Pre-mortem prompt: stress-test a feature before you ship it
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Pre-mortem prompt: stress-test a feature before you ship it A pre-mortem prompt that assumes a feature has already failed and works backwards to surface adoption, technical, second-order and business risks before you build it. Great for product decisions with ChatGPT or Claude.
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It's [6 months] after we shipped [feature name]. It failed. Not a small stumble, it's being rolled back, quietly killed, or has become a liability we regret. Assume this as fact and work backwards.
Here's the feature: [1-3 sentence description, who it's for, and the core value prop].
Walk me through what went wrong across these angles:
Adoption: why didn't people use it, or use it the way we hoped? What did we assume about user motivation or behavior that turned out to be wrong?
Discoverability & onboarding: how did users fail to find it, understand it, or get to first value?
Technical & operational: what broke, degraded, or didn't scale? What edge cases, data issues, or integration failures bit us?
Second-order effects: what did it break elsewhere? Did it cannibalize another feature, confuse the product's story, create support load, or invite abuse?
Business & metrics: did it move the wrong number, or move the right number the wrong way? Did we measure the wrong thing and declare false success?
The thing nobody said out loud: what concern did people privately have that we talked ourselves out of?
For each failure mode: state the specific mechanism (not "users didn't like it" but why), rate its likelihood (high/med/low) and how early we'd see the warning signs, and give one concrete thing we could do now to prevent or de-risk it.
Be blunt. I want the uncomfortable version, not the diplomatic one.
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