Most people use Claude to make their business sound good. The smarter move is the opposite: have it attack your business and show you where it's about to break. It's called red teaming, you point the AI at your own weak spots on purpose, and it finds the holes before a customer or a competitor does.

The best part is it's blunt in a way real people rarely are to your face. Here are the two prompts from the video, word for word, plus 10 more. Run each one, then paste in what you sell and who you serve so it has the context to be specific. Every prompt below has a Copy button, so just grab it and go.

The 2 prompts from the video

1. The breakup email

This writes the honest cancel email a frustrated customer would actually send you, the one they think but never type into your polite feedback form.

The prompt
You are a customer who used my product for six months, liked it at first, and just canceled. Write me the breakup email, emotionally honest, the version you'd text a friend, not the polite feedback form.

Here is what I sell and who I serve: [paste it in].

2. The ruthless competitor

This hands you the exact game plan a competitor would run to take your customers, so you can defend against it before they ever start.

The prompt
You're my most ruthless competitor. Build the exact plan you'd use to steal my customers in 12 months. Be specific about the angle you'd attack, the messaging you'd use, and where I'm weakest.

Here is what I sell and who I serve: [paste it in].

10 more red team prompts

Same idea, different angle of attack. Paste your business context into each one.

3. The churn autopsy

Surfaces the quiet cancels, the people who leave without ever telling you why.

The prompt
List the top 5 reasons a customer quietly cancels on me without ever saying why, ranked by how common they are. For each one, tell me the earliest warning sign I would see before they go.

Here is what I sell and who I serve: [paste it in].

4. The honest 1-star

The fair but damaging review that makes other buyers hesitate.

The prompt
Write the most damaging but completely fair 1-star review a real customer could leave me. Make it specific, the kind that makes other buyers hesitate before they purchase.

Here is what I sell and who I serve: [paste it in].

5. The skeptical prospect

The objections you fumble on sales calls, and what would actually win the deal.

The prompt
You're a sharp prospect on a sales call with me. Hit me with the 5 hardest objections I probably fumble, and for each one tell me what I would actually need to say to win you.

Here is what I sell and who I serve: [paste it in].

6. The price attack

Every reason a buyer decides you're too expensive, and how to kill it.

The prompt
List every reason a buyer decides I'm too expensive or not worth it. Then tell me exactly what I'd have to change about my offer to kill that objection.

Here is what I sell and who I serve: [paste it in].

7. The single point of failure

The one thing that would hurt most if it broke tomorrow.

The prompt
What is the one thing in my business that, if it broke tomorrow, would hurt the most? Show me how it breaks, and what I'm not doing right now to prevent it.

Here is what I sell and who I serve: [paste it in].

8. The well-funded new entrant

A funded startup launches to take your market. What's their plan?

The prompt
A well-funded startup is launching to take my exact market. Write their launch plan and their first ad. Be specific about what they attack about me and how they position against me.

Here is what I sell and who I serve: [paste it in].

9. The wavering loyalist

Your best customer has quietly started looking around. Why?

The prompt
You're my best customer, but you've quietly started looking around. Tell me honestly what's making you consider leaving, even though you still mostly like me.

Here is what I sell and who I serve: [paste it in].

10. The exit interview

What a sharp employee who just quit would say is actually broken.

The prompt
You're a sharp employee who just quit. Write the honest exit interview about what's actually broken in how this business runs day to day, the stuff no one says out loud.

Here is what I sell and who I serve: [paste it in].

11. The trust gap

What's quietly costing you sales before anyone even talks to you.

The prompt
What about my brand, my site, or my offer makes a first-time buyer not trust me yet? List what's quietly costing me sales before anyone even talks to me.

Here is what I sell and who I serve: [paste it in].

12. The closed tab

The real reason someone almost bought and then didn't.

The prompt
You almost bought from me but didn't. Tell me the real reason you closed the tab, and the one thing that would have changed your mind.

Here is what I sell and who I serve: [paste it in].

How to actually use these

Three things make the difference between a useless answer and a scary-accurate one:

  • Give it real context. Paste in what you sell, who it's for, your price, and your main promise. The more it knows, the sharper the attack.
  • Don't argue with it. The instinct is to defend yourself. Resist it. Let the uncomfortable answer sit, that's the whole point.
  • Fix one thing. Each prompt usually surfaces one obvious hole. Patch that before you run the next. Ten insights you ignore beat nothing, but one you act on beats all ten.
Your business has blind spots you literally cannot see, because you're standing inside it. These prompts borrow an outside set of eyes that has no reason to be nice to you. Use them before your customers and competitors do it for free.

Run one of these tonight on your own business. The answers sting, and that's exactly why they're worth it.
– Anir

If this is the kind of AI thinking you want working on your own business, apply to work with me. And to catch the next breakdown, join the newsletter.