Five Advisors: The AI Prompt That Argues Back

Before we get started…

If you're the only person in your business who can make the big calls (more on that in a minute), that’s a sign your business is still running on a “YouOS.”

The solution? Upgrade to a custom (and scalable) “operating system” just like the ones we use to scale the companies inside our own $200M portfolio.

If you want to see how it works, check it out here.

Ok, onto this week’s article…

Every business owner has a version of this problem.

You have an idea. A BIG one (maybe even a great one), but it’s too new, too crazy, or too “risky” to share with the team.

Recently, my business partner Richard Lindner shared a prompt that fixes this (hat tip, Richard), and it’s become my new favorite AI prompt.

He calls it "The 5 Advisors,” but I call it my "AI Arguer" because that's exactly what I want it to do: poke holes in my ideas (before the market does it for me).

Check out the prompt (below), and then we can get into how it works:

I know it looks simple, but the output is better than most of the paid advice I’ve invested in over the years, and it’s infinitely better than a roomful of “Yes-men” telling how smart I am.

Let’s break down each "advisor" and why they got an invite to the brainstorming session…

This is your "negative-Nelly." His only job is to tell you why your idea will fail.

He's an obnoxious, paranoid prick, but that's exactly why you NEED him in the room.

Nobody on your payroll will volunteer for this job, because arguing with the owner's favorite idea is a terrible career move. But since this advisor doesn't work for you, he'll say what your team won't.

This one rips up your assumptions, finds the REAL question, and rebuilds the problem from scratch.

Most stuck decisions are stuck because you're attempting to answer the wrong question.

For example, is the question "Should we hire a new agency?" or is the real question, "Is our offer just less appealing than the competition?"

After two rounds of getting beat up, this is the advisor who asks, "Ok, but what if it WORKS?"

Business owners are great at imagining downside and lousy at imagining upside. If the win is asymmetric (small cost if it fails, massive payoff if it hits), you need to know that before you kill the idea out of fear.

He knows nothing about your industry, and that's the point.

Every industry has "rules" that only exist because “That’s how we’ve always done it…” is an acceptable answer in too many organizations.

But sometimes the biggest breakthroughs come from the “new guy” asking, “Wait…why do we do it that way?"

This one doesn't care about strategy or first principles. All he cares about is action and what’s going to happen on Monday morning.

What emails need to be sent? What conversations need to be had? What decisions need to be… decided?

Because ideas don't stall from a lack of strategy. They stall from a lack of ACTION.

STEP 1: Tweak the prompt. Swap the "DECISION I'M STUCK ON" section with the actual decision or question you're wrestling with. Be specific: your numbers, your constraints, and what a "win" looks like. Vague in, vague out.

STEP 2: Let the advisors argue. Paste it into Claude or ChatGPT and let all five respond…in character. (Don’t be surprised if it takes a while. AI enjoys arguing with itself.)

STEP 3: Watch them grade each other. Each advisor reviews the other four responses, anonymized as "Response A," "Response B," and so on.

Just like in the “real world,” when you strip off the labels, the strongest thinking rises to the top, because nobody (including the AI) gets to play favorites.

STEP 4: Let the Chairman make the call. Left to its own devices, AI is a world-class fence-sitter, and every answer concludes with some version of, "On the other hand…"

The Chairman's job is to pick a side: one recommendation, the strongest reason for it, the biggest risk to watch, and your next step for the week.

⚡️ Action Step: Pick the one decision you've been chewing on for more than two weeks and run it through the council today. The whole thing takes about 10 minutes, which is faster and cheaper than calling a company-wide brainstorming session.

Give it a shot and let me know what your council tells you…

-Ryan

Ryan Deiss
Co-Founder and CEO, The Scalable Company

P.S. An AI council can argue with you about the big decisions, but somebody still has to build a business that can execute them without you doing everything.

That's why the first thing we do with every client is install a custom "operating system," so the business runs, grows, and actually pays you…without depending on you for everything.

Click here to see how it works.