Discussion Questions


  1. Where do you see yourself in 5 years?
  2. If you could have any other career than your current career what would it be? Why?
  3. As a kid, what did you want to be when you grow up?
  4. Why and how did you get into your current career?
  5. What’s the most important thing you need from an employee?
  6. What’s the best thing you can give your employer?
  7. When was your last vacation? Where did you go? What did you do? Who did you go with? Why did you choose that destination/activity?
  8. When is your next vacation? Where will you go? What will you do? Who will you go with? Why did you choose that destination/activity?
  9. Do you have a hobby? What is it?
  10. How does your hobby influence your business or business decisions?
  11. In the next 30 days what policy, procedure or process do you need to refine, replace or refresh in order to grow your business?
  12. How would you describe your approach to:
    1. Customers
    2. Employees
    3. Employer
    4. Family
    5. Friends
  13. What’s your favorite weekend activity?
  14. What about your career do you find most rewarding?
  15. What about your career do you find most draining?
  16. What need does your boss have that you could meet today?
  17. What need do your employees have that you could meet today?
  18. In your field, what sets you apart from your competition?
  19. In your field, what does the competition do better than you?
  20. Name your 5 most important relationships and why.
  21. Name your greatest strength:
    1. In your family
    2. In your business
    3. In the eyes of others
  22. What is your area of most needed improvement:
    1. In your family
    2. In your business
    3. In the eyes of others
  23. What’s one thing you can do today to accomplish the most important goal on your goals list?
  24. What’s one thing you keep doing that you absolutely must stop now?
  25. How does your belief about spiritual matters influence your life and business decisions?
  26. In your personal opinion what do you understand it takes for a person to go to heaven?
  27. Which is more important and why?
    1. Character or profit
    2. Family or friends
    3. Business relationships or personal relationships
    4. Having right fact or having right relationships?
  28. How much time do you spend each day day-dreaming?
    1. What do you day-dream about?
  29. How do you balance:
    1. Art and analysis?
    2. Creativity verses the familiar?
    3. Process and procedure verses getting the job done.
    4. Efficiency verses effectiveness?
  30. What’s the most important lesson you’ve ever learned?
    1. How did you learn it?
  31. If you could teach your star employee one thing today, what would it be?
  32. If you could teach your least effective employee one thing today, what would it be?
  33. When was the last time you expressed appreciation to your:
    1. Employees
    2. Employer
    3. Family
    4. How did you express that appreciation?
  34. When was the last time you disciplined someone in your organization?
    1. What did that look like?
    2. Is there anyone who needs correction today?
  35. How do you spend your time during an average workday?
  36. Name one product that has changed the way you do business.
    1. How did it change your approach to business?
  37. Who is currently the most influential person in your life?
    1. Why?
    2. How have they influenced you?
  38. What is your biggest pet peeve?
    1. In business
    2. In family
    3. In friendships
    4. In general
  39. What fills your tank?
  40. What drains your tank?’
  41. What do you consider your greatest success?
  42. What do you consider your greatest failure?



  1. Name your favorite (and why):
    1. Super Hero
    2. TV Show
    3. Movie
    4. Song
    5. Artist – music or otherwise
    6. Person living today
    7. Person in history
    8. Candy bar
    9. Soft drink
    10. Food
    11. This list could go on and on…
  2. If you could have any super power at all, what would it be?
  3. Are you a cat person or dog person and why?
  4. Which is better:
    1. Cats or Dogs?
    2. Sooners or Cowboys?
    3. Ice Cream or Cake?
    4. Movies or Books?
    5. Career or Personal Life?
    6. Men or Women?
    7. Old or Young?
    8. New or Classic?
    9. Ginger or Mary Ann?
    10. This list could go on and on…
  5. Name your favorite local restaurant.
  6. Name your least favorite local restaurant.
  7. Name one thing the city could do today that would improve the quality of life in this place.
  8. What’s the most romantic thing you’ve ever done?
  9. Tell us your most embarrassing moment.
  10. What’s the strangest thing you’ve ever eaten?
  11. What’s the craziest thing you’ve ever done?
  12. If your life were a television show, what would it be called?
    1. What kind of show is it? Sitcom, Comedy, Drama, Reality, etc…
  13. Quote the lyrics to your favorite song – see who can guess the name, artist, album and year.
  14. You’re stuck in an elevator:
    1. What’s one thing you absolutely hope you have with you?
    2. Who is the one person you hope to have with you?
    3. Who is the one person you hope is not in the elevator with you?
  15. What exactly is Victoria’s Secret?
  16. If you could invent a new buzz or cuss word what would it be? Use it in a sentence.
  17. Which cartoon character do you most relate to?
  18. In the movie of your life, which actor do you hope plays you?
  19. Would you willingly reduce your expected life span by 5 years to become more attractive/successful/powerful/rich/etc…
    1. Keep increasing/decreasing the number till you find someone’s price.
    2. VARIATION: Ask, “Would do this for $XXX?” Find someone’s price.
  20. You’re on death row:
    1. Why are you there?
    2. What’s your last meal?
    3. Who’s the last person you want to talk with?
    4. Are you innocent or guilty?
  21. You’ve joined the circus, what’s your act and circus name?
  22. What’s your name?
    1. Rap Name
    2. Country Name
    3. Porn Name
    4. Rock Star Name
    5. Uptight Accountant Name
  23. GROUND HOG DAY – You have to repeat the same day over and over again till you get something right. What’s the one thing you keep getting wrong that you get to make right this Ground Hog Day?
  24. Under what conditions would you perjure yourself for a friend?
  25. Under what conditions would you turn your friend/coworker/employer/employee/spouse/family member in for a crime?
  26. What does financial independence mean to you?
  27. What is your first memory about money?
  28. What is your first memory?
  29. How old were you when (ask for details):
    1. First kiss
    2. First failure
    3. First job
    4. First real success
    5. First heartbreak
    6. Knew this was the career for you
  30. Name one thing you would like to change about yourself.
  31. What’s the funniest joke you know?
  32. What’s the worst joke you know?
  33. What thought or message would you put inside a fortune cookie?
  34. Growing up, what where your favorite toys?
  35. Growing up, what did you want to be?
    1. When did you give up on this dream?
  36. What award would you love to win?
  37. If you could add one person to Mount Rushmore, who would it be?
  38. If you could have your face on any piece of currency, which currency would you choose?
  39. You just won the lottery. You’re set for life.
    1. Do you continue in your current career?
    2. What’s the first thing you buy?
    3. Do you keep it all or give some of it away? How much?
  40. If you had a time machine where/when would you go?
  41. What is one thing you should probably throw away, but probably never will?
  42. What is the meaning of life, the universe and everything?


  1. Can you name a person who has had a tremendous impact on you as a leader? Maybe some one who has been a mentor to you? Why and how did this person impact your life?
  2. What are the most important decisions you make as a leader of your organization?
  3. As an organization gets larger there can be a tendency for the “institution” to dampen the “inspiration.” How do you keep this from happening?
  4. How do you encourage creative thinking within your organization?
  5. Where do the great ideas come from in your organization?
  6. Which is most important to your organization—mission, core values or vision?
  7. How do you or other leaders in your organization communicate the “core values”?
  8. How do you encourage others in your organization to communicate the “core values”?
  9. Do you set aside specific times to cast vision to your employees and other leaders?
  10. How do you ensure the your organization and its activities are aligned with your “core values”?
  11. How do you help a new employee understand the culture of your organization?
  12. When faced with two equally-qualified candidates, how do you determine whom to hire?
  13. What is one characteristic that you believe every leader should possess?
  14. What is the biggest challenge facing leaders today?
  15. What is one mistake you witness leaders making more frequently than others?
  16. What is the one behavior or trait that you have seen derail more leaders’ careers?
  17. Can you explain the impact, if any, that social networking and Web 2.0 has made on your organization or you personally?
  18. What are a few resources you would recommend to someone looking to gain insight into becoming a better leader?
  19. What advice would you give someone going into a leadership position for the first time?
  20. What are you doing to ensure you continue to grow and develop as a leader?
  21. If you had to develop a brand-new course to be taught in colleges, what would it be?
  22. If you could erect a lighthouse that would guide all human beings toward one particular virtue, which virtue would it be?
  23. When you were a child, what job did you most want to have when you grew up?Which of the seven dwarfs personifies you best—Dopey, Sneezy, Sleepy, Bashful, Grumpy, Happy, or Doc?
  24. If you could bring back any tradition that seems to have faded into the past, what tradition would you bring back?
  25. In hindsight, what particular class in school, at any level, above all others do you wish you had paid more attention to or taken more seriously and why?
  26. What is the greatest lesson you’ve learned in life thus far?
  27. What fear do you most want to be rid of forever?
  28. You are offered an envelope that you know contains $50. You are then told that you may either keep it or exchange it for another envelope that may contain $500 or may be empty. Do you keep the first envelope or do you take your chances with the second?
  29. Where do you turn for tough decisions? Why?
  30. If you could eliminate one month on the calendar, going directly from the month preceding it to the month following it, which month would it be?
  31. If you could wake up tomorrow morning fluent in any language, which language would you choose?