The 21 Hats Morning Report

The 21 Hats Morning Report

How to Build a Board of Super-Smart Advisors

Sean Campbell's panel features eight perspectives, including an operator who asks if the plan can be executed, a CFO who runs the numbers, and a contrarian who challenges the consensus.

Loren Feldman's avatar
Loren Feldman
Apr 23, 2026
∙ Paid

Good morning!

Here are today’s highlights:

  • Here’s why a CEO interviews job candidates on Sundays.

  • The Harvard Business Review says brick-and-mortar is back.

  • Cocktail inflation is boosting a trend known as pregaming.

  • Businesses remain skeptical that the Trump administration will refund their money.

MANAGEMENT

Sean Campbell explains how he created a board of advisors: “One of the strategies I’ve been using for a significant amount of time is treating AI as a genuine thinking partner for the decisions that actually matter. Not a tool that gives you answers. A collaborator that challenges your assumptions, pressure-tests your logic, and asks the uncomfortable questions your inner circle probably won’t. Most people haven’t gotten there yet. They’re still in ‘ask a question, get an answer’ mode. And that’s fine for everyday tasks. But when you’re facing a decision where being wrong costs years, not hours, you need something more structured. You need AI that pushes back.”

  • “I created what I call a Decision Panel. It’s an AI-powered framework that puts my thinking in front of eight distinct expert perspectives, each designed to challenge me from a different angle. Not eight versions of the same helpful AI assistant. Eight genuinely different lenses. An Operator who asks if I can actually execute the plan. An Investor watching opportunity cost. A CFO running the downside math. A Career Coach asking what kind of life I’m building. A Contrarian who argues the opposite of whatever the consensus is. A Customer who asks whether anyone would actually pay for the idea. A Technologist evaluating whether it survives the next platform shift. And a Pastor/Theologian who asks whether I’m deciding from faith, fear, and whether the decision I’m considering aligns with the values I believe in.”

  • “After all eight weigh in, I get a synthesis that maps where they agree, where they disagree, and the strongest challenges to my current leaning. Not a vote. A reasoned integration that surfaces the tensions I need to sit with before I decide.”

  • “This is the difference between using AI and collaborating with AI. If you just ask ‘should I take this opportunity?’ you’ll get a diplomatic answer that reads well and helps very little. The Decision Panel works because each expert has a defined role, a clear worldview, and specific instructions to challenge rather than confirm.” READ MORE

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