• Skip to content
MightyRecruiter MightyRecruiter
  • Solutions
    • Features
    • MightySourcer
    • Post free Jobs
    • Resume Database
    • Industries
  • Pricing
    • Software Pricing
    • Why Free ?
  • Resources
    • Blog
    • Customer Case Studies
    • Webinars
    • eBooks
    • Checklists and Infographics
    • Job Description Examples
  • Recruitment Guide
    • Legal
    • Business
    • Hiring
    • HR Glossary
  • Templates
    • Job Descriptions
    • Letter Samples
HomeRecruitment GuideHiring Tips for EmployersThe 50 Toughest Interview Questions
  • Legal Resources  
    • Termination Laws By State
    • Regular Laws
    • Wage and Hour Laws by State
  • Business Resources  
    • Business Closing
    • Business Finance
    • Business Tax
    • Starting a Business
    • Business Operations
    • Insurance and Liability
    • Intellectual Property
  • Hiring Resources  
    • Hiring Process
    • Wages and Benefits
    • Workplace Safety
    • Discrimination
    • Employee Termination
    • Managing Employees
    • Hiring Tips for Employers

The 50 Toughest Interview Questions

The 50 Toughest Interview Questions

Job interviews can be tough, both for the interviewer and the interviewee. While everyone has heard advice for job seekers, it’s also worth considering what the interviewer should be doing to prepare. One great way is by reading through the 50 toughest interview questions.

The questions you ask are a huge part of a successful interview, since they will help you determine whether or not a candidate is the best choice for your job. The 50 toughest interview questions listed here are important, because they let you see how the candidate reacts under pressure. They can also give you important insights into their thinking process and problem solving skills; some of these questions may even reveal important information that otherwise wouldn’t have come out. Keep the 50 toughest interview questions in mind next time you’re hiring:

The Questions

1.Why should we hire you

2.What could you do for us that someone else couldn’t

3.What are your strengths and weaknesses

4.Why do you want to work here

5.Are you looking for a job with any other companies Which ones

6.What do you know about our company

7.Why did you leave your last job (Or current job)

8.Why is there a gap in your employment record

9.Describe the worst boss you ever had.

10.Tell me one thing you would change about your last job.

11.How do you think your last boss would describe you Your coworkers

12.Have you ever had a supervisor question one of your decisions How did you handle it

13.Tell me about a time when you and your coworkers disagreed.

14.Have you ever been fired What where the circumstances

15.If you could live your life over again, what would you change

16.What have been your greatest accomplishments

17.Describe a difficult situation you’ve been through, and how you dealt with it.

18.What’s your personal definition of success

19.What are your goals for the next five years The next ten

20.What are you motivated by

21.Are you interested in management or leadership positions Why or why not

22.After money, what factor gives you the most job satisfaction

23.How do you perform under stress

24.Do you prefer to work alone or in groups

25.Do you prefer self-directed work, or clearly defined tasks

26.How would you feel about travel or relocation

27.How do you feel about drug testing

28.How do you feel about psychological testing

29.How do you feel about tying incentives closely to performance

30.How much are you expecting to earn

31.How long do you anticipate being with our organization

32.How many hours a week do you usually work

33.What would your ideal work environment be like

34.Describe your dream job.

35.Describe yourself in three words.

36.Do you consider yourself creative Give an example.

37.Do you consider yourself a traditionalist

38.Do you consider yourself a people person

39.Do you consider yourself a leader

40.What qualities do you think are necessary for leadership

41.Is it more important to be skillful, or lucky

42.Who are your role models Why

43.Describe a time when you took a courageous action or unpopular stand.

44.Tell me about the biggest risk you’ve ever taken.

45.If you started your own business, what would it be

46.Do you stay current in your field How so

47.Explain corporate insurance an eight-year old child. (Or public relations, or SEO, or data analysis, or any other complex subject your business handles)

48.How did you do in school

49.Is there anything else that you feel I should know about you

50.What questions do you have for me What would you like to know about the job or company

Reminders

Keep in mind that a few of the 50 toughest interview questions may need to be modified depending on the company and/or the individual candidate. For example, if you are hiring a recent college graduate, you might want to ask about their former professors instead of former bosses.

Also remember that job interviewers legally cannot ask about age, race, socioeconomic status, national or ethnic background, religion, veteran status, or disability.

Get Started

If you’ve prepared for the interview and considered the 50 toughest interview questions, then getting good people to fill your positions doesn’t have to be difficult. Check out the other tools and tips here on Mighty Recruiter to learn more about investing in great employees.

View All Hiring Tips

  • VIDEO TOUR
  • CHROME EXTENSION

MightyRecruiter

  • About Us
  • Work Here
  • Partners
  • Blog

Hiring Software

  • Features
  • Why Free?
  • Pricing
  • Free Job Postings
  • Free Job Description Samples
  • Watch Demo Video

Support

  • Terms of Use
  • Your Privacy
  • Disclaimer
  • Resources

Contact Us

Monday-Friday, 8am-5pm CST
1-844-382-1750
recruiterhelp@mightyrecruiter.com
Mighty Recruiter
  • Follow Us

© 2025, Bold Limited. All rights reserved

Powered by BOLD