How to Answer Interview Questions About Job Challenges

Being interviewed for a job
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In an interview, your potential employer's goal is to assess whether the position is a good fit for you. To determine fit, interviewers will often try to figure out which aspects of the job will be the toughest for you to master.

Interviewers will approach this problem in one of two ways. They might ask you to reflect on what you think are the most challenging aspects of the job. Or they might ask the opposite question: “Which part of this job would you find to be the least challenging?”

Before you arrive for your interview, you should think about how you will answer the "most" and "least" questions that you may hear.

How to Answer Questions About Job Challenges

As with the common interview question, "What is your greatest weakness?" the interviewer may ask an applicant what they see as the most challenging part of the job. It is important that you be honest but not rule yourself out as a candidate.

Focus on the Job Description

The best way to approach this question is to analyze the job at hand and think about which tasks will be most difficult for you based on your past experiences.

Start by breaking down the job into its various components and thinking about what you need in terms of skills and knowledge to accomplish each task. You should also think about elements of the job that will require learning or adjustments on your part.


Make sure to match your qualifications to the position's requirements.

Highlight Solvable Challenges

It is usually best to choose aspects of the job that aren't absolutely critical to your specific role. For example, if you're a journalist applying for a position as a web editor, you might mention you're working on improving your photojournalism or video skills. Don't say that proofreading or writing copy will be your biggest challenge because as a web editor these are core responsibilities of the position.


Selecting a knowledge or skill area that you lack is generally more advisable than choosing a personality trait that would be hard to change.

For example, if you're applying for a sales position, you would not want to mention that reaching out to new people makes you nervous. Instead, you might mention that you have modest skills in PowerPoint but would be glad to take workshops or complete online tutorials to upgrade your skills.

Show How You'll Surmount the Challenge

If possible, you should also discuss how you might get yourself up to speed in the least amount of time. For example, you might take a course, complete online training, or take seminars. Mention a fundamental strength you possess that would help you overcome the challenge. You could say that you've always been a quick learner.

Be Honest and Specific

When it comes to questions that require you to mention something negative, it can be tempting to give a vague response that doesn't truly reveal any weaknesses. However, dodging the question is not the way to go. For one thing, your interviewer will probably notice you're not being forthright. And for another, it can actually be helpful for your candidacy if you are aware of areas you'll need to work on and are capable of formulating a plan of action.

Examples of the Best Answers

Here are sample responses when interviewers ask what the most challenging part of the job would be:

Example Answer #1

One of my big challenges will be adjusting to the new workflow and creating a new type of report to present to clients. My plan would be to ask a lot of questions when preparing my first report. I'll also ask a colleague to review the report before sharing it with the client.

Example Answer #2

I've previously used Microsoft Word processing and presentation software exclusively and haven't used Google's online equivalents. Although I'll have to learn a whole new set of keyboard shortcuts, I'll devote time to reading blog posts that walk me through the differences between the two types of software, and I'll watch online tutorials.

Example Answer #3

I'm excited by the idea of scheduling an offsite conference, but it'll definitely be a challenge. On the plus side, although I haven't organized large corporate events before, I have planned personal events, including a 100-person family reunion, and team-wide holiday dinners for 200 people. If I get this job, one of the first things I'll do is meet with the person who organized last year's offsite event to get pointers. I'll also touch base with a former colleague of mine who orchestrated offsite conferences for her company.

Questions About the Least Challenging Aspects

Even though the employer may start by asking about the most challenging aspect of the job, they may follow up by asking about other parts of the job that would be relatively easy for you to carry out. You should be ready to share parts of the job that would be comparatively simple for you to master.

You should think of a question about the simplest aspect of a job much in the same way as you would respond to a question about your greatest strength.

Begin With the Job Description

Start by reviewing the job description and, once again, breaking the position down into its components. Then, focus special attention on the parts of the job that appear to add the most value to the organization and look for a connection to your skillset.

Focus on Most Valued Skills

It won't mean as much if you say you'll be able to easily handle the parts of the job that they don't value as highly. You can, however, make a good impression if you match your skills with what they value the most.

Be prepared to share multiple examples of similar tasks that you have successfully completed in past jobs. You should be able to describe the situation, actions which you took, skills you drew upon, and the results which you generated. Having multiple examples gives you a better chance of striking gold by matching your skills to the ones they consider key to the position and to the success of their company.

What Not to Say

You don't want to give the impression that you will be quickly bored in the job, as it will present you with no challenge at all. Respond with enthusiasm about the parts of the job that won't be challenging, perhaps focusing on skills that you enjoy using, even though you are skilled and experienced with them.

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