Twenty Difficult Interview Questions and How to Answer Them

Answering Interview Questions:

Twenty Difficult Interview Questions and How to Answer Them

Prepare yourself for answering interview questions by taking the time review this more difficult interview questions below. These questions, along with other typical interview questions, career and career change advice we've gathered for you on this site will help you to prepare for your next interview.

Write out your answers to the sample interview questions below using the free interview answers notes as a guide. Then edit, revise and study them so that when the time comes, you easily make connections and articulate meaningful insights.

When you are answering interview questions, structure your answers in what has become known as the STAR method. STAR stands for:

Situation or Task
Action you took
Results you achieved
If you include those key components in your answers, the conversation will easily flow and you will naturally provide the detail and results that set you apart as a thoughtful, articulate applicant.



Tell me about yourself.

Answer with a quick overview of who you are and why you’re the best candidate for the job. An expanded 30-second commercial is a great way to start. Feel free to expand on relevant items (such as your key strengths), up to two minutes total. Sell yourself.


Why did you leave your last position? / Why are you leaving your current position?

This is critical: When answering interview questions, don’t "bad mouth" a previous employer or come off opportunistic. Be brief and to the point. Be clear, particularly if you were involved with a layoff, buy-out, shutdown or other company change. If you are leaving on your own or have left a position, describe the change in a positive way. Perhaps your chance to make a contribution has changed. Money should not be part of this discussion.


Tell me about your most significant accomplishment.

This will highlight your greatest strengths and could get you the job, so prepare extensively. Tell a two-minute story with details and discuss personal involvement. Demonstrate how the accomplishment you describe was worth achieving. Discuss hard work, pressure, long hours and the important company issues that were at stake.


Why should we hire you?

When answering interview questions like this, pick two or three main components of the job and about you that are most relevant. Discuss for two minutes, with specific supporting examples. Be enthusiastic!


Tell me about a time when you accomplished something you didn’t think you could?

When answering interview questions like this, you have the opportunity to demonstrate that you are not a quitter, and that you’ll get going when the going gets tough. The interviewer is trying to determine your approach, work ethic and personal commitment. Provide a solid example that describes a situation when you overcame numerous difficulties to succeed.


Tell me about a time when you had to take the initiative to get something done.

Use a series of short examples that showcase your personal motivation. Proactive, results-oriented people do not have to be told what to do. Describe at least one example in detail. Demonstrate how you make the extra effort, have a strong work ethic and are a creative problem solver.


What do you like or dislike most about your current position?

Be smart about answering interview questions like this. Stating that you dislike overtime or details or some other essential to any job might cost you the position. There is nothing wrong with liking challenges, pressure situations, opportunities to grow, or disliking bureaucracy and frustrating situations. If you can show how you made a difference overcoming something you did not like, all the better!


Tell me about a time when you had to be effective in a high-pressure situation.

If you perform well under stress, provide a strong example with enough detail that allows the interviewer “feel” the stress. High achievers tend to perform well in high-pressure situations. This may be an area for you to probe more deeply at the appropriate time, the question could imply the position is pressure packed and out of control. There is nothing wrong with this as long as you know what you’re going into.


Tell me about a time when you made a mistake or did something that you would approach differently if you had a second chance.

This question probes whether or not you can learn from your mistakes. If you can, it indicates that you have an open, more flexible personality. Highlight a failure or challenge if you’ve learned from them. This is an important aspect of high potential individuals.


What are your strong points?

When answering interview questions like this, be prepared to describe specific characteristics and how they have proven critical to your success. Be able to discuss 4-5 strengths with a specific example for each. Highlight those attributes that are most compatible with the job opening. Be thoughtful and detailed here, it shows your personal awareness.


What are your weak points?

Focus here on tolerable faults that you are working towards improving; show by specific example how this has changed over time. Or, show how a weakness might be a strength that was carried too far. For instance, "I sometimes get impatient if a project is running behind schedule."


Tell me about a time when you had to persuade or influence someone to get something done.

The ability to persuade is common in many roles. This answer shows your approach. Find an example that demonstrates your ability focus on the needs of others and create a win-win situation that accomplishes your primary objective.


What do you know about this organization?

Put your research to work and describe at a high level the company’s products, revenues/size, history, philosophy, reputation, people and/or goals. However when answering interview questions like this, don’t act like you know it all, show that you are eager to learn more. Keep your discussion upbeat and positive.


What important trends do you see in the industry?

Again, put your research to work and be prepared with two or three trends that illustrate that you understand the opportunities and challenges. Consider covering economic conditions, competition, regulatory demands or other areas as necessary.


One of our biggest challenges is ____________? How would you approach this?

It is highly likely you have some experience with parts of this challenge so ask clarifying questions to get details and break the challenge into manageable parts. When answering interview questions like this, use your organizational and analytical skills to draw insights. If you cannot answer it directly, state how you would approach the problem.


Tell me about a time when you had to handle a situation under tight deadlines, low staff morale, and with minimal budget.

This will showcase your management skills. Relate your toughest management task, even if it doesn't meet all the criteria. Highlight your organizational skills, interpersonal skills and ability to act under pressure – these are important elements of effective management.


If you could start over, what would you change about your career up to this point?

Present yourself as a person who is happy with his or her life when answering interview questions like this. If there are things you would change, mention them. However overall it is important to convey that you have enjoyed the good things and learned from the rest. After all, it is the past that has prepared you for this position.


Where do you see yourself five years from now?

Be optimistic and realistic. If promotions are your goal, citing one or two management jumps in five years is reasonable. Or, you may opt to emphasize your contribution as in “being the best ___ you’ve ever had.”


How do you see yourself making a contribution to the organization in this position?

This is a good chance to summarize. Restate the key challenges of the organization and explain how you would address them. Relate back to your own past accomplishments. Be confident, yet humble through a thoughtful, organized and attitude that shows that you are willing to do what it takes to be successful.


Your resume suggests that you may more experience than this position calls for. What do you think?

Emphasize that you are interested in establishing a long-term association with the organization and that strong companies need strong staff when answering interview questions like this. Because you are so well qualified for the position, the company will benefit quickly. Let them know that you assume that if you perform well, new opportunities will open up for you over time.


Remember, writing out your answers to the sample interview questions here and using the free interview answers notes as a guide will dramatically improve your interview results. If you can master this list of interview questions and combine that strong research, you’ll be prepared to tackle just about any interview.

Good luck!