Conversation Questions about Careers

Discuss and ponder your career path and those of your loved ones using our comprehensive list of career questions!

Delve into topics such as skill enhancement, career goals, networking strategies, and personal fulfillment to gain clarity and direction in your career journey.

  1. What do you think you do better than 90% of people?
  2. What were some early life experiences that hinted at what you might be good at professionally?
  3. Who are three people on your personal Board of Directors (I.e. people who you go to for career advice)?
  4. In what job or role were you at your best thus far in your career?
  5. How many hours per week do you work? How many hours a week do you generally SAY you work?
  6. What is your most controversial career opinion?
  7. Have you ever experienced a career setback?
  8. If you had to start a company today what would it be?
  9. Do you think you are more or less intelligent than most people on your current team?
  10. What company do you despise?
  11. If you had to give a TedTalk today what would it be on?
  12. What job do you wish paid more?
  13. If you had a magic wand, what is the one thing you would change about the organization you work for right now?
  14. What is the best idea you have ever had for a business?
  15. If you absolutely had to do it, what book would you write?
  16. What is the best advice you have ever received? What is the worst advice you have ever received?
  17. What percentage of your co-workers do you get along with?
  18. What qualities do you look for in a boss or manager?
  19. What does your family think of your career?
  20. What’s the worst piece of advice you’ve ever given?
  21. What’s the coolest project you’ve ever worked on?