After testing hundreds of AI prompts, there are a handful that offer results that feel like ChatGPT has read my mind mid-sentence.
These types of prompts aren’t your typical “write a poem for my grandmother” or “summarize this document before my meeting” prompts. They’re weirdly insightful, sometimes unsettling (especially #3) and freakishly effective. I now use them daily to think clearer, work faster and even manage my mood.
Whether I’m stuck on choosing the right tone for a professional email, spiraling over a to-do list or just trying to get out of my own head, these prompts help.
Here are the 5 ChatGPT prompts that feel almost too smart, and how I implement them into my daily life.
1. Changing perspective
Prompt: “If you had to challenge my thinking on this, where would you start?”
This prompt helps you get out of your own head. Whether you’re struggling to come up with more ideas for a project or stressed about an argument with a good friend, this prompt instantly flips your thinking.
By asking this question, you challenge ChatGPT to look for more than what you're currently seeing. Perhaps, you've skipped steps or made assumptions you didn’t realize you were making.
A real-life scenario for this (one I’ve recently used) is uploading screenshots of text messages — removing any personal info — and asking the chatbot to help you see what you’re overlooking in a conversation with a friend. If they just aren'te getting what you're saying, maybe it's you that needs to see something differently.
I’ve also used it to double-check articles, spot gaps in planning and even sanity-check a tough decision.
2. Compassion filter
Prompt: “Now rewrite that for someone who’s completely burned out.”
ChatGPT is getting better at offering empathy, but this prompt encourages it to add some serious understanding. Whether you're writing an email, giving advice or crafting a DM, this forces ChatGPT to soften the language, reduce pressure and acknowledge how the reader might feel, especially when the topic is a senstive one.
I’ve used this when I simply don’t know what to say, but want to say something while showing sincerity. If someone is going through a situation you have never experienced and you’re nervous about saying the wrong thing, this prompt is like a compassion filter.
Recently I used this on myself when I read an article about a CEO’s insane schedule. I gave the productivity tip to ChatGPT and prompted it: “Now rewrite that for someone who’s exhausted.” Me. It’s me.
3. Poke holes in it
Prompt: “Give me 3 unpopular but useful opinions on this.”
Fresh thinking means looking beyond the obvious. Similar to the first prompt, yet different in that this one pushes ChatGPT to surface contrarian ideas to the point where you stop and reconsider your own beliefs. This is an excellent way to improve critical thinking skills and encourage creativity.
Try this prompt when you’re brainstorming and want to gain insight outside of your current views. This even works when you want to understand your own side of things better. Once you have a full view, you’ll be unstoppable when it comes to explaining your ideas.
I use this all the time with many aspects of parenting.
4. Checklist upgrade
Prompt: “Turn this into a checklist I can actually follow.”
A few times when I’ve asked for a checklist, the AI doesn’t consider all aspects of life that might keep me from getting everything done. From kids and pets to unforeseen circumstances, I need flexibility.
This prompt reassures me that the chatbot will break ideas into clear, actionable steps and allow room for things to not go as planned. It’s especially helpful when I'm overwhelmed and just need a path forward.
I’ve used it to turn vague goals into bite-sized tasks. I’ve also used it when I have so much on my plate that I don’t even know where to start. Bonus: it even formats things like a productivity coach would.
5. Everyday advice
Prompt: “If you were me, what would you do right now — and why?”
This one feels a little like therapy, minus the copay. It gives ChatGPT the green light to think like you, based on your situation, and offer input without emotional bias. This is helpful when you really want an honest opinion outside of a friend or family member.
I’ve used it when I’m stuck between two choices or procrastinating on a weekend project. It doesn’t always give the perfect answer, but it almost always helps me clarify my own thinking.
Try it with: “It’s 10pm and I’m stuck between finishing this project or going to bed. If you were me, what would you do?”
ChatGPT will give you the pros and cons to help offer clarity when you need it most.
Bonus tip: Use memory to make these even smarter
If you’ve activated ChatGPT’s memory feature, prompts like these get even better over time. The more context it has about your habits, goals, or tone preferences, the more tailored (and eerily accurate) its responses become.
You can even say: “You know how I like short checklists and empathetic tone? Please keep doing that.” And it will.
Final thoughts
These prompts are simple, but when used well, they create a feedback loop that’s less “robot assistant” and more like a thoughtful thinking partner.
Try one the next time you're stuck and see just how weirdly intuitive the AI gets. I now use them daily to spot mistakes, hack burnout and make decisions faster.
More from Tom's Guide
- Google’s NotebookLM just got a huge upgrade — here’s why it beats ChatGPT for team projects
- I just tested the newest versions of ChatGPT vs Gemini vs DeepSeek vs Claude — and the winner completely surprised me
- The ‘backwards’ prompt that unlocks ChatGPT’s most breakthrough advice
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