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Tell me about the most challenging aspect of your previous job. How did you overcome it?

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

Sometimes the most significant workplace challenge is a difficult task that puts you outside of your comfort zone. It could be something that requires skills you haven't mastered yet or qualities where you are not the strongest. Explain to the interviewer why it was difficult but be sure to spend more time highlighting the actions you took to overcome the challenge.

Professional Answer Examples
General
Answer example

"The most challenging aspect of my last job was troubleshooting some of the older technology. We needed some serious upgrades, but they weren't in the budget. Learning how to work around this problem was quite a challenge, but I learned how by referring to old manuals and online forums. I ended up to become one of the stronger users of this program, in our entire office! I quickly became the go-to person when anyone had questions about the technology."

Admin
Answer example

"In my current role, we have global offices that span four time zones. It is an incredible challenge to be continually calculating the difference in my mind when I call or email on updates for projects, for instance. I now have each locations time added to my desktop, my smartphone, and four individual clocks on my wall. These small and inexpensive changes made all the difference."

Manager
Answer example

"The most challenging aspect of my previous job was the constant need to pivot when it came to trends in the industry. We would gain footing, and then the next greatest product would arrive. It made it difficult to feel loyalty to any of it. I started to express loyalty to the company's ability to discern great products instead of narrowing in on the products themselves. This shift in thought helped with mine and my teams' performance when it came to sales."

Marketing
Answer example

"My previous role was with a small agency where budgets were always a concern by the clients. Although I liked the clients, they were usually independent businesses with less than ten employees. They had a hard time thinking big-picture. I overcame this by coming up with a questionnaire that would address their greatest pain points and needs for their business. I would then focus on their small goals versus what I felt their company could be. Some business owners are more comfortable being comfortable, versus ruling the world, and that's okay! I just needed to wrap my marketing brain around that."

Retail
Answer example

"The most challenging part of my prior role was navigating the landscape as the newest manager on the team. I needed to work on gaining the trust and respect despite my being green. I worked hard to build individual relationships with each associate and forge a bond with them. I also shared information about myself, including my experience in the industry, and who I am as a person. I know that this made me more human, approachable, and also solidified my credentials, so I know how to get the team on my side."

Sales
Answer example

"The most challenging part of my previous job was relying on another team to be efficient. I am all for teamwork, but for me to be paid, this team needed to deliver timely and quality work. Meanwhile, their goals and metrics remained disconnected to any sales outcomes. This situation made it tough to motivate them. In the short term, I sat down with them and explained why it was vital for myself them, and the company that we work together on the same timeline. I incentivized them with coffee or store gift cards. Bigger picture, I sat down with the management of both teams and shared the issues we were having, suggesting a solution that would tie their KPIs and financial incentives to our outcomes, to make them invested. In the end, the short- and long-term approaches proved useful."

Teacher
Answer example

"I think the most challenging aspect of my current job is the fact that I share a classroom with another educator. Without having my space, other obstacles come up such as teachers trying to influence how I run my class, or them holding small conversations with their aides during my teaching time. I make sure to address this up front with the classroom teachers- that while it is also their room, please treat it as though it were mine during the 40 minutes that I am teaching. If there is ever an issue, I am sure to address it quickly and directly, so we can move past it."

Wildlife Biologist
Answer example

"A difficult project 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 further information regarding this difficult project). I nevertheless remained calm, collected and professional and did not let the difficulty affect my performance."

Wildland Firefighter
Answer example

"When I worked as a logger we spent days chopping down trees and it was physically exhausting. Even though it could be monotonous work at times, I learned about perseverance and teamwork. My team and I got along great and even had fun while we worked!"

Power Plant Operator
Answer example

"I have overcome many difficult challenges in the workplace and often have challenging projects on the go. The most recent project that I can recall working on was my participation in a plant-wide audit. The challenges faced included co-operation from all staff, accuracy of data and the analysis of our findings. I took the project on as a learning opportunity and kept an open mind. This allowed me to successfully complete the project without becoming overwhelmed."

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: 08/16/2016
Last modified on: 06/29/2018

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