100 interview questions to draw your book out of you

The follow-up questions (use these most)

A first answer is usually the version you have told a hundred times: tidy, general and a little flat. The material a reader remembers comes out on the second and third pass. Whoever is asking should keep these ten follow-ups in front of them and use one after almost every answer:

1. Give me an example.
2. What happened next?
3. What did you actually say? What did they say back?
4. Where were you? Who else was there?
5. How did you feel at that moment?
6. What did it cost? In money, time or something else?
7. What would most people have done instead?
8. Why does that matter to the reader?
9. Say that again, but as if I were twelve.
10. Is there a story that proves it?

Origin story (questions 1 to 12)

These belong in the introduction or first chapter. They explain why the reader should trust you, so look for moments, not a resume.

1. When did you first notice the problem this book is about?
2. What were you doing for work at the time?
3. Who taught you the most about this subject, and what did they teach you?
4. What is the first time you got it badly wrong?
5. What made you decide to do something about it?
6. What did people around you think when you started?
7. What did you believe then that you no longer believe?
8. When did you realize you had a method and not just a habit?
9. What is the moment you would open a documentary about your work with?
10. Why are you writing this book now, and not five years ago?
11. Who do you picture reading it?
12. What do you want that person to do the day they finish it?

The problem (questions 13 to 24)

Readers buy a nonfiction book to solve a problem. These questions make the problem vivid enough that the reader sees themselves in it.

13. In one sentence, what problem does your reader have?
14. How does the problem show up on an ordinary Tuesday?
15. What does the reader tell themselves about why it is happening?
16. What is the real cause, in your view?
17. What does the problem cost people who leave it alone?
18. What have your readers already tried that did not work?
19. Why did those things not work?
20. Who gets hurt by this problem besides the reader?
21. What is the most common misunderstanding about it in your field?
22. What does the reader's life look like when the problem is solved?
23. How do people know they have this problem before they can name it?
24. Tell me about the client who had the worst case of it you have seen.

The method (questions 25 to 36)

This is the spine of most business and expertise books. Get the whole method on tape in one session before you go step by step.

25. Walk me through your method from start to finish, as if I were a new client.
26. How many steps or parts does it have, and what is each called?
27. Why are they in that order?
28. Which step do people want to skip? What happens when they do?
29. Where did each part of the method come from?
30. What is the one idea underneath all of it?
31. How is your approach different from the standard advice?
32. Who is the method not for?
33. What does a person need before they can start?
34. How long does it take to see results, honestly?
35. How do you know it is working?
36. If the reader only remembers one thing, what should it be?

Each step (questions 37 to 50)

Run this group once for every step of your method, usually one step per session. Each pass gives you the raw material for one chapter.

37. What is this step, in plain words?
38. Why does it matter?
39. What does it look like when someone does it well?
40. What does it look like when they do it badly?
41. What exactly should the reader do first?
42. What tools, templates or questions do you use for this step?
43. How long should it take?
44. What are the warning signs that it is going wrong?
45. Tell me about a client who struggled with this step.
46. Tell me about a client who got it right.
47. What do you do in this step that you have never written down?
48. What would you check if you were reviewing someone's work on it?
49. How does this step set up the next one?
50. What is the exercise you would give the reader to try this week?

Objections (questions 51 to 62)

Every reader arrives with doubts. Answering them in the book, in your voice, is what makes the reader keep going.

51. What is the first objection people raise when you explain this?
52. What do skeptics in your field say about your approach?
53. Where are they right?
54. "I do not have time for this." What do you say?
55. "This will not work in my industry." What do you say?
56. "We tried something like this and it failed." What do you say?
57. "It costs too much." What do you say?
58. What is the honest downside of your method?
59. When would you tell someone not to follow your advice?
60. What evidence would change your mind?
61. What question do clients ask that they are embarrassed to ask?
62. What do people secretly fear about making this change?

Client stories (questions 63 to 76)

Stories carry a nonfiction book. Before you record any client story, decide whether you will change names and details, and ask permission where you need it.

63. Which client story do you tell most often? Tell it now, slowly.
64. Where were they when they first came to you?
65. What had they already tried?
66. What was the first conversation like?
67. What did you notice that they had not?
68. What was the turning point?
69. What resistance did they put up?
70. What changed, and how do you know?
71. What did they say to you afterward?
72. Which client did not succeed, and why?
73. Which client surprised you?
74. Which client taught you something that changed your method?
75. Is there a client whose story would make the reader say "that is me"?
76. Which story would you only tell with names changed?

Mistakes (questions 77 to 88)

Readers trust authors who admit what went wrong. These answers often become the most read pages of the book.

77. What is the biggest mistake you made in your own work on this?
78. What did it cost you?
79. When did you realize it was a mistake?
80. What did you do to fix it?
81. What mistake do you see beginners make most?
82. What mistake do experienced people make that beginners do not?
83. What advice did you follow early on that turned out to be wrong?
84. What do you wish someone had told you ten years ago?
85. Which of your own rules have you broken, and what happened?
86. What mistake are you still trying to stop making?
87. What looked like a mistake at the time but turned out right?
88. How should the reader recover if they make the same mistake?

The future (questions 89 to 100)

These shape the final chapter and the conclusion, which is where readers decide whether to act.

89. What is changing in your field over the next five years?
90. What will stay the same no matter what changes?
91. What will happen to people who ignore this book's advice?
92. What becomes possible for people who follow it?
93. What do you hope your industry looks like in ten years?
94. What part of the problem is still unsolved?
95. What are you working on next?
96. What should the reader do in the first week after finishing the book?
97. What should they do in the first year?
98. Where should they go to learn more?
99. If you could ask every reader to do one thing, what would it be?
100. What do you want to be remembered for?

How to run a session with this list

1. Choose the chapter

   One chapter per session. Write the chapter's one point at the top of the page so both of you remember why you are there.

2. Pick 10 to 15 questions

   Usually from one or two groups. For a step chapter, use the "each step" group plus two or three client story and mistake questions.

3. Warm up with an easy story

   Start with a question you can answer without thinking. The first few minutes are rarely the best; you are getting used to the microphone.

4. Follow the energy

   When an answer gets specific or emotional, stay there with follow-ups. Go back to the list only when the thread runs out.

5. Close with gaps

   In the last five minutes, ask: "What did we not cover that belongs in this chapter?" Note the answer as the start of the next session.

If you are interviewing yourself, read each question aloud before answering. It sounds odd, but hearing the question puts you in answering mode rather than writing mode. If someone else is interviewing you, send them the chapter's questions a day ahead; the guide to being interviewed has a briefing template. Professional book interviewers, such as the writers at Scribe Media, work from their own versions of lists like this one and spend most of the session on follow-ups.