Smart businesswoman asking question
ATD Blog

12 Tricky Interview Questions—and How to Answer Them

Friday, April 23, 2021

Sign up for the My Career Newsletter!

Yes, it's important to craft a strong, accurate résumé and cover letter. But like it or not, most jobs are secured or lost during the interview. While there are no perfect answers, some forethought about how to address potentially tricky interview questions and deliver great answers to them can help you avoid disaster. Here are 12 common yet tough interview questions that tend to trip up even the best candidates—and how to answer them to your advantage. 

1. What Is Your Greatest Strength? Before interviewing (or even your job search), reflect on your personal strengths and make a list of them ("natural number sense," "able to multitask," "good with people," "able to teach others"). Then tie each of these strengths to a professional accomplishment. Answer with the strength you feel best fits the position being discussed, and be sure to offer the anecdote that goes with it. Conclude your response by asking the interviewer if this is the kind of quality that would help his or her company.  With all of your responses, strive to keep your answers to 60 seconds or less so that your interviewer's attention doesn't wane.

2. What Is Your Biggest Weakness? As with your strengths, prepare a list of weaknesses beforehand. This time, tie each weakness back to what could also be considered a strength. For example, "I like to get things done. Sometimes I get impatient, but I'm getting a handle on it." Or maybe you have actually come up with a way to mitigate your weakness: "I'm a stickler for details, but I do not want to be a micro-manager. So at my last job, I asked each staff member to devise their own checklist of weekly tasks. It gave them some autonomy and satisfied my desire for quality control."

3. Can You Work Under Pressure? This question could be revealing some red flags about what kind of work environment there is, so dig deeper with your own questioning. Ask the interviewer how much pressure is involved in the position. Learn what the interviewer means by "pressure." The definition can vary significantly from person to person and company to company. If you are a pro at high-pressure jobs, describe a few accomplishments and show that you can handle stressful situations.

4. What Did You Think of Your Last Manager? Whatever your true feelings might be, stay positive. This is not the time or place to list your boss's shortcomings or frustrating behaviors. Try responses like: "She was the kind of person I could learn from." or "We were able to communicate well and things got done quickly."

5. What Motivates You? Resist the temptation to joke, "A steady paycheck!" Tie your motivation to the work being performed at this specific company. In addition, you could mention things like the opportunity to learn and grow, working with smart people who are passionate about their jobs, and contributing to the success of an organization.


6. What Do You Not Like to Do? This is a loaded question. A positive reply might be, "I'm the kind of person who does whatever is necessary to get the job done. When I do run into something disagreeable, I try to do it first and get it behind me. I have no particular dislikes."

7. How Would Your Boss, Co-Workers, and Subordinates Describe You? Be ready to give some examples of the kind of team player you are. If you are not into office politics and have harbored good relationships at work, mention it. And remember that the interviewer may ask your references the same question. I strongly suggest contacting your references before the interview stage in order to talk through your career goals and how the reference can best support them.

8. What Has Been Your Biggest Failure? Discuss this question with friends, mentors, and possibly your references before the interview. If at all possible, think of something you were later able to correct. Then the story isn't just about a failure, but also about a learning experience.

9. How Do You Feel About the Progress You Made in Your Last Position? Don’t discuss your feelings, per se, but do stress your accomplishments. For instance, "When I started with the Blake Company, I was given responsibility for their operations in Mexico and Costa Rica. After I turned them around, they made me general manager for Mexico and Central America. How are your international operations performing?" An answer like this communicates great information about your value as an employee while still conveying positive feelings about your progress.


10. Did You Have Any Frustrations in Your Past Job? Frustrations are a normal part of any job, and interviewers know this—so don't claim you didn't have any. Relate some of the bottlenecks you experienced and show off your problem-solving skills here by indicating what you did to overcome these frustrations.

11. Why Do You Want to Work for Our Company? Your reply could be based on their reputation for products, management, international scope, technology, or as a nice place to work and grow. The most important thing is to avoid generic answers. Know their products, policies, and potential for growth.

12. Why Should We Hire You? If you know the job requirements and can match them with some accomplishments, briefly share those anecdotes. Say, "If there are opportunities to do that and more here, then this is a great fit." What an employer wants to hear is that you are an easy fit with their company and for the role.

You may not be asked these specific difficult interview questions, but knowing how you want to answer them will ensure that you're prepared to discuss a wide variety of topics. Indeed, you don't want to have to formulate complicated answers in the midst of an already nerve-wracking situation.

Check out similar articles: Beat the Resume Bots and Win That New Job
ATD Members can learn how to write a winning resume with this micro-course.

This blog was originally published in March 2015 and has since been updated with new resources and information.

About the Author

Peter K. Studner is the author of Super Job Search IV: The Complete Manual for Job Seekers & Career Changers. He is a master career counselor and former chief executive and board member of companies in the United States, France, and Great Britain. He has helped thousands of people with their career transitions and trains other career professionals to deliver this easy-to-follow program. To learn more, please visit

Be the first to comment
Sign In to Post a Comment
Sorry! Something went wrong on our end. Please try again later.