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Here are some surprising (and fun) ways to prompt AI

Originally posted on fastcompany.

To avoid predictable responses, try instructing AI engines to be get weird.

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AI outputs can be disappointingly conventional. To avoid predictable responses, I like instructing AI engines to be strange. Unexpected, radical ideas can be useful for creative inspiration. Odd perspectives stretch my thinking. Read on for specific ways to prompt AI to break beyond its bland boundaries.


When I’m in a creative rut, I paste in a section of writing and prompt AI to be bold and unconventional:

  • “Offer five surprising, unexpected suggestions for specific ways to improve the following piece of writing. Along with each suggestion, include a detailed, creative explanation with the rationale for the observation.”
  • “Act as an unpredictable, brilliant writing coach who offers strange, bold, creative suggestions. Provide specific, granular input.”
  • “Detail novel topic ideas or peculiarly provocative questions I could answer to help me disrupt the conventionality or predictability of the following outline I’ve begun.”
  • “Point out blindspots that others with radically different perspectives from mine on this subject might identify if they were to read this work with a critical eye. Include examples of ways in which these could be remedied.”


To create distinctive illustrations I rely on DALL-E 3, an image generator included with my $20 monthly ChatGPT plus subscription. It understands natural language, so I don’t have to master prompting lingo to get results that surprise me.

  • Tip: Prompt for wide images. Those tend to look better than square images when laid out in newsletters, blog posts and other wide-format pages.

And here are some good free alternatives for creative imagery:

  • Microsoft’s Designer lets you generate distinctive images for free, with the same DALL-E 3 engine a ChatGPT subscription offers. You get four images to choose from each time you write a prompt, increasing the likelihood at least one will suit you.
  • Adobe Firefly is also useful for envisioning wild images. You can alternatively use it to edit existing images. You can select part of an image you want to change and explain what you’d like instead.


  1. Propose 5 questions a reader would be surprised to find answered on [your topic X]
  2. What are 3 quirky, unusual analogies to explain [your phenomenon of interest]. Here’s an example prompt and result.
  3. Who are 7 surprising, odd historical figures to cite as examples of [X]. For each individual include a detailed explanation. Here’s an example.
  4. What rarely discussed, counterintuitive insights on the subject of [X] might startle readers accustomed to bland observations?
  5. Give me 5 lively, colorful, unusual words to use in a description of [X]?
  6. Provide 3 extreme, surprising examples of [X] or silly, ridiculous instances.
  7. Share 5 counterintuitive ways to address situation [X]
  8. Imagine I shocked people with a one sentence answer to the following question: [X]. Give me 10 versions of that one-sentence reply.
  9. I have [X challenge] in [Y situation]. Assume I want to surprise people with a wildly creative solution. Describe three solutions that would stun people while addressing the root of the issue.
  10. For a syllabus I’m creating on [X], imagine seven radically different people teaching the same course. Provide three bullet points representing each teacher, explaining the surprising and distinct learning outcomes each would aim for in their version of the class.


  • Step 1: Pick an AI chat tool to experiment with: ChatGPT, Claude, Gemini or Microsoft Copilot.
  • Step 2: Initiate a new chat by typing in a role for the AI to adopt for the prompt you’re going to give it. For example: “Act as a bold, experienced, expert who provides distinctive, unusual perspectives to push my thinking in creative new directions.”
  • Step 3: Pick one of the unusual AI prompt templates above and adapt it to fit the specifics of your own work.
  • Step 4: After you get an initial response, write a follow-up prompt to build on the first result. That iteration allows you to tailor subsequent answers. Consider asking for even more radical suggestions, or for more depth on a particular detail.

Source: fastcompany

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