round? The 10 Toughest Interview Questions

A job interview at one of Google’s 75 campuses around the globe might seem to have more in common with pledging a secret fraternity than job-hunting. An often months-long interview process, iron-clad non-disclosure agreements and back-to-back hours of interrogation in windowless offices are a matter of course, but the added intrigue of allegedly absurd interview questions takes the experience into cloak-and-dagger territory.

Why are manhole covers round? How do you measure 4 gallons of water using only a 3 and 5 gallon jug? How many gas stations/dogs/windowpanes are there in the United States? According to career communityGlassdoor.com, these are a few of the more obscure queries asked of wannabe Googlers.

You have to give it to them, the questions are creative. But are they effective in finding the right candidate? And more importantly, will answering them correctly land you a job?

“This kind of question is used to determine poise and the ability to think on one’s feet,” says Dale Austin, director of career services at Michigan’s Hope College. “But also to assess creativity and problem-solving.” In other words, Google is looking for a quick answer that proves you’re not only agile but logical, adaptable and math-minded.

That’s all well and good for the analytical minds of Googlers, but veteran Bay-area executive headhunterChuck Pappalardo says it really all depends on what you’re looking for. For Google, whose ranks Pappalardo describes as “engineer from top to bottom,” they can prove telling. “These kinds of questions measure whether someone can work in the crazy environment [of a young tech firm] and have the right engineering background to make them a good employee. They show quick, analytical thinking, and the ability to pivot.”

But what these “trick” questions can’t highlight is a quality that Pappalardo sees as not only more human, but more vital to the majority of careers–positions where customer or client interaction is essential. That quality? Integrity.

“A good interview requires more than just good questions. It also requires a deep understanding of the traits and behaviors you’re seeking or avoiding,” he says. “By crafting questions designed to elicit “evidence” of the desired characteristics, you’re able to draw conclusions about candidates’ ability to perform in an authentic and meaningful way.”

Fine, if you’re on the questioning side of the desk. But for those of us in the hot seat, prepping for questions designed to “elicit characteristics” can be quite tricky. Pappalardo concedes they can be among the most difficult to answer, because they require much more than rattling off resume points. Here, the 10 toughest—but most telling– interview questions, and best of all…how to answer them.

1. Why is there a gap in your work history?

“Employers understand that people lose their jobs and it’s not always easy to find a new one fast,” says Susan Nethery, the director of student affairs marketing at Texas Christian University, who often advises recent grads on the interview process. When answering this question, list activities you’ve been doing during any period of unemployment. Freelance projects, volunteer work or taking care of family members all let the interviewer know that time off was spent productively.

2. Can you think of a recent problem in which old solutions wouldn’t work?

This question is seeking a creative answer. The interviewer is trying to identify how knowledgeable you are in today’s work place and what new creative ideas you have to solving problems. Ex: Your workplace swears by fax machines for signing contracts. Until the phone lines go down. Did you save the day with a scanner and an emailable .pdf? You may want to explore new technology or methods within your industry to be prepared for. Twitter-phobes, get tweeting. Stat.

3. What would the person who likes you least in the world say about you?

“The people who can’t answer this question are the people I worry most about,” says Jim Link, managing director of human resources at staffing firmRandstad. “I can honestly say I’ve never hired one of them.”

Link says that this tricky question, a twist on the “what’s your worst quality or weakness?” standby, often leads to pregnant pauses as the interviewee struggles to present an answer that won’t present them in a bad light. “I’m not saying answer it quickly, because you should definitely answer it thoroughly.” Highlight an aspect of your personality that could initially seem negative, but is ultimately a positive.  His example? Patience—or lack of it. “Used incorrectly this can be bad in a workplace. But always driving home deadlines can build your esteem as a leader.”

4. What is the biggest risk you’ve ever taken?

“Some roles require a high degree of tenacity and the ability to pick yourself up after getting knocked down,” says Dale Austin, director of career services at Michigan’s Hope College. Providing examples of your willingness to take risks is important because it not only shows your ability to fail and rebound, but also your ability to make risky or controversial moves that succeed.

5. Have you ever had a supervisor challenge your behavior? How, and how did you manage that?

Pappalardo shares an anecdote from an interview he recently conducted. “The head of IT was rolling out a new technology to the sales team that required two days of training. He wouldn’t back down despite sales pushing back saying they couldn’t make time for it. Finally the president of the company challenged him about his actions, forced him to rethink his stance. He was a senior executive standing on propriety, not creativity.” In the end, Pappalardo says the executive rebounded and a compromise was reached—but it’s the lesson learned, not the situation, that the interviewer is looking for.

6. Describe a time when you were part of a project or planning team that could not agree…

Lynne Sarikas, director of the career center atNortheastern University’s business school, stresses that questions pertaining to difficulties in the past are a way for potential employers to anticipate your future behavior “by understanding how you behaved in the past and what you learned.” It’s important to clarify the situation succinctly, she says, to explain what specific action you took to come to a consensus with the group and describe the result of that action.

7. If you could change one thing about your last job, what would it be?

Beware oversharing or making disparaging comments about former coworkers or supervisors, as you never know what bridges you may be burning. But Taylor warns that an additional trouble point in answering this query is showing yourself to be someone who can’t vocalize their problems as soon as they arise. A good rule, she says, is to steer clear of people. Problems with technology are safe ground.

8. Explain a database in three sentences to your 8-year-old nephew.

This frequent Google question is no trick, and Taylor says it can be tailored to any sector. “Explainingpublic relations, explaining mortgages, explaining just about anything in terms an 8-year-old can understand shows the interviewer you have solid and adaptable understanding of what it is they do.” Do your homework, she says, “Know the industry and be well-versed.”

9. Tell me about yourself…

Seems simple, right?

It’s not. “This is difficult because people tend to meander through their whole resumes and mention personal or irrelevant information in answering,” says Dawn Chandler, professor of management at Cal Polytech’s business arm. Jana Fallon, a VP of staffing and recruitment for Prudential, agrees. “Keep your answer to a minute or two at most. Cover four topics: early years, education, work history, and recent career experience. Emphasize this last subject. Remember that this is likely to be a warm-up question. Don’t waste your best points on it.  Keep to your professional career!  (e.g., don’t cover your family life, weekend activities, pets, collections, etc.)

10. Why should we hire you?

The most overlooked question—and also the one most candidates are unprepared to answer. Chandler suggests that this is often because job applicants don’t do their homework on the position, and as a result aren’t able to pinpoint their own unique qualifications for the job. What they are really asking is why you are more qualified than everyone else. “You need to review the job description and qualifications very closely to identify the skills and knowledge that are critical to the position,” she says, “and then identify experiences from your past that demonstrate those skills and knowledge.”

5 Ways To Spot A Bad Boss In An Interview

A boss can literally, make or break your career. Here are five ways to spot the bad ones before they become yours.

A great boss can make you feel engaged and empowered at work, will keep you out of unnecessary office politics, and can identify and grow your strengths. But a bad boss can make the most impressive job on paper (and salary) quickly unbearable. Not only will a bad boss make you dislike at least 80% of your week, your relationships might suffer, too. A recent study conducted at Baylor University found that stress and tension caused by an abusive boss “affects the marital relationship and subsequently, the employee’s entire family.” Supervisor abuse isn’t always as blatant as a screaming temper tantrum; it can include taking personal anger out on you for no reason, dismissing your ideas in a meeting, or simply, being rude and critical of your work, while offering no constructive ways to improve it.  Whatever the exhibition of bad boss behavior, your work and personal life will suffer. Merideth Ferguson, PH.D., co-author of the study and assistant professor of management and entrepreneurship at Baylor explains that “it may be that as supervisor abuse heightens tension in the relationship, the employee is less motivated or able to engage in positive interactions with the partner and other family members.”

There are many ways to try and combat the effects of a bad boss, including confronting him or her directly to work towards a productive solution, suggesting that you report to another supervisor, or soliciting the help of human resources.  But none of those tactics gurantee improvement, and quite often, they’ll lead to more stress. The best solution is to spot a bad boss—before they become yours! Here are five ways to tell whether your interviewer is a future bad boss.

1. Pronoun usage. Performance consultant John Brubaker says that the top verbal tell a boss gives is in pronoun choice and the context it is used. If your interviewer uses the term “you” in communicating negative information ( such as, “you will deal with a lot of ambiguity”), don’t expect the boss to be a mentor.  If the boss chooses the word “I” to describe the department’s success—that’s a red flag.  If the interviewer says “we” in regards to a particular challenge the team or company faced, it may indicate that he or she deflects responsibility and places blame.

2. Concern with your hobbies. There is a fine line between genuine relationship building, and fishing for information, so use your discretion on this one. If you have an overall good impression of the potential boss it may be that he or she is truly interested in the fact that you are heavily involved in charity work, and is simply getting to know you. On the other hand, the interviewer may be trying to determine whether you have too many commitments outside of work. The interviewer can’t legally ask if you are married, or have kids, so digging into your personal life can be a clever way to understand just how available you are.

3. They’re distracted. The era of email, BlackBerrys and smartphones have made it “okay” for people to develop disrespectful communication habits in the name of work. Particularly in a frenzied workplace, reading email while a person is speaking, multi-tasking on conference calls and checking the message behind that blinking BlackBerry mid-conversation has become the norm of business communications. But, regardless of his or her role in the company, the interviewer should be striving to make a good impression—which includes shutting down tech tools to give you undivided attention. If your interviewer is glancing at emails while you’re speaking, taking phone calls, or late to the interview, don’t expect a boss who will make time for you.

4. They can’t give you a straight answer. Caren Goldberg, Ph.D. is an HR professor at the Kogod School of Business at American University. She says a key “tell” is vague answers to your questions. Listen for pauses, awkwardness, or overly-generic responses when you inquire what happened to the person who held the position you are interviewing for, and/or what has created the need to hire. (For example, if you are told the person was a “bad fit,” it may indicate that the workplace doesn’t spend much time on employee-development, and blames them when things don’t work out).

You should also question turnover rates, how long people stay in given roles, and what their career path has been. All of these answers can indicate not only if the boss is one people want to work for, but whether pay is competitive, and employees are given a career growth plan.

5. They’ve got a record. Ask the potential boss how long he or she has been at the company, in the role, and where he or she worked before coming to it to get a feel for his or management style, and whether it’s what you respond to.  For example, bosses making a switch from a large corporation to a small company may lead with formality. On the other hand, entrepreneurs tend to be passionately involved in business, which can be a help or a hindrance, depending on your workstyle.

Goldberg also recommends searching the site eBossWatch, where you read reviews that former employees have given to a boss. If you’re serious about the position, she also suggests reaching to the former employee whose spot you are interviewing for, and asking for their take on the workplace. (LinkedIn makes this task easy to do). The former employee’s recount may not necessarily reflect your potential experience, but it can help you to determine whether his or her description of the job and company “jibes” with what the potential boss said.