8 Examples of Challenges You Have Overcome At Work

Christina J Colclough

By Christina Colclough

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Expertise aside, companies also value self-aware employees who can identify their own pain points and devise excellent strategies to deal with those obstacles. That explains why hiring managers often ask you to describe a challenge you faced and how you overcame it.

Challenges overcome

Here is the chance to impress them with your outstanding interpersonal skills! Below are some strong sample answers that are sure to boost your success rate when answering this common interview question, regardless of the position you applied for.

What Challenges Have You Overcome? 8 Overcoming Obstacles Examples

1. Fixing A Coworker’s Mistake

dealing with mistake

Taking the initiative to correct a mistake made by someone else demonstrates your sense of responsibility. It also highlights your ability to work effectively within a collaborative culture and commitment towards team goals.

Example answer:

About six months ago, our team worked on a critical client project with a tight deadline. Each team member was assigned specific tasks, and I was responsible for compiling the final presentation we would deliver to the client.

As the deadline approached, I noticed a significant error in one of the data sets provided by a coworker. It was a crucial piece of information that, if left uncorrected, could have severely impacted our presentation’s accuracy and, ultimately, the project’s success.

Rather than ignoring the issue or placing blame on that coworker, I decided to take immediate action. I approached my coworker to explain the tough situation and then collaborated with him to understand how the mistake occurred. It turned out to be an honest oversight on his part, and he appreciated that I took the initiative to address the issue.

To resolve the problem, I worked closely with him to correct the data. We then updated the presentation and conducted a thorough review to catch any other potential errors. In the end, both of us met the deadline successfully.

2. Hiring Several New Employees In A Short Period

Close up interviewer
Close up interviewer

Note: For hiring manager roles

Managing the hiring process for multiple positions at the same time requires effective time management and resource allocation, from advertising positions to conducting interviews.

Thus, describing how you successfully navigated this challenge demonstrates your flexibility and great strategic thinking.

Example interview answer:

As my previous company experienced rapid growth due to increased project demands, it was crucial to quickly build a capable team that could meet client expectations. As a result, our HR team was required to hire several new employees as fast as possible. 

First, I collaborated closely with department heads to clearly define the skills and attributes needed for each role. This approach did not just help me compile more targeted job descriptions; it also ensured alignment between hiring managers and the HR team.

Next, I leveraged technology to automate routine tasks (e.g., resume screening and scheduling an initial job interview), allowing other team members to focus more on in-depth candidate assessments for a quicker turnaround time.

At the same time, I strived to foster better communication channels within the HR team and with hiring managers. Regular check-ins and status updates made sure everyone was on the same page, and any potential bottleneck was addressed promptly. I also organized training sessions for interviewers to help them improve their interviewing skills, thus resulting in a more accurate candidate evaluation. 

In the end, despite the time-sensitive nature of the hiring process, we successfully hired and onboarded a significant number of new employees. 

3. Filling in For Someone Who Had Been Fired

Problem-Solving Skills

To overcome this workplace challenge, one must quickly and effectively adapt to a new role or a set of new tasks. The hiring manager would be impressed with how you expertly navigated these unfamiliar territories despite little to no heads-up.

Example answer:

In my previous role as a Project Manager, I stumbled upon a huge challenge when a key team member was unexpectedly terminated during the most critical phase of the project. He had been responsible for client communication and project coordination; filling in for his responsibilities became the top priority.

Maintaining team morale was crucial during this transition. First, I organized a team meeting to openly acknowledge the abrupt change and address some of the project’s biggest concerns. I emphasized the importance of collaboration and assured everyone that we would navigate the challenges together.

Next, I scheduled one-on-one meetings with team members to review project documentation and seek insights into ongoing client interactions. I also worked closely with HR to recruit a replacement where possible and managed the onboarding process to speed up the integration of the new team member.

Most importantly, I still kept all our clients informed about the changes and reassured them of our commitment to delivering high-quality results. And we kept our word: the project concluded successfully. Even better, this experience led to significant process improvements that positively impacted the team’s long-term efficiency. 

4. Learning A New Skillset To Stay Relevant

An excellent, dynamic employee should be able to catch up with the evolving industry trends. Staying open to changes is not enough; you must proactively seek ways to counter them.

Example answer:

Once, my previous company decided to adopt a new customer relationship management (CRM) software to assist our marketing strategies. Right then, I realized I needed to learn to use this tool quickly and efficiently to contribute to the team.

This challenge wasn’t as simple as it sounded. For one, the CRM software significantly differed from our previous system, requiring major shifts in my data analysis and customer segmentation. Not to mention, there was a tight timeline; our team must be trained and fully operational on the new platform as soon as possible to avoid disruptions in ongoing campaigns.

Self-learning was the key; I leveraged all available online resources and training modules provided by the software vendor, even participating in webinars. At the same time, I sought advice from the IT department and attended on-site training sessions to understand the technical aspects and potential integrations with other marketing tools.

And since a collective understanding among the entire team is crucial, knowledge sharing was my next step. I prepared comprehensive guidelines and conducted hands-on workshops with the help of some other trusted colleagues. During these sessions, I always encouraged open discussions among all members to address existing challenges in adapting to the new platform.

Despite the initial learning curve (and, of course, some resistance to change), my efforts paid off, and our team successfully transitioned to the new CRM system within two weeks.

5. Dealing With Missing Cash After Your Shift

Dealing With Missing Cash

Note: for cash-handling roles, such as cashiers

This experience highlights your commitment as a trustworthy, reliable employee who takes ownership of their own responsibilities. Problem-solving skills must also be involved; show them how you analyzed the situation to identify root causes and come up with effective solutions.

Example answer:

After one of my shifts, I noticed the till was short by a noticeable amount.

First, I reviewed all the transactions from my shift and cross-referenced them with receipts and the electronic point-of-sale system. Soon, I discovered one specific transaction that seemed to be the source of the discrepancy.

I then consulted with my supervisor to explain the situation thoroughly, providing evidence of the transaction in question. We decided to review security camera footage to gain further insights. 

It turned out that there was a genuine error during the transaction, where a customer was undercharged due to a technical glitch in the system. As a result, they had unintentionally received more change than they were supposed to! 

Now that the root cause was identified, I approached the customer to explain the error and request the return of the overpaid amount. Fortunately, the customer willingly returned the excess without much protest. 

This experience taught me the importance of attention to detail. From then on, I always scanned through the point-of-sale system before every exchange to address potential technical glitches that might contribute to transaction errors. 

6. A Difficult Ethical Decision

This personal challenge underscores your dedication to upholding moral principles – a crucial quality in any professional setting. Here is also where your decision-making skills shined through, as you had to weigh various factors to make an informed, conscientious choice. 

Example answer: 

During the quarterly financial review, I uncovered an error in the calculations that, if left uncorrected, could have led to the overstatement of our company’s profits. 

On the one hand, correcting the error meant acknowledging a shortfall in our profits, which could negatively affect the company’s stock value and investor confidence. On the other hand, failing to rectify the mistake would clearly compromise the integrity of our financial reporting. 

So I made my decision. I immediately informed my supervisor about the error and provided a detailed analysis of how it occurred. 

We then worked with the finance team to conduct a more thorough review of our financial reports, identifying any other errors that might have gone unnoticed. I also briefed the company’s audit committee on the situation to maintain the trust of both internal and external stakeholders.

The outcome was, unsurprisingly, a revised set of financial reports that accurately reflected our company’s financial position. While the correction did lead to a temporary dip in stock value, the subsequent investor relations strategy helped rebuild trust regardless; it was a win-win situation at the end of the day.

7. Resolving Conflicts Between Coworkers

Your strong interpersonal skills will receive their spotlights here. Specifically, the answer demonstrates how you understood different perspectives and navigated your relationships with both parties to work towards collaborative solutions.

Example answer:

As a Project Coordinator, I used to help resolve a persistent conflict between two team members; let’s call them Mark and Lisa. 

Mark, primarily responsible for coding and development, believed that Lisa, in her role as the project manager, had communicated unrealistic deadlines for certain features. On the other hand, Lisa thought she had clearly outlined the project timeline and expected deliverables during the kickoff meeting.

I facilitated a focused meeting between Mark and Lisa to discuss their expectations. During this private meeting, it became evident that there had been a breakdown in communication regarding the project timeline, and each team member had a different understanding of the critical milestones.

To address that misunderstanding, I provided a more structured project communication plan, which included regular project update meetings where team members could openly discuss progress, potential roadblocks, and adjustments to deadlines if needed. Furthermore, I also proposed a new project management tool to centralize project timelines and task assignments through visual references for the entire team.

My conflict-resolution efforts eventually mended the relationship between Mark and Lisa. Even better, it fostered the project’s communication and collaboration as a whole. 

8. Dealing With A Very Hostile Client

This difficult situation requires a high level of emotional intelligence. Overcoming this challenge successfully means you have managed emotions well (both your own and the client’s) and provided excellent service while still maintaining professionalism.

Example answer:

One of our clients, frustrated with delays in key project milestones and what he saw as “communication lapses,” expressed his dissatisfaction in an aggressive and very confrontational manner.

These delays stemmed from unforeseen technical challenges that arose during the coding phase of the team project. And given the compatibility issues with existing systems and unexpected bugs, the issue eventually led to a reevaluation of our initial project timeline. The client claimed that he “did not sign up for such unforeseen setbacks” and demanded immediate solutions.

I maintained a calm, composed demeanor regardless of their accusations. Together with other teammates, I explained the specific technical challenges we encountered and how we addressed them and outlined the revised project timeline. I also detailed the roadmap for the remaining project phases and promised to provide more frequent updates from then on.

Despite his confrontational attitude, this angry customer eventually approved our proposed solution. As he became more engaged and less accusatory during the rest of our brainstorming periods, the project ultimately reached its successful conclusion.

See more interview tips:

For Interview Question:


When reciting what obstacles you have overcome, do not dwell too much on the nature of those work-related challenges. Instead, I recommend using them as a canvas to highlight your relevant qualities, such as problem-solving, communication skills, or excellent teamwork spirit. 

Write to me if anything else troubles you along the way!

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Christina J Colclough

Christina J. Colclough

Dr Christina J. Colclough is an expert on The Future World of Work and the politics of digital technology advocating globally for the importance of the workers’ voice. She has extensive regional and global labour movement experience, is a sought-after keynote speaker, coach, and strategist advising progressive governments and worker organisations.

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