Career Advice, Interviews

10 Toughest Job Interview Questions — And How to Answer Successfully

We’ve all been there—pleased that an interview was going really well until the interviewer threw out a real doozy of a question that you just don’t know how to answer. But you don’t have to panic. We asked career coach Hallie Crawford to give us advice on how to answer the most difficult questions you’ve ever been asked. (Yes, we pulled them from real interviews.) Here’s how to answer each really well.

1. If your current employer had an anniversary party for you, what five words would be written on the cake to describe you?

While it may seem silly, “this question is designed to reveal how you think your manager perceives you,” Crawford says. “Before answering, ask yourself: how do your coworkers describe you? What did your manager commend you on recently?” With the answers to these questions in mind, “don’t be afraid to get a little creative with your reply,” Crawford says. But don’t be too verbose either. “You don’t want to give the impression that your anniversary cake would be too big,” she says, “so try and keep the words short and sweet.”

2. Who in history would you want to go to dinner with and why?

Before you answer this one, ask yourself whom you admire, past and present. “Perhaps a writer, an actor, a scientist, or even someone from your industry,” suggests Crawford. Then, consider, “what do you appreciate about their accomplishments? Why do they inspire you? Why do you feel that you would be friends? What would you want to discuss with them at dinner?” Crawford prompts you to ask yourself. “Use these elements when answering.”

3. Name a brand that represents you as a person.

Yep, not a brand you love—but one that embodies who you are. Now that’s a doozy. But it doesn’t have to be tough, Crawford says. “Think about your top personal values,” Crawford advises. “Now think about brands that also have those values. For example, if you value family and ethical practice, think about companies who are family-based, or create products for families who you know don’t do testing on animals, for example. Explain the values that you feel you share with the brand and why those values are important to you.”

4. Please describe an instance where you had to make a decision without all of the necessary information.

You came to the interview prepared, which means you have a list of accomplishments you can work from. Using an accomplishment for this question, “describe the situation and what information was missing and any measurable results achieved,” Crawford instructs. By using an accomplishment, you will show a hiring manager how you can persevere.

5. Sell me on one idea, and then sell me on the opposite of that idea.

“First of all, you want to think of an idea before you can start answering the question,” says Crawford. You may not have to come up with your own idea. “Ask the hiring manager if they have a specific idea in mind,” says Crawford. “If not, consider a recent idea that you discussed with your team or with coworkers. What was your position and why? What was the opposite position and why? Use those arguments. In this question, it is important that you sound convincing when presenting both ideas. This will provide insight into whether you are able to present ideas to your team—even if you don’t agree with the idea.”

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

This may seem like a perplexing question, but it’s “designed to get to you how you deal with others,” explains Crawford. “Draw from a real-life experience if possible. What annoyed you? How did you resolve it? Is there a more effective way to handle the situation if it would happen again? Identify the annoying habit and then outline the steps you would take to try and resolve the situation while maintaining a good relationship with your coworker.”

7. What part of the newspaper do you read first? What does this say about you?

“This kind of question is asked to get to know you better as a person,” says Crawford. And while “at first glance, this seems a fairly easy question,” she says, it’s not. So, “before you answer, think about what genre of articles appeals to you: technology, fashion, current events,” Crawford advises. “Now determine if there is a way to link the genre that appeals to you as a professional. For example, if you are drawn to articles about technology, you could explain that your love of technology means that you enjoy learning new ways of doing things, you are open to change, and look to stay on top of current trends.”

8. Throw your resume aside and tell me what makes you you.

This is another question designed not to trip you up, Crawford says, but to get to know you better. “Keep in mind that they may have looked you up online and have your cover letter, so do your best not to just repeat something they have already read about you,” she says. “Instead, is there a background story about how you got into your industry? Can you explain your unique selling proposition—why you are unique in your industry? Or, you could explain your top three values and why they are important to you.”

9. What’s wrong with your past or current employer?

At all costs, “remember that you want to avoid bashing your current or past employer and the company,” warns Crawford. “This question is designed to find out why you are looking for a new job. Instead of focusing on them, focus on you. Are you looking for more career growth that what is offered where you currently work? Or a more challenging position?”

10. Tell me about the worst manager you ever had.

Before you bash your last boss, “remember that your hiring manager has your resume and knows where you have worked, so your managers won’t be completely anonymous,” warns Crawford. “However, you might explain a type of management style that wasn’t ideal for you. And if you haven’t had a bad manager, don’t make one up. Let the hiring manager know that you honestly have gotten along with your previous managers, and focus on how you are able to work with different personality and management styles.”

 

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