How to answer the "toughest challenge" question in your Hollywood interview

Most job interviews will have some version of the question: Whats the biggest challenge you faced in your current position?

Your instinct might be to scream, "Nothing as challenging as this question!" It really can feel like a doozy. You want to answer the question honestly, but also not show too much weakness, or give away too many negative feelings about something (or someone) that might have been problematic at work, and at the same time, you want to show that you will be up for any challenge in this potential new role without being too cocky about your skills.

Skilled interviewers can also tell who has prepared for this question and who hasn't. We don't share that with you to add to your stress, but rather to reinforce the deep need to prepare. By preparing, you're also showing that you're the sort of person who takes yourself and your work seriously and that you're conscientious. 

The first step to preparing an answer for this question is to consider why it's being asked. There are three main qualities that your interviewer is trying to assess here:

1. How well do you handle difficult or high-pressure situations?
2. Will the responsibilities of the position you’re applying for be too far out of your comfort zone?
3. Can you speak about your current (or most recent) position with poise and professionalism?

The second step is to figure out an anecdote that you can share. This is important for all interview questions, but especially here. The interviewer really wants you to be specific, so saying, "Well, we often had a lot of tight turnarounds on set, so that was challenging, but I made sure to work with the AD to keep everything on schedule" isn't going to cut it. 

The anecdote should be a situation that sounds legitimately challenging and doesn't give away personal information about your current employer or proprietary information about a project. For example, maybe the following is true: "I worked on SHOW X, and our budgets were only $150K an episode, and the producers above me were insisting I book CELEBRITY A whose going rate is $80K, and there was no way to get it done with the rest of the show budget, so I had to come up with 50 other pitches of affordable celebrities while my boss screamed at me for being an incompetent fool." But you don't want to say all that, as it includes protected information and a lot of bitterness, and your interviewer might know the producer you're talking about directly -- this isn't the time for gossip or therapy. See if you can figure out a way to share that story without the details or bitterness, or pick a different story that's challenging for reasons that have less to do with mismanagement.

The story should offer an opportunity for you to show how you work through problems, what you learned, and what skills you developed as a result. For example, let’s say your company received an RFP from a coveted client, but your boss was on her honeymoon and you had to fill in to lead the team at the last minute, knowing that you needed to land this contract or your boss would come back upset, and that you absolutely couldn't bother her during her time away. You can talk through your ability to learn quickly, how you used your client services skills to cover for your boss so the potential client wouldn't think they were getting the short end of the stick, how you tapped into leadership skills by rallying junior members of the team to brainstorm awesome ideas, and leaned into your creative problem-solving and intuition to use the bones of a deck your boss had approved for a previous project for this one so you knew it would be to her liking, and ultimately landed the client. This story would also work if you didn't land the client -- you can showcase what you learned in the process and explain how it informed your approach moving forward.

One thing to note: 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. This questions is very much about what you've learned and how you solve problems. It's okay not to be 100% literal here with the "toughest" or "biggest" challenge, but rather just a memorable, illustrative one. If you choose a current challenge, you run the risk of getting mired in whatever is driving you out of your current role, rather than focusing on how the skills you've used over the course of your career will impact your next role. 

Overall, keep this answer short and sweet. Don't give every detail of the challenge, but just enough to set the stage. Focus on what your personal role was in responding to the challenge -- not the team's role, but yours. Explain how your perspective has shifted because of this, and why you think your approach will be beneficial to the new employer.

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-- Angela Silak & Cindy Kaplan

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