6 Grueling Job-Interview Questions To Get Through

Recruiters are creating new quandaries for candidates as well as with using some old standbys more frequently. How to prepare for them. 

Why don’t you tell me about yourself?

What are your weaknesses?

Where do you see yourself in five years?

Those three questions, along with a couple of others, are perennially the toughest any job candidate will be asked. They’re designed to give a potential employer a sense of the candidate’s personality, ambition, self-awareness, and agility—all crucial things to know before extending a job offer.

But these days, talent professionals are throwing a couple of curveballs at candidates. Career coaches and hiring managers say that the post-pandemic work environment has made organizations more aware of the traits they need in new recruits, as well as of how the usual tough questions haven’t been eliciting those traits. “There are a lot of questions now around resiliency and stress,” says Stacey Perkins, a career coach for Korn Ferry Advance.

As with all job-interview questions, you can prepare for these new ones (or for the old ones that have been popping up more frequently lately).

What are your thoughts on working remotely?

Eighty-eight percent of companies say they are mandating that employees work a certain number of days on-site, up nearly 20% since 2022, according to a recent survey by workspace scheduling firm Robin. If candidates flat-out refuse to work in an office, experts say, they should be aware that they may be taking themselves out of the running for some jobs.

More importantly, however, this question is designed to elicit answers about how candidates can collaborate and work effectively when they are not in the office. “Employers want to know that you will make the effort to collaborate,” Perkins says.

What do you do when you make a mistake?

“At the end of the day we’re all going to make mistakes,” Perkins says. This question (or its cousin, “Tell me about a time you failed”) seeks to find out how a candidate handles stress. Employers want to know whether a candidate holds themself accountable for errors and how they bounce back from failure.

What do you do outside of work?

It might seem like none of an employer’s business. But Perkins says some employers ask this question to find out about the balance a candidate has in their life. Employers are leery of workers burning out, since wiped-out employees are often unproductive ones. If this question comes up in an interview, it’s fine to talk about hobbies, family, volunteer work, or anything else that keeps you happy.

Why is there a large time gap in your résumé?

Employers are usually pretty forgiving about long gaps in job histories during bad economic periods. For example, few employers will hold it against a candidate if they were unemployed during the lockdowns in 2020, or, going back further, the Great Recession of 2008-2009.

But if there’s a big gap during the robust job market of the past three years, some recruiters may get more circumspect. In these cases, candidates should be prepared to discuss not why they couldn’t find a job, but also what exactly kept them from getting one. (Perhaps they had to care for a dependent or needed to hone certain professional skills.)

What did you do during the Great Resignation?

These days, employers seem warier of people who’ve held multiple jobs within a short timeframe than they are of someone who couldn’t find a job for several months or even years. That could pose a problem for the millions of people who changed jobs during 2021 and 2022, when many employers were throwing around big signing bonuses and other perks to attract talent. “A bunch are having a hard time explaining their job moves,” says Brittney Molitor, a Korn Ferry managing consultant who places human-resources professionals.

The best way to answer this question, experts say, is to be honest. If a candidate made a move for purely financial reasons, they should just say so. They should then explain why they’re looking for a new position now.

What do you do when you disagree with your manager’s decision?

It’s rare that someone agrees with every decision their manager makes. And these days, there are plenty of issues on which a subordinate and their manager might disagree, from flexible work scheduling to promotion decisions to business strategy. Experts say recruiters increasingly are asking about these disagreements. “It’s not only important to show you stood up for yourself, but also how you did it,” Perkins says.

This question can also be used to determine how well a candidate handles tough feedback. Recruiters want to know about experiences in which a candidate accepted criticism and improved their work.


For more expert career advice, connect with a career coach at Korn Ferry Advance.