How To Answer the Most Difficult Interview Questions

Job interview
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You’re bound to be asked some difficult questions any time you interview for a new job. Although you can’t know which challenging questions will come up, there are several common possibilities. It’s wise to practice answering tough questions during your interview prep.

Review sample questions and consider what responses might be appropriate, based on your background, skills, and the job opportunity. 

There aren't necessarily any right or wrong answers, but you will need to consider the job requirements you are applying for, your strengths, and the company culture before you respond.


Becoming familiar with the popular question categories and some questions that are in them can help you have better results for your next interview.

Questions About Co-Workers and Supervisors

Interviewers will ask about your experiences with your colleagues and managers to determine how well you will fit in with a particular group. Try to keep a positive spin on all your answers, even when there is the temptation to criticize someone you worked with. 

Here are some examples:

  • Tell me about a time when you had to deal with a co-worker who wasn't doing their fair share of the work. What did you do and what was the outcome?
  • Give me an example of when you took the time to share a co-worker's or supervisor's achievements with others.
  • Tell me about a time that you didn't work well with a supervisor. What was the outcome and how would you like to have changed what happened?
  • Have you worked with someone you didn't like? If so, how did you handle it?
  • Tell me about a time that you helped someone.
  • Tell me about a time that you misjudged a person.
  • How do you get along with older (younger) co-workers?

How to Respond 

When it comes to answering questions about bosses, aim to keep it positive. (Yes, that's true even if you had a frustrating or despised supervisor or colleague.) You'll want to stay away from personal insults, along with negative comments or complaints. 

If you didn't get along well with a manager, look for opportunities to frame your answers to questions about supervisors in terms of what you've learned or how you've grown.

For questions about co-workers, strive to display your ability to work well with a team. 

Questions About Your Abilities

The hiring manager will be assessing your abilities during your interview so they can try to determine how successful you might be in the position you’re seeking. It would help if you thought about specific examples of positive outcomes from previous jobs. Here are some example questions:

  • Describe a decision you made that was a failure. What happened and why?
  • Tell me about a time that you needed to convey technical information to a non-technical audience.
  • Tell me about a time that you worked interpreting and presenting data.
  • Why do you think you will be successful in this job?
  • Tell me about a time that you participated in a team. What was your role and how well do you think you fulfilled it?
  • Tell me about a time when you faced conflicting priorities. How did you determine the top priority?
  • Tell me about a time when you failed.

How to Respond

As you answer questions about your abilities, focus on sharing your most relevant hard and soft skills. Both matter! Both the job advertisement and the interview itself can offer cues as to the skills that will be most in demand by hiring managers for this role.

Questions About Yourself

It’s appropriate for hiring managers to ask some personal questions during an interview, as long as they are professional and relate to your ability to do the job. Consider these questions:

  • What would you do differently if you could start your working life over?
  • How do you balance life and work?
  • What is your preferred way to communicate—instant message, phone, or email?
  • Do you check voicemail and email when on vacation?
  • What is your favorite book? How about your favorite movie?
  • What historical figure do you admire and why?
  • If you could choose anyone (alive or deceased) to have lunch with, who would it be?
  • What did you do during this six-month gap in employment?
  • What do you love to do for fun?
  • What led you to this point in your life?
  • Do you consider yourself successful?
  • What inspires you in a job?
  • What excites you most about the position and what do you think would be a stretch for you?
  • Who are the influencers in your life?

How to Respond

People spend many hours at work, so it's only natural that hiring managers will ask questions about you during interviews

In your replies to these questions, be honest but strategic – for instance, maybe what inspires you in a job is a paycheck, but that's the kind of response that will make an employer hesitate about hiring someone. If you were faced with this question, try to think of a non-financial inspiration that reflects well on you as an employee. 

Plus, look for ways that your responses can show you have the background, personality, and skills the employer is looking for in the role at hand. 

Questions About Your Career Goals

When the interviewer asks you about your career goals, you’ll want to convey your ambition for the future and stress your interest in learning and growing in the opportunity. Your interviewer may want you to start with your college graduation and explain the rationale behind each of your career moves. Also, they may ask you to explain the thinking process that went into making each of those decisions. They might also ask:

  • How many hours a day/week do you need to work to get the job done?
  • If you stayed with your current company, what would be your next move?
  • How do you measure success?
  • Describe your dream job.
  • Describe a job that would be your worst nightmare.
  • If you were the CEO of this company, what would be the top two things you would do?

How to Respond

This is one area where preparation and self-knowledge help. 

If you have thought previously about your long-term career goals, answering questions about career goals is relatively easy. But if you've never considered the role you hope to have in five years, for instance, providing an answer can be quite challenging.

To respond, try thinking about your short-term goals first, and then expanding out into the future. You can focus on the steps you'll take to hit your longer-term goals. 

Questions About Working With Other People

In any position, interaction with your colleagues is essential, and how well you manage your relationships with others impacts the work environment for everyone. Interviewers will ask questions to determine how well you can work with others. For example:

  • How would you assess the skills, personality traits and work ethic of candidates by applying behavioral interviewing techniques?
  • What techniques have you used to motivate subordinates to improve performance?
  • Are you comfortable leading group discussions in a way that incorporates diverse views and draws consensus?
  • How do you develop a comfortable rapport with clients and determine their preferences for products and services?
  • Do you listen actively and empathetically to encourage clients to share their feelings and problems?
  • Have you created and delivered training sessions that engage the audience in active learning? Please describe.
  • How would you break difficult news to an employee targeted for layoff?
  • Tell me about a time when you mediated conflicts between employees or with clients.
  • Are you able to resolve customer complaints with patience and creativity?

How to Respond

Nearly every job out there requires working with others, whether it's teammates or clients. In your response, consider giving examples from previous work experience. This is also an opportunity to discuss your people and communication skills. 

More Challenging (and Some Strange) Questions

These questions don’t fall into any particular category, and they may seem a bit unnerving. But they’re worth considering:

  • Are you a risk-taker?
  • If you were an animal, what would you be?
  • Convince me to hire you.
  • We unplugged that clock on the wall. Why did we do that?
  • Why shouldn't I hire you?
  • What does your current employer think you are doing today?

How to Respond

These types of oddball questions are generally designed to throw you off guard. Some interviewers will be eager to see how you respond when you're surprised or even a bit uncomfortable. You can pause and acknowledge that in your response as a first step. You might say, "Wow, that's a new one!" or "Hmm, I hadn't thought of that before." Then, do your best to gather your thoughts and give a thoughtful response. 

Interview Questions Employers Should Not Ask

Some of the most challenging interview questions shouldn’t be asked at all. These include questions about age, race or nationality, pregnancy, disability, marital status, and religion.

These kinds of questions are generally against the law, and employers should not ask them during a job interview. But, from time to time, hiring managers slip up and ask questions they shouldn’t. 

It pays to be prepared to handle unethical or inappropriate questions so that you’ll know what to do. Depending on the situation, you might choose to end the interview, refuse to answer or answer politely while avoiding the question's illegal part.

Key Takeaways

  • Tough questions are designed to make you think and create responses on the spot—it helps to have situations in mind before the interview.
  • It helps to practice answering difficult interview questions and have situations that you can discuss.
  • Preparing for some very strange questions can help you not appear shocked or off-guard.
  • Knowing the topics employers cannot ask you about can help you avoid or answer them tactfully.

Article Sources

  1. CareerOneStop. "Illegal Interview Questions."