Best Interview Questions to Ask Job Candidates – Overcoming Obstacles

This is part nine of a 12-part series.

Creating a successful and productive team starts with finding great employees who fit your organizational culture. And while you may receive hundreds of job applications and interested parties, narrowing down the talent pool to hire the right candidate for the job goes beyond what hiring managers can surmise by reading cover letters and applicants’ resumes, especially when studies show 85% of applicants lie on their resumes. This is where the art of the interview comes into play.

According to a study, although a typical interview averages 40 minutes, 33% of hiring managers decide whether they want to hire a job candidate within the first 90 seconds of an interview. To ensure you’re completely thorough and make the right decision, it’s important to ask the right questions to fully understand and evaluate a candidate. During this 12-part series, we will explore the best interview questions to ask job candidates and give a few “pro tips” along the way.

Part Nine – Uncovering an Interviewee’s Ability to Overcome Obstacles

Question: Tell me about a time you had to handle a difficult situation at work?

Follow ups: What did you do to fix the situation? What did you learn from the challenge to help you work through similar situations in the future?

In one of our first installments of the “Best Interview Questions to Ask Job Candidates” series, we tackled an important issue concerning how candidates deal with conflict in the workplace. While asking a candidate to share an example of dealing with conflict helped uncover the interviewee’s confrontation style, as well as the ability to mitigate negative outcomes, this question similarly helps the hiring manager dive into stress management and how a potential employee works through difficult and challenging seasons.

By asking candidates how they have handled difficult situations, there is an assumption that there will always be obstacles in the workforce. However, it’s important to see what workers do during either trying times, a missed deadline, a failed project, etc. And when working with others, issues may arise that affect the project officer, regardless of who is at fault. An ideal candidate takes ownership and takes proactive steps to fix or mitigate a crisis, allowing the team to succeed as a whole.

Negative situations aren’t necessarily a referendum on a team. It’s what happens when obstacles arise that showcase the mettle and resolute nature of the team to work through an issue. Moreover, it’s important to understand that difficult situations are opportunities for employees to better plan for similar future situations, as well as know best practices and solutions for when the next issue arises.

Ask follow-up questions to dig deeper into how the problem affected others around them and how they helped the team succeed on the other side of the problem.


You may find that any time you ask a candidate to bring up a negative situation they have dealt with it can be difficult to get deeper answers. Not everyone enjoys talking about obstacles or conflict, especially if they see it as complaining. Moreover, some candidates may have been coached to never showcase struggles or weaknesses during interviews. If your candidate is like this, it’s not necessarily a major issue; it can be more of a personality and cultural approach to difficult conversations. Try to give the question a positive spin to extract a meaningful answer.

What is your favorite question to ask a job candidate? How do you decide who the right candidate is? Let us know in the comments section below!

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