What Was the Toughest Challenge You’ve Ever Faced?

Nilda Melissa Diaz By Nilda Melissa Diaz, Career Advice Contributor Last Updated: May 25, 2023

The question “What was the toughest challenge you’ve ever faced?” is one of many company’s favorite interview questions. Its designed to gather insight into your resilience- dedication and overall ability to lean into a less-than-ideal situation. This question can be a gift and a curse: It lends itself to a positive answer- providing the perfect opportunity for job applicants to showcase their best and brightest skills. But it is very open ended and can be hard to answer on a dime. We all face countless challenges in a lifetime; which is the most relevant to the job interview?

Tired women working on the computer late at night

It’s easy to get lost in thought and lose precious time as you struggle to craft the best answer. That can waste valuable interview time and make the wrong impression on your potential future employer. Instead- formulate a strategy and you won’t get tongue-tied trying to answer this staple of job interview questions.

How to Answer the “What Was the Toughest Challenge You’ve Ever Faced?” Interview Question

Think of a valuable workplace skill you want to emphasize

Perhaps you are an excellent communicator. Maybe your organizing skills are second to none. Or perhaps it’s data management that sets you apart. Whatever it is- think of what unique ability you bring to the table; then think of how you used that to overcome a challenge. Maybe you have a preternatural ability for detecting problems in processes or products. Think back to a time when your nose for product problems helped you spot a small issue before it became a big- costly one. Then walk your interviewer through the steps of discovery- planning a solution and implementation- as well as the end results. Interviewers are bound to be impressed by your ability to zoom in on a specific problem and a specific solution.

Think beyond the workplace

It’s natural that some of our biggest challenges are faced not in a work setting but in our personal lives. There’s nothing wrong with mining those experiences to craft the perfect answer to this interview question. It may seem risky to get personal in an interview. But believe it or not- hiring managers asking this question are often interested in learning more about what makes you tick as a person- not just an employee. They may be looking for insight into your personal resilience and your willingness to try again- not to mention how you look at challenges. Are you a glass-half-empty or half-full person? Do you see the world through rose-colored glasses- or is there a perpetual cloud of negativity darkening your thoughts? All of these can be detected by listening to what you consider a challenge and how you respond.

Don’t forget the details

When you’re nervous it’s easy for the ideas to seemingly disappear from your head. That’s when we turn to more general answers such as describing a workplace conflict as something “we worked out” or a personal obstacle as “something I eventually overcame.” Those answers are too vague and general to give the interviewer what they’re really after: a glimpse into your personality. When answering “What was the toughest challenge you’ve ever faced?” be prepared with all of the pertinent details of your challenge and redemption- with emphasis on qualities that are applicable to the workplace.

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