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SuccessThe Interview Playbook

These are the job interview questions people hate answering—and how to approach them

Orianna Rosa Royle
By
Orianna Rosa Royle
Orianna Rosa Royle
Associate Editor, Success
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Orianna Rosa Royle
By
Orianna Rosa Royle
Orianna Rosa Royle
Associate Editor, Success
Down Arrow Button Icon
March 29, 2023, 11:00 AM ET
Job candidate waiting in reception
According to a recruitment expert, candidates anticipate the most simple interview questions with horror.Koh Sze Kiat—Getty Images
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For many of us, job interviews can be a nerve-inducing experience.

In some situations, that anxiety is exacerbated when a potential employer goes to extreme lengths to find out if prospective new hires are a good match by asking elaborate, difficult, or overly intrusive questions.  

One deeply personal interview question recently went viral on Twitter after being labeled by users as a “new level of job application hell”.

The prospect of being asked something like, “how do you feel life has worked out for you so far?” appeared to be enough to send people into a panic about all the inappropriate questions that could potentially come up while job hunting.

But in reality, according to a recruitment expert, it’s actually the more simple routine interview questions that candidates anticipate with horror.

The five most dreaded interview questions

In an interview with Fortune, Lewis Maleh, CEO of the global executive recruitment agency Bentley Lewis, drew on the 170 years of combined experience at his firm to outline the interview questions job seekers dread most.

1. Tell me about yourself.

Because this question is vague it can leave candidates unsure of how much detail to provide, how personally to answer, or how to answer at all, as the question doesn’t have an obvious structure, Maleh said.

2. Why did you leave your last job? 

Deciding how much detail (and honesty) to reveal can be challenging, Maleh said, especially if you left your last job because you were unhappy or it was not an amicable parting.

3. What do you think of your current or previous boss? 

Similarly, it can be difficult to know much detail to go into if it was not a positive relationship, Maleh told Fortune. 

4. Describe a difficult situation and how you overcame it.

Because this question is somewhat vague, Maleh explained that many jobseekers feel unsure whether to discuss project-based or internal colleague-based challenges if they are unprepared with an example.

5. What are your salary requirements? 

This can be a tricky question to answer if there is no indication in the job ad, if the salary for the role varies between organizations, or if you are looking to earn more as part of your career move but are unsure of the benchmark.

Tips for addressing dreaded interview questions: Take your time

A lot of the panic involved in answering a dreaded interview question isn’t anything to do with the question itself—it’s the stumbling around for an answer and drawing a blank.

It’s why Maleh recommended taking a few moments to think before responding.

“It can be easy to launch straight into an answer without considering your response,” he said. “You appear much more thoughtful by pausing before your answer to think it through.”

One way to give yourself a pause to formulate your answer is by paraphrasing the interviewer’s words at the start of your sentence, giving your brain a head start.

An interviewer is rarely trying to trip you up or trick you—so if you’re racking your brains for an answer but you genuinely didn’t understand what’s being asked from you, Maleh advised asking the interviewer to repeat the question.

“Ask questions of your own if you feel like something is unclear or if you want more information about the topic being discussed,” he added.

Preparation is key

Another useful tip on how to navigate tricky interview questions came from LinkedIn Career Expert Charlotte Davies.

“Most interview questions are essentially the same for a number of roles but just packaged differently,” she told Fortune. It means you can take a lot of the stress out of coming up with an answer from scratch on the spot by having a few generic responses up your sleeve.

By listening to what exactly it is they’re asking from you, you can then adjust one of your rehearsed responses accordingly.

“If interviewees prepare effectively for those key topics—getting to the heart of why the question is being asked and how they can use it to their advantage—they should feel confident walking into any room, ready to tackle whatever is thrown at them,” Davies added.

For example, it’s almost guaranteed that interviewers will ask about your suitability for the role.

So Zahra Amiry, Omnicom Media Group’s associate director of talent attraction, recommends going through the job description “with a fine tooth comb” and dropping the skills set listed in your answer—if you can back it up with evidence.

She suggested using the PEE (point, evidence, explain) method to structure your responses.

“Make your point, provide a brief example of a time when you’ve done this and explain why this was successful,” she advised.  

It could be helpful to rehearse potential responses with your friends, family or a trusted peer so that when it comes to the real deal, you can confidently relay your credentials and competency.  

Plus, it pays to remember that you’re interviewing the employer, just as much as they’re interviewing you.

“Don’t be afraid to check out your interviewers on LinkedIn,” Amiry said. “Knowing who will be sitting on the other side of the table can make the process feel more like an equal exchange and less intimidating.”

Honesty is the best policy

When asked questions around negative scenarios, like why you were fired from your last job, it might be tempting to come up with an embellished or completely fabricated response—but experts advise not to take this route.  

“Be as honest as possible,” Maleh cautioned, but noted that this didn’t mean being outright rude or highly critical of your former workplaces. “If you felt you did not gel with your previous manager or your career progressions weren’t supported, communicate what you are looking for in your next manager or role.”

Davies agreed that many of these classic questions, like “tell us one of your weaknesses” or “describe a difficult situation,” are often asked to gauge self-awareness. 

Her top tip is to “tackle it head on and use it as an opportunity to reverse negative attributes and flip them to be positive.”

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About the Author
Orianna Rosa Royle
By Orianna Rosa RoyleAssociate Editor, Success
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Orianna Rosa Royle is the Success associate editor at Fortune, overseeing careers, leadership, and company culture coverage. She was previously the senior reporter at Management Today, Britain's longest-running publication for CEOs. 

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