1. What are 25 common questions people ask you about your business, product, service, or area of expertise?
  2. If you could wave a magic wand and change one thing for your audience — what would it be and why?
  3. When it comes to your area of expertise, what specific mistakes are you constantly educating people about?
  4. What false beliefs keep people from working with a business like yours?
  5. What three books do you wish every one of your customers would read and why?
  6. What expensive or heartbreaking mistakes do people often make when working with someone like you?
  7. What are signs that someone is getting a good deal, product, or service in your area of expertise?
  8. What are signs that someone is getting a bad deal, product, or service in your area of expertise?
  9. How might someone save money, time, or effort by working with a business like yours?
  10. Write a checklist your audience could use to produce an outcome they really want.
  11. What are the top five hurdles people experience around your topic, product or service area, and what are the best ways to overcome them?
  12. What’s the most common misconception about your industry?
  13. What breaks your heart about what you do?
  14. What lights you up about what you do?
  15. What’s your industry’s biggest controversy right now? Share your opinion.
  16. Who’s your mentor? What lessons did he or she teach you?
  17. What industry terms tend to confuse people, and how can you explain them in a way that’s really easy to understand?
  18. Write a myth vs. fact post about your profession.
  19. What’s the weirdest thing anyone’s said or asked about your business?
  20. Is there anything you thought you could never achieve in your career or business… but you did?
  21. What’s the most important piece of advice you’ve received about your career or business?
  22. What do you tell yourself you “can’t” do? Are you right?
  23. What’s one positive thing someone said to you that changed your mind about something?
  24. What are three major changes you’ve noticed in your industry this year and why is that important for your audience?
  25. What’s the best customer service experience you’ve had and what did you learn?
  26. What questions do you wish your customers would ask you?
  27. What’s your most inspiring customer success story?
  28. How did you get started in your career?
  29. What are your dreams for your career?
  30. Who do you look up to in your industry and why?
  31. What was your first big personal or company failure and what did it teach you?
  32. Which industry experts could you interview that would bring even more insight?
  33. What predictions do you have for where your field or industry is going?
  34. What’s a struggle you’ve overcome?
  35. What’s the biggest mistake you’ve made recently and what did you learn?
  36. What do you wish you knew 10 years ago that you know now?
  37. What’s a struggle you’re having right now that your audience could relate to?
  38. What moment in your life changed everything? [or, fill in the blank. Everything changed when _.]
  39. What time in your life makes you wonder, “What was I thinking?”
  40. What’s the hardest decision you’ve ever made?
  41. Write about a time you faked something.
  42. What’s the best investment you’ve ever made?
  43. What’s the worst investment you’ve ever made?
  44. What’s the most difficult conversation you’ve ever had?
  45. Write about a time when you should’ve said “no” but didn’t.
  46. Write about a time when you should’ve said “yes” but didn’t.
  47. What’s the worst injury you’ve ever had?
  48. What’s the most expensive lesson you’ve ever learned?
  49. Have you ever done something ridiculous to fit in with a group of people?
  50. Finish the sentence: “I’m still embarrassed about _.”
  51. What would you go back and tell your younger self?
  52. Have you ever had a friend who wasn’t good for you?
  53. What strengths do you see in other people that you wish you had?
  54. What are weaknesses you have that you’re always working on?
  55. Share a detailed behind-the-scenes about your typical day.
  56. What are you loving lately? Could be a single recommendation or a themed list.
  57. Are you obsessed with a book, podcast, or quote right now? What about it resonates with you?
  58. Roundup links to your favorite posts on a single topic or during a single week and tell us why we should read them.
  59. Write about the tools you use (in your business or life) every day. What five could you never live without?
  60. What Twitter profiles/blogs/podcasts do you think everyone in your field should follow?
  61. What’s the best purchase under $20 that you made in the last 30 days and why?
  62. What resolution do you make every year?
  63. Which apps could you not live without?
  64. When/where do you get your best ideas?
  65. What five industry-specific books would you recommend to your audience?
  66. What’s your most important habit?
  67. What habit are you working on changing and why?
  68. What’s the most interesting piece of scientific research you’ve read recently?
  69. If you could put anything on a Times Square digital screen, what message would you share and why?
  70. You have three wishes from a genie. What are they?
  71. If you had half the time to do your job, what tasks would you delegate or get rid of completely?
  72. If you could choose one age to be for the rest of your life, what would it be and why?
  73. If someone wanted a career like yours, what would you tell them?
  74. If you could erase one regret from your life, what would it be?
  75. If you had all your financial needs taken care of and never needed to earn another dime, what would you do?
  76. If you could teleport to one place in the world, where would it be?
  77. How would you survive during a zombie apocalypse?
  78. If you knew you had three months to live, how would you spend them?
  79. What’s on your bucket list and why?
  80. What habit would you most love to magically acquire?
  81. If you could pick a superpower, what would it be?
  82. What natural talent do you most wish you had?
  83. What movie can you recite by heart every time it’s on TV?
  84. Do you remember a commercial from your childhood? What was it for, and why did it stick with you?
  85. How many times in your life have you moved? What did you learn from it?
  86. What’s your earliest memory around money?
  87. Can you remember the first dream you had?
  88. Who was your childhood best friend? Are they still in your life?
  89. What teacher do you remember the most, and why?
  90. Do you have any superstitions?
  91. Who or what was your first love and why?
  92. What’s your favorite meal and why?
  93. What family photo do you remember best? Describe it and what it makes you think about.
  94. Do you have a favorite day of the week? Why?
  95. Do you consider yourself “lucky”? Why or why not?
  96. Do you have a great, totally useless skill?
  97. What did you want to be when you grew up?
  98. If you could invent anything, what would it be?
  99. Tell us what’s on your bedside table right now.
  100. What’s the wildest story you always tell at parties?
  101. What makes you happy every time you see it?