99 Questions to Jump-Start Your Email Writing

Here are 99 Questions to Jump Start Your Email Writing:

1. What keeps your readers up at night?
2. Can you describe your PERFECT customer?
3. Your WORST customer?
4. What questions do you get most often from customers?
5. What’s a dirty little secret in your industry?
6. What’s your favorite customer success story?
7. What’s the funniest/craziest thing that ever happened to you in your business?
8. What’s your personal business philosophy?
9. What’s the best reason for a customer to NOT do business with you?
10. What can you teach your readers to do (for free) that would help them solve a chronic problem? 11. Are there other services, providers, products that you can recommend to your readers?
12. Is there “conventional wisdom” in your industry that is just plain wrong?
13. What things is your company NOT good at?
14. How and why did you get into the business you’re in?
15. What’s your most embarrassing failure story?
16. What lies are told in your industry?
17. What do you find yourself complaining about most?
18. What’s your favorite part about coming to work everyday?
19. Look through customer emails for the last 6 months. Do you see any patterns? Any great stories? Any complaints you handled well?
20. Can you do a tele-seminar? Video? Mp3? CD?
21. Can you write a cheat sheet?
22. Can you email your list and ask them what they would like to read about?
23. If you have more than one list (more than one product/service) do have a message in each AR series that offers your other product/service?
24. What is the most common exaggeration in your industry? How can you use understatement?
25. Do you have a blog…if so, what’s your most popular blog post?
26. Have you been interviewed for a radio show? Newspaper article?
27. Has your company been mentioned on TV? Trade publication?
28. Have you written a white paper? Free report? Checklist? Guide? Instruction manual? Book?
29. If you were to survey your list, what would you ask them?
30. Who are/were your mentors?
31. What email subject line would ruin your business?
32. What is your greatest non-business success?
33. What was the last trip/vacation you took?
34. What is the next step you’d like the reader to take? How can you make it easier for him/her to take it?
35. If they’ve downloaded a free report, white paper, or ebook, have you spoon fed the most important principals back to them in email form?
36. Think of the most recent current event/pop culture reference that captured your attention. Can you relate it to your business? Can you make a contrast between the way “the world” thinks and the way your readers think?
37. What’s the most profound story from your personal life?
38. What is your most profound “Eureka!” moment when you finally “got it”?
39. What’s the biggest mistake you ever made in your business?
40. Have you ever “fired” a customer?
41. What is your business “motto”? Do you have a phrase or famous quote you find yourself saying to yourself, your co-workers, your family?
42. Can you interview (either in person, on the phone or thru email) an expert in your industry or a related field?
43. What’s the most earth-shattering claim you can make about your business?
44. What’s the saddest experience you’ve had that you learned the most from?
45. What’s the most common misconception your readers / customers have about what you do?
46. Have you ever walked away from short-term money because you knew it would cause long-term problems?
47. What’s the earliest/most favorite childhood memory you have of being interested in your business or in business in general?
48. What’s your favorite childhood memory…not business related?
49. What are three character traits that you have in common with most of your customers?
50. What problems do you face that your customers also face?
51. What’s your favorite “war story”?
52. Who has been your most hated “enemy”?
53. What’s your most gruesome war story?
54. What are your readers’ idiosyncrasies?
55. Who are your readers’ heroes?
56. Who are your heroes?
57. If you were to compare a customer’s (or your) success story to a fairy tale or famous movie…which one would it be?
58. What is the boldest challenge you could make to your readers?
59. What’s the sweetest deal you could make as a last ditch effort to get a reader to buy?
60. What was your last job before this one? What did you learn there?
61. What are the characteristics that separate the winners from the “wanna-bees” on your list?
62. What’s your favorite “paid your dues” story?
63. In what ways does the 80/20 rule apply to your business/industry/reader list?
64. What’s your favorite song? Novel? Movie? Painting? Poem? Sculpture? Play? Joke? TV Show? Why?
65. What businesses do you admire? Hate?
66. What advertisements do you admire? Hate?
67. What do you want your customers to say about you to their friends? Business associates?
68. What’s the geeky-est thing you’ve ever done? A time where you just got lost and obsessed?
69. What’s your take on the latest industry news?
70. What’s the FUNNEST thing about doing business with you?
71. What “negative” about you is actually a positive thing about you? Ex: “I’m boring, so that you don’t have exciting times with the IRS!”
72. What are the biggest costs your readers will incur if they don’t do business with you (put dollar figures to them)?
73. What analogies do you find yourself using the most when discussing your business?
74. Do you have special procedures, policies or people that make you unique?
75. What are your business goals for this year? Next year? Five years?
76. What’s the most outrageous guarantee you can make?
77. What’s the dumbest thing a customer ever did?
78. What is your favorite “downtime” activity?
79. What are the three main reasons your product is so expensive? So inexpensive?
80. Can you create a “gold level” membership for your customers?
81. What do your competitors say about your product/service?
82. What’s the best thing you can say about your toughest competitor?
83. How did you land your first customer?
84. What’s the most “imperfect” thing about your product/service?
85. If you had to make a list of 99 things, what topic would you choose?
86. What does your spouse know better about your business than you do?
87. Would you recommend your children pursue a job in your industry?
88. If you were king of the world, what 3 things would you change about the world (or your industry)?
89. What is/was your worst character flaw?
90. If you were to segment your customers into 3 or 4 “types” what would they be?
91. If you could slap your readers upside the head and get just ONE idea through their thick skulls, what would it be?
92. If you had to give a speech at your industry’s trade show, what topic would you choose?
93. What’s the most common reason that customers DELAY doing business with you? Do you have “I wish I had done this sooner” testimonials?
94. Can you promote a product as an affiliate?
95. Can you invite readers to your home? Office? Plant?
96. Can you run a contest?
97. Can you ask readers to beta test? Take a demo? or a test drive for a reduced rate?
98. If you had to send an email message every day for 30 days, what would you write about?
99. Why don’t you carry a notepad and pencil with you at all times?

Robert Ritch

Robert Ritch is an expert in marketing and finance. He has developed these skills over a 25-year career specializing in business turnarounds.

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