Preparing for a job interview is a daunting task for most candidates. One of the concerns applicants have is that they’ll be asked a challenging question that they don’t know how to answer. These questions can range from generic ones like “tell me about yourself” to position-based questions that you may not have the experience to answer.

When thinking about how to answer difficult job interview questions, you must keep a range of things in mind. From understanding why the question is being asked to knowing how to turn a question you can’t answer around without making you look underqualified.

If you’re concerned about an upcoming interview, read on to learn some important tips for answering the most challenging interview questions.

Why Do Hiring Boards Ask Difficult Job Interview Questions?

The first step in knowing how to answer difficult job interview questions is understanding why they are being asked. Interviewers will ask challenging questions for a range of reasons, including:

To see how you react under pressure and in unexpected situations
To get a look at your thought process
To determine how comfortable you are with certain tasks and your skill level. For example, they may ask about something that they don’t expect someone applying for the position to necessarily know. If you do know how to talk about the topic or have some idea, that’s a plus.

Like with all interview questions, more challenging questions are being asked to get the information the hiring board needs from you about your experience, skills, knowledge, and personality.

A woman in a withe shirt answering interview questions — One reason for being asked difficult interview questions is to see how you act in unexpected situations.

How to Handle Difficult Questions in an Interview

If you prepare in advance for your interview and keep in mind the below tips, answering difficult job interview questions will be less of a struggle.

Do Research and Prep Beforehand

Do some research beforehand and think about what questions you could be asked. If you struggle to think of an answer to any of these questions on the spot, take some time to prepare a brief response. It can also help to think about questions that you have struggled with in the past at interviews and develop answers for those questions.

Practice Answering Questions

To be successful in answering difficult job interview questions, practicing before the interview is crucial. A suggested way to do this is by finding mock interview questions, both general and relating to the position you’re interviewing for, if possible.

If you know anyone that interviews people regularly, you can also ask them to hold a mock interview with you. Request that they ask as many challenging job interview questions as they can.

Be Yourself and Answer Authentically

Always be yourself during the interview and answer difficult questions authentically. Never lie when answering a question because you don't have real life experience to back up an answer.

A person typing on a laptop with notes next to them — Before the interview, do research on challenging questions that may be asked.

Think About Why They Are Asking the Question

All interview questions are asked for a reason. As mentioned above, questions may be asked to learn more about your experience and knowledge, but could also be asked to get an idea of how you think and solve problems.

In the interview, think about why questions you cannot answer are being asked, and then devise a response based on that. For example, if the question is being asked to see if you have experience in a certain area, say you don’t but that you’re eager to learn about it. You could also highlight work experience that you do have that is similar.

Say You Don’t Have an Answer, But Put a Spin on the Question

In the worst case, be upfront and say you don’t know the answer. If doing this, stay calm and professional. As briefly discussed above, try to pivot the question instead of simply saying that you don’t know.

You could talk about work experience you do have or ask a question of your own that could give you more information on the type of response the hiring team is after. You can also say that you don’t have experience relating to the question, so can’t answer, but would like to learn about the topic, and that is one of the reasons you’re interested in the position.

If you get asked a question at multiple interviews that you can’t back up with experience, consider ways you can increase your work experience before applying to similar positions.

Have an Extra Copy of Your Resume for Yourself

You should always take copies of your resume to the interview for the hiring board. But also have an extra copy of your resume for yourself. Having your resume in front of you offers a quick and concise reminder of your experience, skills, and qualities.

Need some more interview technique advice? Check out these top interview tips for candidates!

7 Most Difficult Job Interview Questions and How to Answer Them

Now that you have some general tactics for handling challenging questions, be sure to read over these seven difficult job interview questions and answers.

1. Tell Me About Yourself

This question is almost guaranteed to get asked in an interview. The challenge here is that it is a vague question. It doesn’t highlight exactly what the interviewer wants to know about you.

Do they want to know more about you as a person and your education? Or do they want an overview of your career? Or an overview of just your last position? A good way to determine this is to ask! You could ask if they would like to know about your academic background, employment background, or both, for example.

If you don’t feel comfortable asking that, give a quick overview of your education and career progression before focusing on recent employment history, especially tasks and positions relating to the position you're interviewing for. Also, highlight why you are passionate about your industry and role and try to expand on things listed on your resume, don’t just repeat it.

Try to keep this answer short and to the point; your response should last about a minute.

2. Why Did You Leave Your Last Job? / Why Are You Looking to Leave Your Current Position?

Answering this question doesn’t need to be challenging and should be relatively easy to answer if you’re truly interested in the position and company. However, you must be careful with the reasons you give for wanting to leave your current position.

Even if you are leaving for negative reasons such as poor management or a toxic work environment, never mention that. Explain how you have acquired everything you can from your current position and are looking to find a role where you can:

Learn more
Take on more responsibility
Feel more challenged
Work within a different organizational structure
Work on tasks and projects not available in my current position

Then explain why you feel that this position and company offers you that. Also, never mention superficial factors, such as looking for a new position that offers a higher salary.

If you like your current role and organization but are leaving for reasons such as moving to a new city, mention that. Say that this company and position appeals to you as you notice similarities with your previous role that you loved and thrived in.

Variations of this Question

“Why are you currently out of work?”

In this case, simply be truthful about why you’ve been out of work (as long as the reasons are professional.) Then, explain why you’re looking to get back into the workforce, specifically at this company in this position.

“What did you dislike about your last/current position?”

Any question relating to negatives (dislikes, weaknesses, etc.) can be challenging to answer and require a calculated response. Think about what you didn’t like but phrase your response in a way that shows you want to grow. Never be overly critical about a previous employer, manager, or co-workers either.

For example, if you dislike that your manager micro-managers you, mention that you don’t get the independence you would like at your current company. Then add that you’re looking to take on more freedom and responsibility in a new role and work within a flatter hierarchy.

When explaining why you are looking for a new role, don’t say overly negative things about your current company.

3. Why Do You Want This Job?

Again, if you’re passionate about the position and organization you’re applying to, this question shouldn’t be too much of a challenge. When answering this question, make sure you show your enthusiasm for the position and the company and its mission. You also want to highlight why you’re a good fit and how the role plays into your ideal career path. We will now discuss these points more.

Show Enthusiasm for the Organization

When discussing why you want the job, mention what appeals to you about the position and the company. For example, your values may align with the company’s goals and mission. Or, you might have been interested in working for the organization for a while since you first encountered it.

Another reason you can give is that you value the company’s culture and see yourself as an ideal cultural fit. Whatever reasons you provide, be sure to show lots of enthusiasm for the organization as a whole and the specific job position.

Mention your Desired Career Path

You can tell the hiring board why you want the job by explaining how the role fits into your career growth path. Mention factors that make this role a good fit for your career goals. For example, if the company often promotes from within and/or offers learning opportunities and mentorship programs that can help you grow.

The hiring board will appreciate the fact that you have a career plan and a desire to grow and that you see yourself with the company long-term. When discussing this, mention what you bring to the company in return as well so that your answer isn’t one-sided.

Connect Your Skills, Knowledge, and Experience with the Role

When answering this question, you can also discuss how your skills, knowledge, and experience align with the role and that you are interested as you think you’re a perfect fit. However, you must focus on the company and the role and what they will provide you the most as opposed to only stating what you bring to the company, which will probably have been discussed already.

4. What Are Your Greatest Weaknesses?

As discussed, questions relating to negatives, such as your weaknesses, can be challenging to answer. “What are your greatest weaknesses?” is a very common interview question, yet many still struggle with it.

You always want to ensure that the weaknesses you choose don’t correlate to the main responsibilities of the role. Also, mention how you are working to fix this weakness.

For example, if you don’t enjoy creating reports, but you only have to do this once a week in the role, that could be an appropriate weakness to use. Say that you sometimes put off that task until the last minute in place of working on core projects. But highlight that you work hard to set a specific time to tackle your reports and schedule enjoyable tasks directly related to your role before and after creating reports to avoid putting them off.

You also don’t want to use cliche responses that aren’t “real” weaknesses. For example, that you work too hard or are too much of a perfectionist.

5. Explain a Time You Dealt with Failure / How Do You Learn from Your Mistakes?

This question is quite likely to come up, so think about some mistakes you’ve made or times you failed before you go to the interview. The key to answering this question successfully is explaining how you dealt with the issue and learned from it. You should also take responsibility for the mistake from the start.

Try to use a professional example, but if you’re newer to the workforce and don't have any examples, think of a time you made a mistake or failed at school or in a volunteer position. Once you state the problem that occurred, explain how you were proactive in dealing with it and ensuring the error doesn’t occur again/how you learned from the situation to make you a better employee today.

A woman talking to two other people at a job interview — When discussing weaknesses, don’t mention things that correlate to the role’s main responsibilities.

6. Where Do You See Yourself in Five Years?

Hiring boards ask this question as they want to assess your loyalty to a company; do you see yourself growing within the company over the next five years? Or do you have other plans?

They also want to assess your motivation and desire to grow and see if your career goals match what they can offer you. If they feel the company can’t offer you what they want, they may not offer you the position as you’ll probably leave the company quickly. While this sounds negative, in the long run, avoiding a role that doesn’t match your career goals is a good thing!

When answering this question, mention a clear set of career goals and tie them into the job and organization. For example, list four specific goals and how you believe the company will help you achieve each. Stick with goals that are attainable in five years for someone of your current experience.

7. What is Your Desired Salary?

Discussing salary can be uncomfortable for both the candidate and the hiring board. However, many interviewers will ask this question to get a sense of if their top applicants fit into the company budget.

The issue with this question is that you don’t want to suggest a salary lower than your worth to “please” the hiring board as you may end up missing out on the top value they would pay. Many candidates are also afraid of giving a value that is too high and being rejected solely on that response.

There are a few ways to deal with this question, as discussed below.

State the Value You Feel You Deserve

If using this tactic, ensure you’ve done research beforehand. Look up average salaries in your area for the responsibilities of the role and your experience level. Then, generate a salary value based on your research that you believe you are worth in the current market.

State this value when asked but say that you are open to discussion if that doesn’t fit into their budget (as long as you would be willing to earn less than the stated value.)

Say You Would Rather Discuss Salary When You Have an Offer

You can also say that you would rather discuss a salary once an offer is on the table. This is a fair response as many employees will adjust salary expectations based on benefits and other perks offered. It’s still a good idea to have a desired salary in mind, backed up by research, in case the interviewer pushes you on this question.

Ask the Hiring Board What Budget They’re Working With

As with candidates, hiring teams often avoid saying the salary range they have in mind for fear of paying more than the candidate desires. However, responding to this question with a question can be a successful technique to use.

If you’re in the final stages of the hiring process, your interviewers may be more likely to say what they think you’re worth or disclose the salary range they have to play with. You’ll then have a better idea of if your desired salary is achievable, or even if you could request more than that.

Want to prepare for when you get the job? Read our advice on negotiating a job offer successfully.

In Conclusion

One of the most common questions asked when preparing for an interview is: “How do you deal with difficult interview questions?” The fear of a challenging question being asked adds greatly to the tension felt before an interview.

However, responding to difficult interview questions doesn’t need to be daunting. By keeping the discussed tips in mind, you’ll be able to craft thoughtful responses that impress the interviewers, even if you don’t have a direct answer to the initial question.

If you need more help preparing for interviews, get in touch with our experienced team at Lynne Palmer. Along with connecting you with incredible job opportunities in the publishing and medical communications sectors, we aid with job applications and interview prep to make the chance of you securing your dream job exponentially higher!

How to Answer Difficult Job Interview Questions