AI assistants are surprisingly conservative by default. Push them to be unconventional, and you’ll get dramatically different results. This updated guide shares my favorite techniques for getting fresh, useful responses instead of predictable pablum.
[Editor's note: Are you actually reading these episode notes? If so, I'd love to hear from you. Are they useful? Would you prefer they were shorter summaries of the post, rather than full text? Email jeremy at jeremycaplan.com if you have thoughts or feedback]
The prompts below push ChatGPT, Claude, or whatever other AI tool you prefer to break its conventional patterns, progressing from bland to provocative. The payoff: your AI assistant becomes a creative crane, helping you reach in new directions. Rather than serving as a generic answer machine, your queries can point you toward unexpected angles and radical insights.
5 ways to push AI to be bold
Add weird constraints. Force creative breakthroughs by setting up artificial limitations.
Example: “Help me explain [X] using words a 12-year-old would understand, but make it engaging enough for experts in the field.”
Channel historical problem-solvers. How might figures who made their mark on the past manage my little strategic query.
Example: If Maya Angelou were mediating this team conflict, what questions would she ask that no one else is considering?
Insist on strange cross-pollination. Require the borrowing of concepts, frameworks, or terminology from vastly different domains.
Example: “Analyze my [business / creative project] through the lens of marine biology. What patterns or ecosystem principles could apply here?”
Apply disaster movie logic. Push an AI assistant to consider a workplace problem with the urgency of a crisis scenario to explore unconventional ways to quickly address a slow-moving issue.
Example: “This team project has 48 hours before catastrophic failure. What unconventional resources could we deploy? What rules would we break to succeed?’
Embrace absurd analogies. Challenge the AI to reply in terms that may seem silly at first, but may yield unexpected clarity.
Example: “To help me simplify the most confusing aspect of my presentation, explain my fundraising strategy [X] as if it were a board game instruction manual.”
Give me strange and surprising feedback
When I’m in a creative rut, I paste in a section of writing and prompt AI to be bold and unconventional:
“Offer 5 surprising, bold suggestions for specific ways to improve the following piece of writing. Along with each suggestion, include a detailed, creative explanation with your rationale.”
“Act as an unpredictable, brilliant writing coach who offers strange, quirky, 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. Spotlight what others with radically different perspectives might find problematic if they were to read this with a critical eye. Offer a list of unconventional suggestions for addressing these issues.”
10 odd AI prompts to get radically new results
What are 3 quirky, unusual analogies to explain [your phenomenon of interest]. See my ChatGPT example prompt and result.
Propose 5 questions a reader would be surprised to find answered on [your topic X]. See my ChatGPT example.
Who are 7 surprising, odd historical figures to cite as examples of [X]. For each individual include a detailed explanation. See my Perplexity example.
What rarely discussed, counterintuitive insights on the subject of [X] might startle readers accustomed to bland observations? See my Gemini example.
Give me 5 lively, colorful, unusual words to use in a description of [X]? See my Microsoft Copilot example.
Provide 3 extreme, surprising examples of [X] or silly, ridiculous instances.
Share 5 counterintuitive ways to address situation [X]. See my Grok example
Imagine I shocked people with a one sentence answer to the following question: [X]. Give me 10 versions of that one-sentence reply. See my Jan AI example.
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.
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.
How to get started with provocative prompts
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: Adapt one of the unusual AI prompt templates above to fit your context.
Step 4: Follow-up. After the initial response, iterate. Steer the dialogue in a direction of interest. Ask for even more radical suggestions. AI assistants excel at generating lots and lots of ideas, out of which it’s easier to find one good one.
Step 5. Set up a project (Optional). To create an ongoing space where you get bold, unconventional responses, set up a Claude Project or ChatGPT Project with instructions, and prior examples. Note: both require paid plans. A free alternative: train a bold bot on Poe.
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