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What is the toughest problem you've had to face? And how did you overcome it?

1 of 17 Direct Interview Questions and Answers Written by Rachelle Enns

Written on June 29th, 2018 | Rachelle is a job search expert, career coach, and headhunter
who helps everyone from students to fortune executives find success in their career.
How to Answer

The interviewer is looking for an example from your work history. Avoid giving a personal example, unless you can very clearly tie the story back into your career. You do not want to be overly long-winded here. State the problem, how you approached it, and what the result was. If you received any accolades for your ability to problem-solve, you could discuss that as well.

Professional Answer Examples
Answer example

"The toughest work problem that I have faced recently was when our business went all systems down in the middle of tax season. We had our IT department on the issue immediately, but the situation took a couple of days to fix completely. At tax time, two days behind feels like years. I overcame the issue by staying an extra three hours late for five days. This commitment ensured I was ahead of the game again. It was a stressful time indeed, but nothing a little extra effort could not repair."

Answer example

"The most challenging problem I have faced was when I accidentally deleted a significant amount of important files from my computer, due to mislabeling them. I told my boss immediately and was incredibly embarrassed about the situation. This level of mistake had never happened to me before! I owned up to the situation immediately which made it much easier for our tech team to recover the files. Rest assured, I know what I did wrong and take every possible step to ensure it never happens again."

Answer example

"The toughest issue I have had at work was with my previous company. Our regional director and my territory manager quit in the same week. The CEO asked me to split their workload with two other territory reps. Unprepared nor trained correctly, but I did the best that I could with the resources that I had. With my clients, I explained the situation professionally and asked them upfront for their patience as I learned my new role and responsibilities. Eventually, the positions became filled again and I was off the hook. It was a learning experience, in a pressure cooker environment!"

Answer example

"Earlier in my career, I worked for a marketing director who I did not get along with at all. I am easy to get along with because I practice a mentality of 'kindness first.' This particular director took that as a weakness and tried to railroad me verbally on a daily basis. I had never experienced this type of treatment before, and have not since. I did give my notice to that position before my professional reputation or integrity took a hit. I am a loyal person, so the decision to leave was one of the most challenging of my career."

Answer example

"The toughest career challenge that I faced was when my previous organization went into receivership. I had to help with blowout sales and questions surrounding the retailers very public bankruptcy. Customers were calling in a panic regarding their gift cards, and employees were quitting every day. I had other organizations trying to poach me to work for them, but I decided to stick with my job until the very end. I am glad that I did because loyalty is important to me and I wanted to maintain a good reference."

Answer example

"The biggest challenge I faced in my career was breaking into the SaaS business. Software sales are incredibly challenging and competitive by nature. To prepare for an opportunity, and to make myself a competitive candidate, I took multiple specific software sales courses for an entire year. The knowledge I gained was immense, and my dedication paid off."

Answer example

"The toughest challenge that I face, and I meet it on a regular basis, is lobbying for proper assistance and help in the classroom for students with learning disabilities. Public school budgets often do not allow for the great resources that are out there. To overcome this, I call to my community for help, lead fundraisers, and contact local non-profit agencies to ask how they can assist. The opportunities provided to my students through my added efforts have been vast."

Elementary Teacher
Answer example

"I had a violent student who would lash out at students and staff. I had to be very patient with him and I had to remain very calm when dealing with him because I knew that, if he saw my stress or any sign of aggression, he would lash out even more. I overcame the problem by showing him compassion."

Physical Therapist
Answer example

"The most difficult problem I faced recently was working with my schedule to get two walk-in appointments in between scheduled patients. I made a point to explain to the walk-ins that I would do my best to get them in but they may have to wait a bit. The fact that I was up front with the possibility that they could wait made them understand why they had to wait a bit longer than normal. After communicating with my team, another therapist was able to help out with one of my regularly scheduled appointments and we made the situation work."

Answer example

"One of my co-workers wasn't carrying their weight, which meant everyone else had more work to do. I chatted with her one day at lunch, and she shared some personal issues that had been interfering and we agreed she needed some help with her projects. We all met with our boss and we determined a temporary solution to help her while she resolved her issues outside of work."

Answer example

"One roadblock I recently encountered was when I was tasked to replace defective parts on one of the lathes only to find out that the particular part was on backorder with our supplier. I was able to track one down online and had our supplier purchase it on our behalf and then ship it. It was a longer work-around than I would have liked but it got the job done."

Ticket Agent
Answer example

"A big challenge I have had to overcome was when working as a/an (X position title) for (X company). I was responsible for (X duties) and one day I (X example of a big challenge). I nevertheless remained calm, collected and professional and did not let this situation affect my performance."

Court Clerk
Answer example

"My biggest challenge as a court clerk was learning all of the legal jargon. It's endless! I spent many hours studying, working weekends, and taking additional coursework so that I could come to work confidently in my knowledge."

Proofreaders and Copy Markers
Answer example

"Truthfully, no professional obstacles or major challenges come to mind. I believe my high degree of meticulousness, as well as my other skills and educational/professional qualifications ensured negative or significantly challenging situations would rarely occur."

Written by:

Rachelle Enns
Rachelle Enns is a job search expert, executive headhunter, career catalyst, and interview coach. Utilized by top talent from Fortune companies like Microsoft, General Electric, and Nestle, she helps professionals position themselves in today's competitive digital marketplace. Rachelle founded Renovate My Resume and Executive Resume Solutions, two companies focused on helping job seekers get their edge back. She helps everyone from new graduates looking for their first placement, to CEO's who want more out of their career. Rachelle coaches students to executives on how to master the toughest interview questions and how to handle the most bizarre interview situations; all with confidence and poise. Rachelle trains other career coaches, recruiters, and resume writers, globally. A big part of her job is also spent coaching HR professionals on how to bring the human touch back into their interview and hiring process.
Ryan Brown
Ryan Brown, is the creator of MockQuestions. He has over ten years experience creating interview questions. His website has helped over 10 million job seekers in their interview preparation.
Published: 06/29/2018
*Specific career answer examples vary on published date

View user-submitted Answers

What is the toughest problem you've had to face? And how did you overcome it?
I had to face myself and improve who I was as a person. It is easy to overcome challenges and obstacles at work because there is always help available but facing your own demons is an entirely different situation all together. I am not the person I once was. I am more mature. I am more patient, I am and a better person. Once I fixed myself, with help of a support network, I am confident I am able to face any problem and overcome it.
Well the toughest decisions that I had to make was leaving my job that I was employed at for seven months I left behind my colleagues and friends but I learned how to cope with this lost by keeping in touch with my co- workers.
The toughest problem I had to face was when the time the computer crashed right at month end. Instead of the inital response of panicking I contacted my IT department to see if I could retrieve the material somehow. After about 35 minutes the result was successful once the power came back on and the system had an autosave..
Friends will not co-operate with the work, its highly irritating. Just be patience and had tolerance. Slowly cope up with them and complete the work.
Losing the data in a system crash and had a deadline to meet. Had to work around the clock to restore and get back the data and finish the project on time.
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