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How to ask and answer tough interview questions


It’s essential to know how to ask and answer tough interview questions.


You only have an average of 40 minutes[1] and a limited number of questions to get to know a candidate. During an interview, you’re usually seeing them on their best behavior.

It can be hard to get a glimpse of how they operate under stress, communicate with team members, or get back up after a failure.

What about the classic, tried-and-true questions?

“Could you describe yourself in one word?”


Asking clichéd questions will only get you clichéd answers. The chances are that interviewees have already prepared for them.

Deep, probing interview questions dig into the knowledge you need from your applicants and show you their values, competencies, and experience.

We’ll talk about how to answer tough interview questions, how to ask them, the answers you should look for, and why these difficult questions are essential to your hiring process.

Why tough interview questions and answers are important

A typical job interview lasts 90 minutes at the most – 40 minutes less than the average film, which sits at 130 minutes.

That’s how long – or short – you have to dig into a candidate’s skills, experience, and values.

It can be tricky to uncover all that information with standard questions like “Why do you want to work here?

Knowing how to conduct an interview properly can be challenging.

But deep, difficult questions help you get the most out of an interview. They give you valuable insights into a candidate’s experience, personality, and thought processes.

For example, you can use an unexpected, abstract question to see how an individual answers rather than what they answer.

A question like “If you were an animal, which animal would you be?” isn’t looking for a specific answer. This type of question judges if the candidate can answer quickly and back their logic with an explanation.  

One-third of recruiters think they can judge if a candidate is perfect within the first 90 seconds – but let’s take advantage of the full 90 minutes, shall we?

Difficult questions will help you discover more information about the candidate and show you how they react to sudden, unexpected circumstances.

Tough interview questions will put the candidate on the spot in a positive way, and good answers to these tough interview questions will reveal how well they match your company. 

Story-based questions can yield particularly valuable results. Consider asking applicants the following:

“Tell me about a time you’ve disagreed with a superior. How did you handle it?”

These questions are difficult to answer but will probably elicit answers that are real and unrehearsed.

Difficult behavioral interview questions and answers are another great category you should use in interviews.

A question like “Have you ever chosen to act outside your company’s normal policy?” will tell you much more about a candidate’s personality traits, interpersonal skills, and motivators than common questions like “What are your strengths?”

Keep in mind that there are certain risks involved with asking difficult questions:

  1. Sometimes, overly assertive or aggressive questions can come off as dominating, which may make the interviewee feel that they are being interrogated more than interviewed.

  2. Catching someone off guard isn’t always ideal and may leave a stellar candidate speechless.

  3. There are also some boundaries you should respect, such as personal information. Most organizations have rules about asking deeply personal questions.

Consider that not every hard question has a place in an interview, and you have to make sure you identify and respect boundaries. Take your time building your collection of questions, and form them into a structured interview so that you’ll ask all of your candidates the same questions and eliminate bias.

Need help creating a structured interview? Take a look at our structured interview guide template.

Examples of tough interview questions to ask candidates

Let’s examine a few examples of questions, answers, and follow-up questions you can use for your next interview.

Follow-up questions will help you initiate a valuable discussion, giving you even more information and building a relationship with the applicant. These could be simple questions like “Would you do anything differently if it happened again?”

Tough interview questions and answers can be sorted into five categories:

categories of tough interview questions to ask candidates

We won’t be discussing the most clichéd questions, like:

  • What’s your biggest weakness?

  • Where do you see yourself in five years?

  • What are your career goals?

We’ll avoid these kinds of typical questions because they don’t reveal the meaningful information you need, and most candidates will have an answer planned.

examples of tough interview questions to ask candidates

1. Self-evaluation questions

These are questions that give you insight into what the candidate thinks about themselves or their level of self-awareness.

Are they overly confident? Are they uncertain?

You aren’t looking for someone arrogant, but it’s also good to make sure a candidate doesn’t sell themselves short.

Statistics show that 76% of recruiters reject people who are too arrogant, but 40% of interviewers won’t take a candidate to the next stage if they aren’t confident enough.  It’s clear that balance is key.

arrogance vs lack of confidence

Here are a few example questions for self-evaluation:

  • Think of a colleague you didn’t jibe with in your previous job. How do you think that person would describe you?

  • What three things have you done well in your last job?

  • What motivates you after failure?

The first question will tell you more than the typical interview question “What’s your greatest weakness?” This is because it asks the candidate what they feel others think of them, which encourages more self-reflection.

You’re more likely to get a more informative answer, such as “They’d probably say I’m a bit too finicky with my work and hold others up to the same standard,” rather than something crafted and rehearsed.

The third question is another upgrade from a standard interview question. Instead of just asking about candidates’ motivations, you’re specifically asking how they regain their motivation after taking a blow.

Knowing a candidate’s key motivators is crucial. It tells you whether or not their preferences align with the job you’re offering, and a strong match is connected to better performance and retention.

Try incorporating TestGorilla’s Motivation test into the skill assessment portion of your open job position to determine applicants’ baseline of motivation before the interview starts.

2. Personality questions

Personality-based questions are similar to self-evaluation questions but reveal more about a candidate’s actual traits and character rather than how they view themselves.

Story-based questions are great because the scene, atmosphere, and results of the story will tell you a lot about a person’s personality.

Here are some specific examples:

  • Have you ever disagreed with a supervisor’s directives? How did you handle it?

  • Tell me about a time when you lost your temper on the job.

  • How long are you willing to get something wrong before you get it right?

The second question has a lot of nuance to it. Everyone loses their temper at some point. It’s how you handle the situation that makes the difference.

You can learn a lot about an individual’s personality from how they deal with anger.

The last question will also reveal a lot about your candidate. You don’t want to hear either extreme end of the spectrum – that they always fail or always succeed. You want to hear an honest, human response. Here is a good sample answer:

“Failure will happen. I’m willing to get something wrong once or twice, but the key factor is learning from it.”

Too many candidates try to answer these types of questions by claiming that they never fail. Since that isn’t possible, it reveals something about their character. Red flag!

You can get a head start on understanding a candidate’s personality before the interview by incorporating any of TestGorilla’s personality and culture tests into your pre-employment process.

3. Experience questions

These questions deal with past situations and how candidates handled them. 

You can use these questions to discover more about an individual’s methodology, critical-thinking abilities, and interactions with other workers.

Role-specific questions are useful in this line of questioning because the answers you get will provide insight into how they would react to situations they might encounter in the position you’re offering.

Some example experience questions for a few different roles include:

  • Project management: Has a client ever asked for something outside the project’s scope? How did you react?

  • Content marketing: Have you ever received a complaint about the quality of your work from a client? What did you do?

  • Customer service: Has a customer ever yelled or sworn at you? How did you respond?

The first question will give you an idea of how a project manager reacts to helicopter clients.

You want a project manager who is courteous to the client but doesn’t say yes to every whim. Boundaries are healthy, and being unable to set them could be detrimental to your business.

The second question gives you vital information on how a candidate deals with negative feedback from a client. You want someone who can take criticism and turn it into something positive.

Experience-based questions like the third question are beneficial when interviewing for customer service roles.

Assessing how a customer service representative reacts and responds to customers is crucial. Customers can get emotional, whether they become angry or confused. Being able to talk through these kinds of situations calmly is part of the job description.

For more on this, take a look at our blog article on customer service interview questions.

4. Values questions

These questions dive into an individual’s values and principles.

What does the candidate consider important? What do they respect? 

Knowing your candidate’s values helps you understand them. Their values show you if the person is a good culture add. 

Incorporate our Culture Add test into your pre-employment assessments to get a basic idea of a candidate’s values, and then use value-driven questions to find the perfect fit.

Here are a few example questions:

  • Give me an example of a time you were part of a great team.

  • Can you share a story that demonstrates the values you hold?

  • Tell me about a difficult environment you’ve worked in. Why was it difficult, and how did you handle it?

  • Have your morals ever been challenged? What did you do?

  • Why are you looking for a new job? (Or, Why are you leaving your current job?)

  • What’s the first thing you look for when job searching?

Let’s take a quick look at a few potential follow-up questions that will initiate further discussion:



1. Can you tell me about a time you put your work aside to help a team member?

How did that turn out?

2. Has your work ever collided with your ethics? How did you handle it?

Would you have done anything differently?

Digging deeper with follow-up questions will lead to a more in-depth, nuanced conversation. Let’s examine the follow-up to the first question and a few examples of answers candidates could give you:

  1. “It turns out I put aside too much time. I didn’t finish my work on time, so I suppose I shouldn’t have helped my teammate.”

  2. “I had to prioritize parts of my work to get it done in time, but I managed to complete it just fine.”

Being a team player is important, but it poses a problem if it’s at the cost of productivity and efficiency.

Combining value-based questioning with follow-up questions will give you deeper insights that you can use to make a well-informed decision.

5. Competency questions

Now, it’s time to explore an individual’s capability and knowledge.

These questions give you an idea of a candidate’s overall competency and reveal different aspects of their work history. 

The number of jobs requiring analytical and social skills has increased by 94% since 1980, so assessing a candidate’s cognitive competency is imperative.

Let’s look at a few example questions:

  • What do you do when priorities or projects change suddenly?

  • Describe a time when you had to manage an underperforming team member.

  • Have you ever mentored a junior colleague? What career advice did you give?

  • How do you keep your job knowledge current with industry changes?

The first question provides insight into the applicant’s decision-making and problem-solving skills. You’ll want an answer that shows that the person is decisive and applies critical thinking to solve problems.

The second and third questions reveal the candidate’s leadership and communication skills.

Question four tells you how much a candidate values learning and professional development. Researching and staying up to date with new developments in the industry is an important skill that is often overlooked.

Integrating tests like our Communication test, Problem Solving test, and Attention to Detail test into your hiring process will give you a preliminary glance at a candidate’s competency, as well as ideas for the interview.

Flipping the script: how to answer tough interview questions from candidates

Who’s interviewing whom?

A candidate asking you questions can be a great thing. It shows they have experience, interest in the position and organization, and leadership skills, among other things.

Recruiters agree that curiosity is a good thing since 47% of job seekers fail their interviews because they do not know enough about the position and company.

Asking the interviewer tough questions may seem a bit forthright – because it is. However, this isn’t necessarily a bad thing.

Candidates asking questions helps you:

  1. Learn what the candidate finds important or exciting about the business and position

  2. Identify prepared and motivated candidates

  3. Take an opportunity to describe your organization and promote its benefits

We’ll discuss a few points on how you can prepare for these conversations so that you can:

  • Provide an honest answer

  • Describe your company culture and the job responsibilities

  • Provide context about the organization (hires often happen after someone has left, which they may not have done on good terms)

  • Remain professional and respectful

  • Maintain the line between vulnerability and oversharing

Let’s look at how to answer tough interview questions from the recruiter’s point of view.

how to answer tough interview questions from candidates

Prepare for tough questions with your team

Take some time to identify possible tough questions. Consider questions about why the position is empty, employee satisfaction, job responsibilities, company controversy, and more.

Discuss these questions with your team to get other opinions on potential questions and answers.

Teammates will be able to provide another perspective. For example, they could help explain a recent issue in your industry, like the latest Google algorithm update and how it affects your business. 

It’s advantageous to discuss these possible future questions with teammates, who can also join you in the interview room or video call.

This leads us to the next point.

Have someone else present at the interview

Having another team member present during the interview provides excellent support – you’ll have one more person to assist you in giving good answers to tough interview questions.

This teammate can provide additional insight and answers to your prospective candidate, which will better inform them and prevent you from stuttering or being at a loss for words.

Identify and hold boundaries

Just as the candidate is allowed to maintain boundaries, so are you.

Identify boundaries for your business and hold them. Transparency is respectable and encouraged, but that doesn’t mean you need to disclose every process and report fully.

Some subjects simply can’t be discussed in an interview for legal and ethical reasons.

You aren’t allowed to ask about applicants’ marital status or race, and the candidate isn’t allowed to ask about certain company policies. The information you shouldn’t discuss will vary between organizations but could include past clients and anything surrounding a non-disclosure agreement.

It’s best to research your business and local privacy laws to identify company information you’re not allowed to discuss with a candidate. Additionally, look into which questions you aren’t allowed to ask candidates.

Research your organization’s processes

Knowing key company information is imperative to learning how to answer tough interview questions.

Some questions could leave you speechless, such as:

  • What’s your monthly burn rate?

  • What’s your net revenue retention?

  • What’s your reliance on venture capital funds?

Researching your organization’s processes, history, and practices thoroughly will prepare you for hard-hitting questions. You want to be ready for these because the star candidates are the ones who tend to ask these difficult interview questions.

Know the role you’re offering and what you expect from candidates

A great candidate will show curiosity about the position. They’re bound to ask questions like:

  • What goals do you expect me to accomplish in the first 90 days?

  • How long does it typically take for a new hire to become a regular employee with benefits?

  • Are there any examples of a career path that starts with this position?

Knowing the ins and outs of the position you’re offering enables you to provide more actionable information to the candidate and strengthens your credibility.

Know your company’s background

Exploring your company’s background is key to taking your interview to the next level.

The toughest questions will be about allegations, layoffs, unhappy past employees, and reviews on websites like Glassdoor:

  • What happened to the previous employee? 

  • Was the previous worker fired, or did they quit?

  • Is this a new position?

  • Have you ever had a round of layoffs?

  • Why do you only have three stars on Glassdoor?

If the candidate has done their research, they’ll want to talk about your business. 

Knowing your organization’s background will also ensure you can converse about anything positive the candidate brings up, such as recent successes or events.

Be transparent where you can

“If you tell the truth, you don’t have to remember anything.”

Mark Twain said that – and in almost every circumstance, it’s 100% true.

As we discussed earlier, you can’t be fully transparent about everything. However, being honest about your business, your culture, and the position is ideal.

This will help a candidate to understand what to expect and determine if they’ll be a good fit, which is something you both want.

Candidates don’t want to seek employment elsewhere after onboarding for three months – and you don’t want to restart the hiring process.

Remember that it’s a good thing when candidates give tough questions and answers during the interview. It’s more of a concern when they have nothing to say and zero curiosity.

Get the right candidates to the interview stage with bias-free testing

It’s crucial to know how to ask and answer tough interview questions.

Delving into a candidate’s personality, experience, and values will tell you much more than asking typical questions like “Tell me about yourself.”

Your questions will be more impactful, and you’ll learn even more about a candidate if you implement skills-based pre-employment assessments before the interview. 

Improve your interview process by removing CV screening and relying on tests that assess skills, situational judgment, and cognitive abilities. This way, you’ll be asking tough yet relevant and fair questions before the interview even starts.

Create a free TestGorilla account to get access to bias-free pre-employment testing.


1. Boskamp, Elsie. (April 5, 2022). “39 Important Job Interview Statistics [2022]: What You Need to Know Before Starting Your Job Search”. Zippia. Retrieved August 15, 2022.


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