The 21 Hats Morning Report

The 21 Hats Morning Report

The Magic Question to Ask ChatGPT

Alan Pentz says AI can be incredibly smart and incredibly dumb at the same time. But it can become your secret weapon if you know how to talk to it.

Loren Feldman's avatar
Loren Feldman
Jul 30, 2025
∙ Paid

Good Morning!

Here are today’s highlights:

  • Ninety-seven percent of U.S. businesses that import products are small businesses. Some of them are running out of options.

  • Trump is winning his trade war negotiations. What will that mean for the U.S. economy?

  • The economy returned to growth in the second quarter.

  • Today’s question: Does it matter if your business coach was a failure as a business owner?

ARTIFICIAL INTELLIGENCE

Alan Pentz offers some advice on prompting ChatGPT: “Ever asked ChatGPT for business advice and gotten something that sounds like it was written by someone who learned about business from a textbook? ‘Leverage your core competencies to create synergistic value propositions...’ Cool story but how do I get more customers? Here's the thing about AI that took me way too long to figure out: It's incredibly smart and surprisingly dumb at the same time. Like that friend who can solve complex math problems but can't talk to a girl. The good news? Once you know how to talk to it, AI becomes your secret weapon. The trick isn't getting fancier AI—it's getting better at asking for what you need.”

  • “Be Specific (Like, Really Specific). Instead of: ‘Help me with marketing.’ Try: ‘Write 3 Instagram posts for my coffee shop that make people want to visit on a rainy Tuesday. Target remote workers. Make it funny but not trying-too-hard funny.’ See the difference? One gets you generic fluff. The other gets you something you can actually use.”

  • “Set the Scene Like You're Briefing a New Employee: AI doesn't know your business exists. So tell it. Who actually buys from you (hint: ‘everyone’ is not an answer)? What makes you special (and please don't say ‘customer service’)? How do you actually talk (formal? casual? somewhere in between?)?”

  • “Quick example: ‘I run a pet grooming business. My clients are mostly busy professionals who treat their dogs like children. I'm the expensive option but worth it because they want to know their dog is treated like royalty.’”

  • “The Magic Question Hack: Before diving into solutions, try this game-changer: ‘Before answering, what are 3 things you need to know about my situation to give me actually useful advice?’ This turns AI from a know-it-all into a consultant who actually listens.” READ MORE

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