As we approach year-end, my thoughts have been on finishing strong and planning for a great 2026.
Last week, we looked at a prompt that created a new keystone habit. This week, I’m sharing another simple prompt that I found valuable and insightful. It’s designed to review your conversation history, conduct a mini-assessment, and give you a glimpse into your blind spot.
Like last week’s prompt, as written, it’s somewhat generic and might hallucinate a little if it doesn’t have enough data. That’s easy to fix by improving the prompt. But for the purposes of getting started, this is good enough.
Here is the base prompt to try in your primary AI tool.
“ From all of our interactions, what is one thing that you can tell me about myself that I may not know about myself?”
Sometimes, less is more.
There are lots of ways to use something like this. For example, you can tell it to be “brutally honest” or to “roast you” so that you hear it in humorous terms. With that in mind, here are a bunch of copy/paste prompt variants that produce the same kind of “surprising but grounded” self-insight, each from a different angle.
Pattern + Blind Spot Variants
- Strength-with-a-Shadow
From our interactions, name one strength I clearly have and the most likely downside of that strength when overused. Give 2 examples from our chats and 1 practical guardrail.
- Default Operating System
What is my “default mode” behavior, under pressure, based on our interactions? What does it protect me from, and what does it cost me?
- Hidden Constraint
Identify one hidden assumption I seem to carry. Explain how it helps me, how it limits me, and one experiment to test it.
- Blind Spot That Looks Like a Virtue
What’s a behavior of mine that most people would praise, but that could quietly create problems? Be specific and non-psychological.
Decision-making + execution variants
- Where I Over-Engineer
Where do I tend to add unnecessary complexity? Give one example pattern, why I do it, and a “2-step simplification rule” I can apply.
- Where I Under-Commit
Based on our interactions, where might I stay in analysis longer than needed? Give a “commitment trigger” and a script for making the decision.
- One Question I Avoid
What is one question I rarely ask, but should, given my goals? Provide the exact wording and when to use it.
- My “Next Constraint”
If I had to improve only one constraint in my system (time, focus, delegation, communication, risk), which one is highest leverage and why?
Communication + Relationships Variants
- How I’m Experienced by Others
Based on my writing and requests, how might teammates/investors experience me on a good day vs a stressed day? Give 3 traits each and 1 calibration move.
- Trust Friction
Identify one way my communication style could unintentionally reduce trust or clarity. Give a rewrite pattern I can apply.
- Authority vs Warmth Dial
Where do I sit on the authority↔warmth spectrum in my messages? What’s the risk at my current setting, and how do I adjust without becoming fake?
Energy + Focus Variants
- My Energy Signature
Infer my likely “energy curve” and where I do my best thinking. Give a schedule template that matches it and one rule for protecting it.
- My Procrastination Costume
What form of “productive procrastination” do I use (based on our chats)? Give a 60-second interrupt and a 10-minute re-entry plan.
Identity + Growth Variants (Grounded, Non-Therapy)
- My Core Values in Disguise
What values do my patterns suggest (not what I claim)? Give 3 values, the evidence, and one way each can be expressed more cleanly.
- My Edge
What’s one capability I’m unusually strong at that I might be underpricing? Give one way to productize it and one way to teach it.
Tighter “One Thing” Variants
- One Sentence, Then Proof
Tell me one thing about myself I might not know in a single sentence. Then justify it with 3 specific signals from our interactions and 1 counter-signal.
- If-Then Insight
If I keep doing X, then Y will happen (good and bad). Identify X and Y from our interactions, and give one small change.
- The Uncomfortable Gift
Give me one insight that’s slightly uncomfortable but genuinely helpful. Be kind, direct, and practical. End with one question for me.
Hopefully, you found something that helped you find what you were looking for.
It’s a good reminder that AI is not supposed to replace you … It’s supposed to amplify the best parts of you.
A lot of these exercises and thought patterns are based on activities I used to do in my own planning, or with trusted advisors. As I use AI more in my everyday life, it has collected enough data to be a powerful analysis tool (and that is a scary reminder of how much it knows and remembers).
I believe in examining your thinking – and using those insights to choose smarter and better actions. Prompts like this are a powerful tool for building that habit … but only if you remember that it is still you choosing and acting!
Don’t outsource what makes you human to the machines … but that doesn’t mean you can’t use a helping hand.
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