// description
Red Team / Blue Team is a structured adversarial exercise where one team (Red Team) attempts to find flaws, vulnerabilities, or counter-arguments in a plan, strategy, or system, while the other team (Blue Team) defends or improves the plan based on the attack. The key distinction from standard critique is that the Red Team's explicit mandate is to be a genuinely adversarial opponent — not to be helpful or diplomatic, but to find every possible weakness as if they wanted the plan to fail. This forces stress-testing against intelligent, motivated opposition rather than the polite critique that most plans receive from friendly reviewers.
// history
Red teaming originated in the U.S. military during the Cold War as a way to stress-test war plans and intelligence assessments by having a dedicated team argue the Soviet position as convincingly as possible. It became institutionalised after intelligence failures — including the Bay of Pigs invasion and the 9/11 attacks — revealed the catastrophic consequences of groupthink in high-stakes planning. In business, red teaming is used in strategy consulting (McKinsey, Bain), product design, and cybersecurity (penetration testing simulates an adversary trying to break in). The CIA and NSA use dedicated red teams to challenge their own assessments and prevent confirmation bias in intelligence analysis.
// example
Before launching a new course, run a solo red team exercise. Take on the adversarial role yourself. Red team questions: "Who would actively not want this course and why?" "What would make a potential student choose a competitor over me?" "If this launch fails, what's the single most likely reason?" "What's the weakest part of my sales argument — the thing I'm glossing over because I don't want to think about it?" "What would a cynical journalist write about this offer?" Answer each honestly. Then switch to blue team: how do you address each vulnerability before launch day? Which ones can be fixed, and which represent genuine risks you need to price in?
// katharyne's take
Red teaming your own launches is one of the highest-value pre-launch activities you can do — and it's basically free. The discipline is forcing yourself to genuinely argue against your own plan, not just acknowledge obvious weaknesses. The question "if I were a competing creator, how would I position against this offer?" has changed several of my launch strategies. You can also do this with a trusted peer — take turns red-teaming each other's plans. Two brain cells are dramatically better than one for finding the holes.
// creative uses
- Red team your Etsy or KDP listing before you publish it: act as a sceptical buyer. What in the listing is unclear? What would make you hesitate to buy? What does the competition offer that this listing doesn't address? Fix every issue the red team surfaces before you go live — it costs nothing and directly improves conversion rates.
- Run a red team exercise on your pricing strategy: what arguments would a customer make for not paying your price? What would a competitor use to position against you on price? The answers reveal objections you need to pre-empt in your sales copy and whether your price is genuinely defensible or just hopeful.
- Use red teaming as a community or mastermind activity: pair members and have them take turns red-teaming each other's current projects for 15 minutes each. The structured adversarial framing produces more useful feedback than "what do you think of my idea?" — and it's a high-retention activity because it creates real value for every participant.
// quick actions
- Pick the project you're most excited about right now and spend 20 minutes genuinely red-teaming it: write down every reason it could fail, every objection a buyer might have, and every advantage a competitor has over it. Do not soften anything. Then write one paragraph on which of those vulnerabilities you can fix before launch.
- Find one trusted peer in your field and propose a red team exchange this week: each of you attacks the other's current plan for 15 minutes, then switches roles. The reciprocal structure removes the social awkwardness of asking someone to criticise your work.
- Red team your top-performing product's sales page as if you were a buyer encountering it for the first time with no prior knowledge of you — note every moment of confusion, doubt, or unmet question. Each one is a conversion leak you can fix with one editing session.
// prompt ideas
Red team my upcoming [course launch / product launch / niche entry]. Take on the role of a motivated adversary who genuinely wants this to fail — a sceptical buyer, a competing creator, or a cynical journalist. Generate 10 specific, honest attacks on my plan: weak points in the offer, objections in the sales argument, competitor advantages I'm ignoring, and risks I'm underweighting. Don't soften anything. Then switch to blue team and tell me which of those attacks I can actually address before launch.
Red team my [Etsy listing / KDP book page / sales page] as a first-time visitor who knows nothing about me and has three competing options in the same search results. Here's the listing: [paste it]. Attack it like a buyer who is looking for reasons not to buy: what is unclear, what creates doubt, what does the competition do better, and where does the page lose trust? Then give me a prioritised list of the three most conversion-damaging issues to fix first.
I want to run a red team / blue team exercise in my [mastermind / community / course cohort]. Design a 30-minute facilitation guide for pairs: how to assign red and blue team roles, what red team questions to use as prompts, how to structure the 15-minute attack phase without it becoming unhelpful, and how to transition into the blue team improvement phase. The context is creators reviewing each other's [product ideas / launch plans / business models].