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Tell me about the most challenging problem you have encountered in your professional career.

1 of 25 Problem Solving Interview Questions and Answers Written by Rachelle Enns

Updated 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

Everyone has had their share of challenges in their career. The interviewer knows that you are not perfect; however, they need to know that you can professionally overcome work-related roadblocks. Maybe you had a significant project that almost went sideways. Perhaps you had a conflict in the workplace that you could have handled more professionally. Explain your approach to resolving the issue and be sure to highlight the steps you took to reach that resolution.

Professional Answer Examples
General
Answer example

"The most challenging problem I have encountered in my professional career was with my most recent employer. I had an incredibly important project that made up the majority of my annual budget. The client was challenging to work with as he was rarely available for comment, due to extensive international travel. I needed this deal to work out so, for the 6-month span of the project, I made my work hours reflect his time zone. This shift allowed us to communicate via Skype on a daily basis which meant a fair share of late night and early morning calls for me! It was a sacrifice, and I would do it again. I understand that sacrifices need to happen to gain successful outcomes."

Admin
Answer example

"The most challenging problem that I encountered in my career was when my former company experienced a major merger. It was a lot to adjust to but, after some time, I was able to get a good pace again."

Manager
Answer example

"The most significant challenge I have faced as a manager would be the labor dispute and lockout that our company went through in 2016. Many of our permanent employees are union based. We could not come to a new collective agreement, and so I ended up having to utilize a lot of temporary staffing options during that time. It was a lot of re-training, and strain on the company culture overall."

Marketing
Answer example

"The biggest challenge that I face as a marketer, and it's an ongoing challenge, is to manage my expectations on projects. I lean on the side of perfectionism and often put more pressure on myself than even a client would. The positive side of this; however, is that I always deliver an immaculate product."

Retail
Answer example

"I'd say the most challenging problem I have encountered was when my manager suddenly resigned. I was then in charge of the department. Now, I was mostly ready for the responsibility, as the assistant manager in the department. However, I had never completed inventory reconciliation, and on the first day, this was my first task. I was asked to give projections so that our buyer could stock us for next season. I had no idea what to do, so I researched until I came up with the answer. Also, other managers in other departments helped to guide me. Ultimately the work paid off because our next season projections were perfect. Since then, I've learned more effective ways to do our inventory management and projections, but I don't think I've ever learned anything as quickly as I did that week."

Sales
Answer example

"The most challenging problem I've encountered is the misstep of taking my current role. The initial pitch to me on company growth and my duties is not my reality. This factor has been a challenge to my career growth. I know that even if it was a misstep, there are lessons to be learned, and I approach each day with interest and a positive attitude to try to learn those lessons and grow professionally."

Teacher
Answer example

"The most significant challenge I've faced is nearly having my department eliminated due to budgetary cuts. I was lucky to have an active parent community rally behind me and the department which saved the program, in the end. The other challenge that comes to mind was getting back into the swing of teaching after taking a few years off to be home with my children. There was a learning curve on getting up to speed with curriculum and the lesson planning, but my love for teaching made it all that much easier!"

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.
First written on: 06/21/2016
Last modified on: 06/29/2018

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