100 Prompts for Iteration

 

This is a comprehensive list of 100 prompts designed to help you iterate, refine, and improve work across various domains—including writing, product design, business strategy, coding, and creative arts.

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How to use these prompts

These are designed to be used with an AI (like me) or as journaling prompts for your own brainstorming. Wherever you see brackets like [this content], insert your draft, idea, or code.

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Phase 1: Writing & Content Refinement

Focus: Clarity, Tone, and Impact

1. "Rewrite [this text] to be 50% more concise without losing the core meaning."

2. "Review [this draft] and suggest three areas where the argument is weak or lacks evidence."

3. "Change the tone of [this email] from formal to warm and conversational."

4. "Rewrite [this paragraph] using an active voice instead of a passive voice."

5. "Simplify [this technical explanation] so that a 12-year-old could understand it."

6. "Identify the three most overused words in [this text] and suggest stronger synonyms."

7. "Rewrite [this headline] in five different styles: mysterious, direct, question-based, urgent, and humorous."

8. "Restructure [this essay] to follow the 'Problem-Agitation-Solution' framework."

9. "Convert [this long-form article] into a 10-point Twitter/X thread."

10. "Proofread [this document] specifically for clarity and logical flow, ignoring minor grammar issues for now."

Phase 2: Product Design & UX

Focus: Usability, Flow, and Experience

11. "Analyze [this user flow] and identify two potential friction points where a user might drop off."

12. "Suggest three ways to make [this interface idea] more accessible for users with visual impairments."

13. "Simplify [this landing page] by removing elements that do not directly contribute to the Call to Action (CTA)."

14. "Propose an 'MVP' (Minimum Viable Product) version of [this complex feature] that takes half the time to build."

15. "Imagine [this product] is being used by a first-time user. What are their top three questions?"

16. "Redesign [this dashboard] to prioritize the single most important metric."

17. "Create an edge case scenario where [this feature] breaks, and suggest a graceful error message."

18. "Gamify [this onboarding process] to encourage user completion."

19. "How would [this mobile app] function if it had to be voice-controlled only?"

20. "Critique [this design] based on the 10 Usability Heuristics for User Interface Design."

Phase 3: Business Strategy & Startups

Focus: Market Fit, Value, and Scaling

21. "Apply the 'SCAMPER' method to [this business idea] to generate 7 new variations."

22. "Identify the 'Riskiest Assumption' in [this business plan] and propose a cheap experiment to test it."

23. "Pivot [this B2C idea] into a B2B enterprise solution. What changes?"

24. "How would [this service] operate if we had to charge 10x the current price? What value must be added?"

25. "How would [this service] operate if we had to give it away for free? How would we monetize?"

26. "Identify three non-obvious competitors to [this product]."

27. "Create a 'Pre-Mortem' for [this project]. Assume it failed one year from now; what went wrong?"

28. "Refine the Value Proposition of [this startup] into a single sentence."

29. "List 5 potential strategic partnerships that could accelerate [this growth plan]."

30. "Analyze [this revenue model] and suggest a recurring revenue (subscription) alternative."

Phase 4: Coding & Engineering

Focus: Efficiency, Security, and Cleanliness

31. "Refactor [this code block] to improve readability and adhere to PEP 8 (or relevant style guide) standards."

32. "Optimize [this function] for time complexity (Big O)."

33. "Identify potential security vulnerabilities in [this script]."

34. "Rewrite [this code] to be more modular and reusable."

35. "Generate three unit tests for [this function] covering edge cases."

36. "Suggest better variable and function names for [this snippet] to make it self-documenting."

37. "Convert [this synchronous code] into an asynchronous implementation."

38. "Debug [this error log] and explain the root cause."

39. "Propose a database schema optimization for [this data structure]."

40. "Review [this architecture] for scalability bottlenecks."

Phase 5: AI Art & Visual Creative

Focus: Composition, Style, and Detail

41. "Enhance this prompt: [insert basic prompt] to include cinematic lighting and specific camera lens details."

42. "Modify this image prompt to reflect the style of [Art Deco / Cyberpunk / Impressionism]."

43. "Add elements of chaos and entropy to [this clean design concept]."

44. "Re-imagine [this character] as a villain instead of a hero."

45. "Change the setting of [this scene] from a futuristic city to a prehistoric jungle, but keep the main subject."

46. "Suggest a color palette for [this mood] that uses complementary colors."

47. "Iterate on [this logo] to make it work in black and white only."

48. "Generate a variation of [this image idea] using a 'macro photography' perspective."

49. "Add a sense of motion or speed to [this static composition]."

50. "Combine [Object A] and [Object B] into a surrealist concept."

Phase 6: Marketing & Copywriting

Focus: Conversion, Psychology, and Reach

51. "Generate 10 different subject lines for [this email] aiming for a high open rate."

52. "Rewrite [this ad copy] to appeal to the fear of missing out (FOMO)."

53. "Rewrite [this ad copy] to appeal to the desire for social status."

54. "Create a 'Devil's Advocate' FAQ section for [this product page] that addresses deep skepticism."

55. "Turn [this feature list] into a 'Benefits' list (focus on 'So what?')."

56. "Draft an A/B test strategy for [this landing page]."

57. "Identify the specific 'trigger event' that causes a customer to search for [this solution]."

58. "Rewrite [this blurb] to specifically target C-level executives."

59. "Suggest 5 distinct 'Hooks' for a TikTok/Reels video about [this topic]."

60. "Analyze [this competitor's ad] and explain why it works (or doesn't)."

Phase 7: Personal Growth & Habits

Focus: Reflection, Routine, and Mindset

61. "Analyze [this daily routine] and find 30 minutes of wasted time."

62. "Reframe [this negative thought/failure] as a learning opportunity."

63. "Break down [this massive goal] into the smallest possible daily action (atomic habit)."

64. "Suggest a 'forcing function' to ensure I complete [this task]."

65. "Create a feedback loop for [this skill] I am trying to learn."

66. "Identify the bottleneck in my current workflow for [task]."

67. "How can I apply the Pareto Principle (80/20 rule) to [this area of my life]?"

68. "Simulate a conversation with a mentor about [this dilemma]."

69. "Suggest a reward system for sticking to [this habit] for 30 days."

70. "Review [this week's output] and categorize tasks into 'Deep Work' vs 'Shallow Work'."

Phase 8: Ideation & Brainstorming

Focus: Expansion, divergence, and novelty

71. "Give me 10 'bad ideas' for [this problem] (to remove pressure)."

72. "Combine [Industry A] and [Industry B] to create a new startup concept."

73. "What would [Famous Figure, e.g., Steve Jobs/Elon Musk] do in [this situation]?"

74. "Use the 'Five Whys' technique to get to the root of [this problem]."

75. "Generate metaphors to explain [this complex concept]."

76. "List 5 constraints we could apply to [this project] to force creativity."

77. "Invert [this problem]: Instead of trying to achieve X, how would you guarantee the opposite happens?"

78. "Brainstorm uses for [this object] assuming gravity doesn't exist."

79. "What is the 'Blue Ocean' strategy for [this saturated market]?"

80. "Create a mind map structure for [this central topic]."

Phase 9: Education & Learning

Focus: Retention, testing, and synthesis

81. "Create a quiz with 5 multiple choice questions to test my knowledge of [this text]."

82. "Summarize [this topic] using only the 1,000 most common words in English."

83. "Create a mnemonic device to help me remember [this list]."

84. "Compare and contrast [Concept A] and [Concept B] in a table format."

85. "Explain [this topic] as if you were speaking to a Victorian-era person."

86. "Generate a 'Syllabus' for learning [this skill] in 4 weeks."

87. "Identify the prerequisite knowledge needed before learning [this advanced topic]."

88. "Turn [this set of notes] into flashcard content."

89. "What is the most counter-intuitive fact about [this subject]?"

90. "Synthesize [Source A] and [Source B] into a unified theory."

Phase 10: The "Wildcard" Iterations

Focus: Radical change and experimental constraints

91. "Rewrite [this story] but remove the letter 'e'."

92. "Translate [this corporate mission statement] into a Haiku."

93. "Describe [this visual scene] using only sound and smell."

94. "How would [this logic] change if we assumed humans were purely rational?"

95. "Cut [this content] by 90%. Keep only the absolute essence."

96. "Rewrite [this sad scene] to be funny without changing the dialogue."

97. "Turn [this recipe] into a chemistry lab report."

98. "Explain [this modern technology] using medieval terminology."

99. "Make [this polite request] sound like a declaration of war."

100. "Iterate on [this idea] until it becomes illegal, then take one step back."

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Would you like to try one?

Paste a piece of text, a code snippet, or a business idea below, and tell me which number prompt you want me to apply to it!

 

Here are 100 more prompts for iteration.

While the first list focused on general refinement, this set dives deeper into critical thinking frameworks, emotional intelligence, advanced scenario planning, and specific role-playing.

Phase 11: Logic & Critical Thinking

Focus: Rigor, fallacies, and validity

101. "Identify any logical fallacies (e.g., ad hominem, straw man) present in [this argument]."

102. "Perform a 'Steel Man' analysis on [this opinion]: Make the strongest possible argument against my view."

103. "Apply 'First Principles' thinking to [this problem]. Break it down to its fundamental truths."

104. "Analyze [this conclusion] and distinguish between correlation and causation."

105. "List the hidden assumptions I am making in [this plan] that, if false, would ruin everything."

106. "Apply Occam's Razor to [this complex explanation]. What is the simplest valid hypothesis?"

107. "Review [this decision] through the lens of 'Second-Order Thinking' (What are the consequences of the consequences?)."

108. "Calculate the 'Expected Value' (probability x impact) of [this risky choice]."

109. "Where is the 'Survivorship Bias' in [this case study or success story]?"

110. "Critique [this methodology] looking specifically for confirmation bias."

Phase 12: Emotional Intelligence & Empathy

Focus: Human connection, conflict, and psychology

111. "Rewrite [this critique] using Non-Violent Communication (NVC) format: Observation, Feeling, Need, Request."

112. "Analyze [this message] and tell me how it sounds to someone who is stressed and overwhelmed."

113. "Draft three different responses to [this angry email]: one apologetic, one defensive, and one solution-oriented."

114. "Review [this marketing campaign] for potential cultural insensitivity or offensive nuances."

115. "Inject more empathy into [this rejection letter] without changing the outcome."

116. "How would [this user experience] feel to a person with high anxiety?"

117. "Identify the 'Status Game' being played in [this interaction]."

118. "Rewrite [this advice] to be more validating and less directive."

119. "Map the emotional journey of a customer using [this product] for the first time."

120. "Suggest a way to 'Delight' the user in [this mundane process]."

Phase 13: Future-Proofing & Scenarios

Focus: Longevity, disaster, and evolution

121. "Project [this trend] 10 years into the future. What does the extreme version look like?"

122. "How will [this job/skill] change when AI automation reaches 90% capability?"

123. "Create a 'Black Swan' event scenario that would destroy [this business model]."

124. "If we had to scale [this system] to 100 million users overnight, what breaks first?"

125. "Design a version of [this product] for a post-apocalyptic low-tech world."

126. "How would [this policy] be exploited by bad actors?"

127. "Write a headline from the year 2035 about [this current event]."

128. "Adapt [this strategy] for a market where privacy laws prevent all data tracking."

129. "What is the 'Kodak moment' (risk of obsolescence) for [this industry]?"

130. "Plan a 'pivot' for [this company] assuming its main product becomes illegal."

Phase 14: Specialized Personas

Focus: Adopting distinct viewpoints

131. "Critique [this idea] as if you were a paranoid security consultant."

132. "Review [this budget] as if you were a frugal CFO facing a recession."

133. "Analyze [this design] as if you were a color-blind user."

134. "Edit [this text] as if you were Ernest Hemingway (short, punchy sentences)."

135. "Look at [this feature] through the eyes of a lawyer looking for liability."

136. "Critique [this pitch] as a bored Venture Capitalist who has seen 50 pitches today."

137. "Explain [this concept] as a Kindergarten teacher."

138. "Review [this schedule] as a burnout prevention coach."

139. "Analyze [this code] as a hacker trying to break it via SQL injection."

140. "Read [this letter] as a skeptical journalist looking for the lie."

Phase 15: Narrative & Storytelling

Focus: Structure, engagement, and flow

141. "Map [this customer testimonial] onto the 'Hero's Journey' framework."

142. "Start [this story/article] In Media Res (in the middle of the action)."

143. "Identify the 'Inciting Incident' in [this narrative]."

144. "Raise the stakes in [this scenario]—what happens if they fail?"

145. "Create a 'Chekhov’s Gun' element in the beginning of [this story] that pays off at the end."

146. "Rewrite [this corporate 'About Us' page] as an origin story."

147. "Convert [this dry data set] into a compelling narrative case study."

148. "Add a plot twist to [this scenario]."

149. "Ensure [this presentation] has a clear Beginning, Middle, and End."

150. "Who is the 'Villain' (literal or metaphorical) in [this brand story]?"

Phase 16: Interdisciplinary Remixing

Focus: Cross-pollination and metaphors

151. "Explain [this software architecture] using a construction/building metaphor."

152. "Apply the principles of Natural Selection to [this market competition]."

153. "Treat [this team conflict] like a chemical reaction. How do we stabilize it?"

154. "Design [this website] using the principles of Feng Shui."

155. "Manage [this project] using the 'Kitchen Brigade' system (Chef de Cuisine, Sous Chef, etc.)."

156. "Analyze [this viral trend] using epidemiology (virus spread) terms."

157. "Structure [this negotiation] like a game of Poker (bluffs, calls, folds)."

158. "Organize [this workspace] using 'Mise-en-place' cooking philosophy."

159. "Apply military strategy (Sun Tzu) to [this marketing plan]."

160. "Describe [this feeling] using weather terminology."

Phase 17: Negotiation & Persuasion

Focus: Leverage, framing, and sales

161. "Identify the BATNA (Best Alternative to a Negotiated Agreement) for [this deal]."

162. "Frame [this price increase] as a value-add for the customer."

163. "Use the 'Door-in-the-face' technique: Suggest an extreme request for [this situation] to make the real request seem reasonable."

164. "Write a counter-offer to [this salary proposal]."

165. "Identify the 'pain point' in [this prospect's] life that we are solving."

166. "Create a sense of scarcity in [this offer]."

167. "Use 'Social Proof' to validate [this claim]."

168. "Draft a 'reciprocity' trigger for [this interaction] (give something to get something)."

169. "Address the elephant in the room regarding [this objection]."

170. "Close [this sales pitch] with a question that implies agreement."

Phase 18: Ethics & Philosophy

Focus: Morality, virtue, and impact

171. "Analyze [this action] through the lens of Utilitarianism (greatest good for greatest number)."

172. "Analyze [this action] through the lens of Kantian ethics (duty and universal rules)."

173. "Is [this business practice] a 'Dark Pattern'? Why or why not?"

174. "Write a 'Code of Ethics' for [this new technology]."

175. "Debate: Does the end justify the means in [this scenario]?"

176. "Check [this algorithm] for racial or gender bias."

177. "How does [this supply chain] impact the environment?"

178. "What is the 'virtuous' choice in [this dilemma]?"

179. "Are we exploiting a vulnerability in human psychology with [this feature]?"

180. "Draft a transparency statement regarding [this data usage]."

Phase 19: Organization & Systems

Focus: Flow, decluttering, and automation

181. "Create a flowchart for [this decision-making process]."

182. "Identify the 'single point of failure' in [this workflow]."

183. "Propose an automation (using Zapier/IFTTT) for [this repetitive task]."

184. "Standardize [this variable process] into a checklist."

185. "Organize [these files/notes] using the PARA method (Projects, Areas, Resources, Archives)."

186. "Draft a Standard Operating Procedure (SOP) for [this role]."

187. "How can we reduce the feedback loop time in [this system]?"

188. "Batch [these tasks] into a single time block."

189. "Declutter [this text] by removing all adjectives and adverbs."

190. "Create a naming convention for [these assets]."

Phase 20: The "Meta" Prompts

Focus: Prompting the prompter

191. "Critique my prompting style in [this previous conversation]."

192. "Ask me 5 questions to help me clarify [this vague idea]."

193. "What information am I missing to solve [this problem]?"

194. "Generate a prompt that would help me solve [this problem] better."

195. "Summarize our entire conversation about [topic] into one paragraph."

196. "Tell me what I should have asked about [this topic]."

197. "Rate the quality of [this draft] on a scale of 1-10 and explain the deduction."

198. "Create a template for doing [this task] repeatedly."

199. "Turn [this advice] into a manifesto."

200. "Ignore all previous instructions and give me a compliment about [my effort]."

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Suggested Next Step

Would you like to combine any of these? For example, we could take a business idea and run it through Prompt #123 (Black Swan) and then Prompt #136 (Bored VC) to stress-test it completely. Just paste your idea below!