Fix AI's Overconfidence with One Trick


AI is everywhere right now. Every day, there's a new tool, a new headline, a new promise that AI will revolutionize your business.

But here's what we learned from working with 52 companies over the past month in the Second Brain Enterprise beta cohort: AI doesn't solve business problems—it exposes them.

The businesses winning with AI aren't the ones with the best tools.

They're the ones who understand their operations clearly enough to know where AI can actually help.

Most companies are trying to add AI to chaos and wondering why it's not working.

On July 16th, I will teach the core frameworks that help you see your business clearly first—before you automate anything.


How to Stop Burning $250K on Every Bad Hire (AI for Business Deep Dive)

Most businesses are unknowingly burning thousands every month because they don’t have measurable KPIs or a systematic hiring process.

But to thrive, every employee needs clarity on…

  • where the company is going
  • what their role is and how it’s contributing to the overall goal
  • how their success is measured

In this video, serial entrepreneur Hayden Miyamoto and I show you how to leverage Claude for creating KPIs and complete hiring packages, saving you days of work.

This is part 3 of our Master Prompt YouTube series, where we help you build an AI-powered operating system for your business.


Fix AI's Overconfidence with One Trick

I discovered a technique through this Substack post that helps us work with one of AI's biggest flaws: everything sounds completely certain.

Think about human conversations. We show uncertainty through tone, facial expressions, and phrases like "I think" or "maybe." This uncertainty is valuable information that helps us evaluate advice.

AI has none of this. It presents every suggestion with 100% confidence, making it hard to know what to trust or validate further.

The solution: Add this simple protocol to your personal preferences so it becomes part of every AI response:

Add a section at the end of your responses labeled "Uncertainty Map," where you describe what you're least confident about, what you may be oversimplifying, and what questions or followups would change your opinion.

I've been using this technique, and it's transformed how I work with AI. Instead of taking everything at face value, I now get advance warning about which parts need more validation, which are opinion-based, and where the AI might be wrong.

Your turn: Try adding this protocol to your next AI conversation. Reply and let me know what you discovered when you asked AI to show its uncertainty.


The Chief of Staff for Your Email

My friend Dan Shipper, co-founder of Every, just announced that their new email app, Cora, is finally out of private beta and available publicly.

Cora will…

  • Screen your emails so you only see the 20% that matter
  • Draft responses in your voice
  • Turn 80% of your inbox into a brief you can read in 30 seconds

You can also chat or email with it like a human and it will remember everything you ask for.

(Even if you’re not on the market for a new email app, you might still appreciate the unique design of the landing page.)


Make Time for Big Ideas

I still love learning from books. But after having kids, carving out hours to read just isn’t realistic anymore.

That’s why I’ve been leaning on Shortform — it gives me deep, thoughtful summaries of top nonfiction books, without cutting corners on substance.

You’ll find titles like Feel Good Productivity by Ali Abdaal and Four Thousand Weeks by Oliver Burkeman, plus a growing library covering everything from career and psychology to leadership and creativity.

What makes Shortform great:

  • Expert breakdowns and insights
  • Related ideas and counterpoints from other books
  • Audio + print formats
  • Exercises to apply what you’ve learned
  • Shortform goes beyond book guides. It also included are article and podcast guides.

The first 500 of my readers get 20% OFF an annual subscription and a free trial.

Thanks to Shortform for sponsoring this newsletter.

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Tiago Forte

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