How to Answer the 5 Toughest Job Interview Questions

Prepare for these common, but daunting, interview questions.

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You’ve done your research and found the job that you want to land. Maybe you’ve even cleared the initial phone screening or first interview. But don’t start celebrating just yet; there’s still a long way to go before you can call that position your own. 

As the competition thins but intensifies and the stakes rise, you can count on having to handle some harder interview questions. Tougher, more awkward questions often come in the later rounds.  

Here are five of the toughest questions your interviewers may fire at you – and how to answer them:

1. Tell me about a time you failed. This is one of the most popular and awkward interview questions because it’s so difficult for most people to gracefully discuss failure without worrying that they’ll say something that turns off their prospective employer. Career coach Christie Mims explains that with this question, the interviewer is trying to gauge how you respond under pressure and grow from adversity. Mims suggests that the best way to answer this question is honestly. “Highlight a failure and then follow up with what you learned and how you changed,” she says. “Interviewers are less concerned with the failure than how you handled it (you are human after all). They want to know that you are capable of thoughtful growth and can handle stress under pressure.”

2. Why do you have gaps on your résumé? It’s not unusual to have gaps between periods of work and unemployment – particularly in this economy.  But it’s important to know how to explain any gap (or gaps) appropriately. Mims recommends targeting your answer around how your particular time out of work actually benefits your employer. “A great answer is going to include positive action and an explanation,” she says. “‘I took some time off in between jobs and focused on volunteering on XYZ project/organization, and I’m excited to bring that skill set here,’ instead of finger pointing: ‘My company tanked and the economy is terrible,’ or worse, complete lethargy: ‘Things have been hard recently and I haven’t really found anything.’ Show that even when things get tough, you’ve still got gumption to keep trying.”

3. What is your greatest weakness? Almost every professional interview includes some variation of this question, which doesn’t make it any less awkward to answer. Many experts advise finding a way to turn a negative into a positive – for example, by stating that you work too hard, have perfectionist tendencies, or are too passionate. There’s another possible approach, though, that David Reese, vice president of people and culture at Medallia, recommends: being honest. “Many interviewers are not really looking to find out whether a candidate’s organizational skills could use improvement, or that they struggle with presenting to large groups or even leading large teams,” he says. “They’re trying to find out whether they have self-awareness, whether they are able to be critical and most importantly, whether they’re able to tell the truth – when it’s difficult.”

4. Why did you leave your last job? A variation of this question is, “Why would you consider leaving your current job?” What’s tough is that this straightforward-seeming question can become a minefield if you’re not careful about the tone of your response, so you need to walk a fine line when answering. 

“If you left or will leave because you don’t feel that you can go any farther up the ladder there (because your manager is not interested in your development or the organization is limited in what it can offer), you want to convey this in an upbeat way,” says Anna Ranieri, an executive coach. “This should sound something like, ‘I learned a lot at ABC Inc., and contributed a lot to my department and the company. I feel that I've gone as far as I can go there and it’s time to take my next step. I know that I can do more and contribute more and continue to learn in an environment like yours.’”

5. Don’t you feel like you’re overqualified for this job? In a job market that’s been down-in-the-dumps for an extended period, many job seekers will be clearly overqualified for certain jobs to which they apply. The key to answering this question appropriately is to get inside the mind of hiring managers, who may fear that their organization may be left in the lurch if you leave in short order for a higher-level position. 

Ranieri advises turning the tables and promoting the positive features of your over-the-top skills or experience. “You can say: ‘Here are the skills that I can bring to the position that will allow me to contribute more than the job description requires. I think that will be to everyone’s benefit right away,’” she suggests. “Or you can say: ‘I'd be very pleased to join your group in order to become part of this enterprise that I respect. I’ll work hard from the start, be resourceful and creative, and will enjoy this role. I believe that I can continue to evolve with the organization and eventually grow into whatever role would come next.”