100 Questions for Business Creativity

“A real conversation always contains an invitation. You are inviting another person to reveal herself or himself to you, to tell you who they are or what they want.” –David Whyte

As far back as I can remember, I’ve been what some would call “a deep thinker”. This can be both a blessing and a curse. A curse in that I can become obsessed with intellect and forget that the heart is the seat of true wisdom. A blessing in the sense that I ask family, friends and colleagues questions to strengthen our connection. Sometimes their answers reveal aspects of myself that are in need of healing. At other times, the answers provide a roadmap to witness dis-empowering belief systems and habits that keep me locked and loaded in perfectionism and feelings of unworthiness.

Recently, as I read a poem called “Sometimes” by David Whyte, it occurred to me that some of my questions may help another to become a witness to the thoughts behind their daily thoughts, intentions and actions. As we take a bold step into the new year, here are 100 questions to use for creative inspiration. With the right question, you may discover the solution to a problem or perhaps a bit of wisdom about yourself, your mindset, skillset, relationships, communication style, fears and passions. Who knows? The possibilities for good are endless!

100 Questions for Business Creativity:

  1. What lights up your soul?

  2. What did you enjoy doing as a child?

  3. What do people tell you that you do really well?

  4. What would you do with an extra $5,000?

  5. What are you dying to see in the world?

  6. What would your dream day look like?

  7. Who is your favorite live band?

  8. If you had unlimited time, what would you do with it?

  9. If you had to hire ten new employees, how would you grow your business?

  10. What was the best service ever performed for you?

  11. What do you day dream about?

  12. How are you helping the world and its problems?

  13. What was your favorite project in school?

  14. Who is your business role model?

  15. What advice do your friends always ask you for?

  16. What does your mom brag about when she talks about you?

  17. Do you feel in alignment with your business?

  18. Do you feel in alignment with your soul?

  19. Do you have any draining clients?

  20. What do you still struggle with?

  21. What does your dream business look like?

  22. Which ones of your products and services inspire you the most?

  23. What was your best customer service experience?

  24. What was your worst customer service experience?

  25. What business inspires you?

  26. How could you be a better leader?

  27. What was the best vacation you ever took?

  28. What is your favorite restaurant?

  29. How would you change the world tomorrow if you could?

  30. What do you want people to remember about you?

  31. What was your biggest achievement?

  32. What tech tools do you use on a daily basis?

  33. What moment would you live over and over?

  34. What would you change from your past?

  35. If you had 36 hours in a day, how would you spend them?

  36. What do you want to see in the world?

  37. If you could trade places with anyone, who would it be?

  38. What do you want your clients and customers to say about you?

  39. What do you never want your clients and customers to say about you?

  40. If you were a fly on the wall with your current client and customers, what would they say about you?

  41. What business contact could change your business?

  42. What business do you wish you could run?

  43. If you had to create a presentation for 10,000 people, what would you say?

  44. What are your main sources for industry news?

  45. If you had to make a million dollars this year, what would you do?

  46. How could you combine your skills and passions to create a new business idea?

  47. Who would you pick for a mentor?

  48. What would you teach a mentee?

  49. What were your favorite classes?

  50. What last made you think, “I wish I had thought of that!”

  51. If you could run 10 businesses, which ones would you run?

  52. How could you celebrate the individuality of your clients?

  53. What was the best dream you ever had?

  54. What would be your worst nightmare?

  55. If you had to make $1,000 in the next five minutes, what could you do?

  56. How could your business change your family’s life?

  57. Who would you meet from history?

  58. What day would you live a hundred times over if you could?

  59. If the next five years went perfectly, what would they look like?

  60. If all of your clients were flying into your town tomorrow, what activities would you plan?

  61. When was the last time you talked to all of your clients?

  62. What makes you feel special?

  63. When did you last feel like you were serving the world?

  64. What makes you nervous?

  65. How will your business stay relevant?

  66. If you had endless energy, what would you do?

  67. How could you cut business expenses and grow business revenue this month?

  68. What do your competitors think of you?

  69. If you had to switch industries, what would you do instead?

  70. What would you like to be better at?

  71. How could you be a better public speaker?

  72. How did you lose your last sale?

  73. How could you gain more sales?

  74. How could you narrow your target market?

  75. If you had to sell your business, how much would you sell it for?

  76. How could you create better content?

  77. How could you package my content to sell?

  78. How could you create not only a live event, but a whole new experience?

  79. What potential do you hide inside?

  80. If you could change bodies, who would you become?

  81. What makes you different?

  82. How will you remain different?

  83. If someone was going to replace you in your business, what would you teach them?

  84. How do you define success?

  85. How did you get to this point?

  86. Are you where you thought you would be?

  87. What is a stupid rule in your industry?

  88. How could you give your employees more independence?

  89. How could you help your clients and customers change their business this month?

  90. If you had to become a professor, what classes would you teach?

  91. If you could make kids all across the world learn one skill, what would it be?

  92. Where do you feel most creative, and are there any environments which lowers your productivity?

  93. What would you tell yourself before you had started your business?

  94. What is your business changing in the world?

  95. How could you change your community?

  96. How could you be happier?

  97. If your business lasts 50 more years, what do you want it to represent?

  98. What do you do when you are discouraged or your ideas are rejected?

  99. What assumption could you test this month?

  100. What day did you make the most money and how?

In the comment section below, please share any questions that have helped you to strengthen connection and customer engagement. Thank You.