How to Answer Challenging Interview Questions

Going into an important interview, you’ve probably prepared your answers for the questions you know are coming.

What would you bring to the company?
Could you tell us about a time you demonstrated leadership?
When can you start?

Easy peasy. But all it takes is one question you’re not ready for, one question that causes you to stumble, to shatter the façade and leave you feeling insecure.

That, of course, is the goal of tough interview questions: to unnerve you. To see how you deal with pressure.

This blog post is intended to prepare you for some of those questions so when they come, you can respond with confidence.

Why should I hire you?

This one seems simple but a lot of people get tongue-tied trying to avoid slipping over the thin line between confidence and cockiness.  Keep it simple. Ultimately, most hiring managers are just asking what makes you special. Whether it’s your aptitude for learning new things, your unique experience, or your desire to prove yourself, you should already know the answer to this question before you submit your application.

Why is there a gap in your work history?

There are a lot of reasons people may take time off from working. Remember that you’re not obligated to share anything personal; if you took time off for health or family reasons, you can say just that and spare the interviewer the details. If you were legitimately struggling to find work, frame it in a more positive light, like, “I was taking my time looking for the right job with the right company.”

What didn’t you like about your last job?

Careful here. You may have a lot of negative feelings about your last company but you should try to keep the interview as positive as possible. It’s ok to be a bit vague here. For example, if you didn’t get along with your boss, you might say that you didn’t feel you were being supported in your goal to advance your career. It’s true but doesn’t imply you might be difficult to work with.

What’s your biggest weakness?

Your interviewer is asking you to be humble here so don’t avoid it. Instead, use this as an opportunity to demonstrate your self-awareness and your commitment to self-improvement. Something like “In the past, I struggled with organization but in my last role, I developed a system that helped me improve tremendously.”

What’s your dream job?

It’s tempting to say, “The one I’m interviewing for!” but that probably isn’t the case. Most likely, you see the job you’re applying for as a stepping stone to the role you’d really like one day. Your hiring manager will be glad to hear you’re ambitious, with your sights set on upward mobility.

How do you deal with difficult coworkers?

Hopefully, you deal with difficult coworkers by maturely working to resolve your differences and bringing in a manager if and when that fails, so you can just say that. Whatever you say, be aware that the interviewer may be trying to determine whether or not you’re the difficult coworker. Don’t give them any reason to think you’re not a good team player.

Tell me about a time you failed at something?

Similar to the question about your biggest weakness, this question is requesting some humility but it’s also looking for some indication of how you accept responsibility and overcome failure. For that reason, don’t choose a situation from your past where your failure could be attributed to sheer luck or someone else’s mistakes. Take responsibility and explain how you grew from the experience.

What concerns do you have about your ability to do this job?

If this sounds like a trick question, that’s because it is. If you express too much self-doubt, you may be removing yourself from the list of potential hires. So don’t go that route. Instead, use this as an opportunity to show your understanding of the company and the role. For example, “I know this position requires a lot of teamwork so I’m looking forward to meeting those I’d be working with most closely to ensure there’s a good fit.”

If you were the CEO of this company, what would you do differently?

Don’t shy away from this one. A lot of companies appreciate feedback from employees on how they can grow and improve so show them that you would be the kind of employee that would share their ideas. You might tell the interviewer about something your last company did that was effective or do not be afraid to share any idea you believe would effectively better the company.