Hey, it's Sam.
It's Friday.
We've had a heavy week. We built a Red Team, ran critiques, and synthesized feedback.
Today, I want to end with something simpler.
Let me tell you about the dumbest prompt in my arsenal. And why it's also the most useful.
Why This Matters
Ever been stuck in a prompt battle with an AI?
You've given it all the context. Refined your instructions. Tried three different phrasings.
And the AI keeps giving you the same, bland, uninspired output.
It's stuck. And you're stuck with it.
I used to think the problem was my prompt wasn’t detailed enough.
Turns out, I forgot I was talking to something trained on human conversations.
The Architect's Approach
Sometimes the best way to fix an AI that’s off-track is to talk to it like you would a colleague.
When a creative partner is stuck, you don’t write a 10-page brief. You say, “This isn’t it. Let’s try again.”
I’ve found the same thing works with AI.
When I'm getting bland output, I stop over-engineering and start coaching.
I use a simple, four-word prompt that sounds almost too dumb to work.
"Try again, but harder."
Why This "Stupid" Prompt Works
Sounds ridiculous. But there’s a real principle behind it.
LLMs can get into a groove in a conversation and will continue to generate text that is statistically similar to what came before.
So you give it a detailed rewrite prompt, and it just gives you a more elaborate version of the same bland take.
But “Try again, but harder” throws a wrench in that rhythm.
It doesn’t feed the AI more info. It changes the tone. It snaps the system out of autopilot and nudges it into a different, possibly better direction.
It’s not a strategy. It’s a reset.
A way of saying, “This first draft was lazy. Let’s move past that.”
Today's Action (5 Minutes) 🫵 💥
This one’s fun.
Scroll through your AI chat history. Find a dead conversation where the output just didn’t land.
Just reply to that exact message with: "Try again, but harder."
See what it gives you.
Half the time, it’ll be better.
The other half? Still helpful. You’ll know it wasn’t the effort, It's your inputs or your idea.
Either way, you learn.
Weekend Thoughts
We’ve covered a lot these past two weeks. Foundation. Critique engine. Reset tools.
Next week, we hit the core. How to build killer inputs that run the whole machine.
Have a great weekend.
-Sam
P.S. I’ve used this prompt in client meetings too. When a brainstorm feels dead, I’ll say, “Let’s try again, but harder.” It breaks the politeness filter. Suddenly, people stop tiptoeing and start pushing. Try it Monday.
P.P.S. And yes, it sounds like something your 6th grade PE teacher barked across the field. That’s probably why it works. (Shout out to Coach Washington.)