How to answer tough interview questions: What's the biggest challenge you face in your current position?

It's our third week of interview month here at Hollywood Resumes! Don't forget, you can put these strategies into practice by taking advantage of our mock interview service.

Question: Whats the biggest challenge you face in your current position?

We’ve discussed how to answer the “What’s your biggest weakness?” interview question, but another similar question -- and arguably, more popular and trickier -- is “What’s the biggest challenge you face in your current position?” Be careful as you answer this one – there are several slip-ups that are easy to make.

First, let’s think about why you’re being asked this question. There are three main qualities that your interviewer is trying to assess here:

a) How well do you handle difficult or high-pressure situations?

b) Will the responsibilities of the position you’re applying for be too far out of your comfort zone?

c) Can you speak about your current position with poise and professionalism?

With these three questions in mind, you can begin to prepare a “biggest challenge” story that will assure the interviewer you won’t get overwhelmed by difficult situations, you have the primary skills the employer is looking for, and you’ll represent your new company in a positive light.

For starters, you'll want to offer an answer that sounds legitimately challenging and doesn't give away personal information about your current employer (Read: Don't say “my boss changes his lunch order at the last minute every day.”). More importantly, your answer should show you know how to work through any type of problem that arises. Think of something that will allow you to highlight one of your best qualities while you describe the challenge and how you typically deal with it. For example, let’s say you’re an assistant to an incredibly busy boss – multiple phone lines ringing all day long and a schedule that shifts constantly. This is obviously a challenge that forces you to be on your A-game every time you come to work. Communicate this to your interviewer and explain what type of organizational system you’ve created that allows you to manage the situation. This will demonstrate that you can remain level-headed under difficult circumstances and that you’re a problem-solver.

However, choose wisely when deciding on a challenge to describe – if your actual biggest challenge is something you’re still struggling with, and you have yet to come up with a solution to your problem, find a different challenge. You don’t want to disqualify yourself from a position because you have a hard time at your current job with something that you’ll be facing in the new position as well. You wouldn’t want to say, “Well, I assist three different executives, and it’s really hard to manage all their personalities” when you’re applying for a job where you’ll be covering multiple desks (or even the desk of one difficult boss).

Speaking of difficult bosses, you should NEVER bash your current boss during a job interview. Maybe dealing with a boss who regularly screams and throws things at you is your biggest challenge at your current position, but you should not reveal this during your interview – think of a different answer to the question. If the job posting asks for a “thick-skinned” individual, you can get this across in a way that doesn’t necessitate speaking negatively of your current employer – you could simply say that it’s a demanding position in a fast-paced environment. And be aware that sometimes your current boss will have a reputation, and the interviewer might try to coax a negative answer out of you (he might even know your current boss). Just remember – it’s a trap! If the hiring manager hears you complain about your current company or reveal confidential information, he’s going to assume that you’re untrustworthy and will probably be similarly loose-lipped if you’re not 100% happy in your new position. As tempting as it may be to share your most ridiculous assistant horror story, keep it to yourself. Again, you can acknowledge that it’s a demanding desk (and describe how you deal with these demands!), but always remain professional.

--Angela Silak & Cindy Kaplan