5 challenging interview questions to prepare for

June 7, 2023 3:54 PM

As graduates dive deeper into the job search, they may find themselves faced with the same difficult interview questions, to which they give the same vague, uncertain answers. However, with the right preparation, the dreaded interview stage (or likely stages) can feel more like an achievement than a test.

Flexjobs, a remote jobs search engine, collected 30 of the most common interview questions, pulling from sites like Glassdoor, where former employees mentioned what kinds of questions they were asked as candidates. With the help of Flexjobs career expert Keith Spencer, EBN has narrowed it down to the top five most challenging questions candidates can expect at their next interview.

And while there isn't a one-size-fits-all-answer, preparation can look similar regardless of company or industry, underlines Spencer.

"Make sure you know the job description backwards and forwards and that you've done some research on the company," he says. "Regardless of the question, you should try to relate everything back to the employer and the role."

Even if candidates do get stumped and offer what they feel is an incomplete response, Spencer advises them to readdress the question briefly in their thank-you email to their interviewers. By offering to clarify their response, it shows that the candidate is thoughtful and cares about the opportunity, explains Spencer.

Still, it's crucial job hunters consider how to answer certain questions on the spot, especially if they are bound to come up at every interview. Here are the five challenging interview questions candidates can prepare for.

Can you tell me more about yourself?

This is often one of the first questions an interviewer will ask, presenting the candidate with the opportunity to give insights into who they areas a person and new hire.

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"'Tell me about yourself' is often one of the most difficult questions," says Spencer. "People struggle to figure out a relevant response."

Spencer advises candidates to share experiences that underscore why they are qualified for the role. This may mean highlighting their degree and internship experience or even discussing side hustles or recently gained skills in their field.

What is your greatest weakness?

While candidates may be prepared to list off their strengths, they rarely want to highlight their weaknesses — but an interviewer will likely ask anyway in an attempt to measure how self-aware the candidate is.

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The key is to be honest about where one may struggle or lack confidence, but show a willingness to grow and learn, says Spencer. For example, if a candidate shares that they sometimes struggle with multitasking, they should also share what exercises and routines they create for themselves to improve on that weakness, such as breaking up their daily goals each morning and using a planner to keep them accountable.

What would you do in your first 90 days in this role?

This question can be intimidating, especially if the candidate doesn't have direct experience in the role they are applying for. Spencer notes that interviewers likely are seeing how well the candidate understands the role and can plan accordingly.

"Think about the job description, and consider what you want to learn first," says Spencer. "Who would you want to set up meetings with? What looks like the most essential thing to tackle first?"

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Ultimately, it's a hypothetical question that doesn't necessarily have a right answer, but the response should showcase an understanding of what personnel or teams the new hire would connect with, what company projects are relevant to the role and what the candidate may need to learn on the job.

Why do you want to work remotely?

While there are countless reasons why candidates may want to be remote — from cutting their commute, taking care of chores at home and saving money on food and transportation — Spencer asks candidates to focus on why remote work makes them a more effective employee.

"I've had a few remote jobs myself, and that question always comes up," he says. "I know I'm the type of person who gets distracted in the office and I have a dedicated workspace at home where I can be my most productive self. Share something that you know is beneficial to the employer."

What is your expected salary?

Spencer admits that this may be the most awkward question for candidates, but it's a big one.

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"If you're not comfortable with an exact number, offer a range based on current hiring trends, the market value for this type of role and the cost of living in your area," says Spencer. "That way you're not worried you will say something unrealistically high or too low. Do your research."

In addition to offering up some numbers, candidates should express an interest in learning more about the role and benefits at the company. The right benefits may supersede a less exciting compensation offer. Don't be afraid to ask questions, and understand what other areas of value this role may have. says Spencer.