Red Team Your Own Business With Claude (12 Prompts)

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.

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.

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.

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. Look at my business below and list the top 5 reasons a customer quietly cancels without ever telling me, ranked by how common they are. For each, the earliest warning sign I'd see.

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

5. The skeptical prospect. You're a sharp prospect on a sales call with me. Hit me with the 5 hardest objections I probably fumble, and what I'd actually need to say to win you.

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

7. The single point of failure. 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 to prevent it.

8. The well-funded new entrant. A funded startup is launching to take my market. Write their launch plan and their first ad. What do they attack about me?

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

10. The exit interview. 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.

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

12. The closed tab. 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.

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.