We’ve been spelunking deep into the AI prompt rabbit hole so you don’t have to.
Each month, our team curates the most clever, creative, and productivity-boosting AI prompt tips from around the internet—and puts them to the test. This is your monthly cheat sheet, a behind-the-scenes pass to the strategies that actually work (and the ones that hilariously don’t).
This isn’t some fluffy listicle. These are prompt experiments we’ve run, refined, and sometimes regretted. From getting ChatGPT to rewrite your resume like a Fortune 500 recruiter to convincing Gemini to finally give a straight answer, May’s tips are packed with real wins.
🧠 Check out the April 2025 Prompt Tips of the Day →
Pro tip: Don’t just scroll. Bookmark this. Some of these might sound odd (looking at you, historical therapy prompts), but they just might change how you use AI forever.
Grab a coffee, crack your knuckles, and get ready to upgrade your AI skills. May’s tips are here—and they’re sharp.
May 1, 2025
Want to turn your AI writing assistant into a ruthless editor that actually improves your work? We've discovered a meta-prompt hack that transforms ChatGPT into your personal writing roast master and instant rewrite wizard.
Here's the workflow: First, ask the AI to list the top 5 weaknesses in your draft. Then, have it rewrite the piece addressing every single flaw. It's like having a snarky editor who moonlights as a ghostwriter—minus the coffee breath and passive-aggressive sticky notes.
The prompt:
I want you to help me improve this draft. Here's my process:
STEP 1: Critically analyze my draft. List the top 5 specific weaknesses in the writing, including:
- Structural issues
- Clarity problems
- Tone inconsistencies
- Grammatical or stylistic weaknesses
- Logical gaps or unsupported arguments
For each weakness, provide:
- A clear explanation of the problem
- Why it matters
- A specific suggestion for improvement
STEP 2: After listing the weaknesses, completely rewrite the draft. Your new version should:
- Address every weakness you identified
- Maintain the core message of the original draft
- Improve overall readability and impact
- Use a tone similar to the original draft
STEP 3: Create a side-by-side comparison showing:
- Original draft weakness
- Your proposed fix
- Reasoning behind the change
Be ruthlessly honest but constructive. My goal is to improve my writing, not to feel discouraged.
[INSERT DRAFT HERE]
–
Our favorite insight? This approach isn't just about criticism. It's a stealth learning mechanism that helps you understand your writing blind spots. Each roast is a mini-masterclass in improvement.
Pro tip: The key is in the prompt. Ask for specific, constructive feedback, not just vague criticism. Think "surgical strike" over "carpet bombing" when it comes to editing.
May 2
The Assumption Hunter hack turns ChatGPT into your reality-check wingman. I dumped my “foolproof” product launch into it yesterday, and within seconds it flagged my magical thinking about market readiness and competitor response—both high-risk assumptions I was treating as facts.
Paste this prompt:
“Analyze this plan: [paste plan] List every assumption the plan relies on. For each assumption:
- Rate its risk (low / medium / high)
- Suggest a specific way to validate or mitigate it.”
This’ll catch those sneaky “of course it'll work” beliefs before they catch you with your projections down. Way better than waiting for your boss to ask “but what if...?”
May 5
Try this out: When writing something complicated with AI, ask it: “Would my mom (or dad) understand this?”
We literally pulled this from our own style guide and now use it as an actual prompt with ChatGPT and Claude. The results are night-and-day clearer.
Instead of asking for a simple explanation, try: “Explain [whatever] so my mom would understand it.” The AI immediately drops the technical posturing and delivers surprisingly useful explanations.
Don’t forget: Get specific about your mom! “Explain this to my mom who's a gardener but has never used ChatGPT” works 10x better than generic “explain simply.”
Copy this prompt:
“Explain [topic] using the 'Would my mom understand this?' test. Make it conversational, jargon-free, and include a real-world analogy she'd relate to.”
May 6
The “Spec Sheet Squeeze” technique transforms generic AI responses into tailored gold. Instead of asking for “a marketing plan,” ask for “a marketing plan with these exact specifications” followed by a bulleted list of your requirements. We tested this on Claude and ChatGPT this week—the difference was night and day.
Just structure your prompt like this: “Create [deliverable] that includes: • [specific element 1] • [specific element 2] • [formatting requirements]”
The more detailed your spec sheet, the less editing you'll need to do afterward. When we added “must fit on a single PowerPoint slide” to our executive summary request, the AI actually delivered something presentation-ready on the first try!
May 7
Ever feel like you're speaking alien to your AI? The “Triple-Vision Translator” hack unlocks clarity at every level. Ask ChatGPT or Claude to explain any complex concept three different ways—for a six grader (or kindergartener, if you want a really simple version), a college student, and a domain expert.
Just copy-paste: “Explain [complex concept] three times: (a) to a 12-year-old (b) to a college student (c) to a domain expert who wants edge-case caveats”
Try it with “neural networks” or “prompt engineering” and watch how the explanations transform. When the simplest explanation doesn’t make sense, you've found your knowledge gap. The stuff you can't explain simply is often the stuff you don't fully understand yourself!
May 8
Here’s a good summary of the above video and how to apply its key takeaways into your own prompts.
May 9
Reddit users have cracked the code on creating “exceptional” resumes that are landing interviews even for positions “way above their level.”
Their secret? Feed ChatGPT your real experiences organized by category (LEADERSHIP, CHALLENGES, TEAMWORK, etc.) along with the job description to generate tailored for STAR-method responses.
If you don’t know, STAR = an interview trick where you tell a story about what happened (story), what you needed to do (task), what you actually did (action), and how it turned out (result). Super helpful for not rambling when they ask about your experience!
Their simple two-step process has hiring managers consistently calling applications "exceptional."
- Step 1: Feed ChatGPT your CV and the job description with this prompt: “Optimize my CV and experience to perfectly match this specific job.”
- Step 2: Use this follow-up: “Give me excellent answers to potential interview questions using my CV and the STAR method with specific examples of how I'm suitable for this role.”
The key? Don't fabricate anything—just organize your authentic experience in a way that precisely matches what employers are seeking.
Interviewers respond dramatically better to applications that speak their language. When you match your genuine experience to their specific needs using AI, you bypass the algorithms and speak directly to the hiring manager's wishlist.
But don't stop there—you can also create a complete AI interview system: use ChatGPT to generate practice questions, conduct mock interviews in voice mode, and even get pre-interview pep talks to calm your nerves.
One user who applied this method went from 151 applications with 6 interviews (and no offers) to 10 applications resulting in 3 interviews and counting (honestly, you should swipe their entire method of job hunting; copy what they wrote on Reddit into GPT and ask it to create a training doc to help you follow their methodology yourself—here’s an example of what we mean, based on this chat)!
Pro tip: For resumes, always humanize the AI output by removing telltale signs like blue headers and excessive bullet points. Also, ask GPT to “dumb down” the writing.
Our favorite IRL insight: Approach your interviews with a “take it or leave it” attitude. Several users reported their best interviews happened when they relaxed after thinking they'd already blown it! If you use these tactics and they help you get a job, let us know!
🧠 Check out the April 2025 Prompt Tips of the Day →
