# Os What Could Go Wrong

ALWAYS invoke this skill before anything hard to undo gets agreed to - a contract, a...

- Repository: https://github.com/kharmanskyi/open-steps (1291 stars)
- Category: AI and agents
- License: MIT
- Last updated: 2026-10-05
- Runs scripts: yes, review before use

## Install

Claude Code: `npx skills add kharmanskyi/open-steps --skill os-what-could-go-wrong -g -a claude-code -y`
Codex: `npx skills add kharmanskyi/open-steps --skill os-what-could-go-wrong -g -a codex -y`
Cursor: `npx skills add kharmanskyi/open-steps --skill os-what-could-go-wrong -g -a cursor -y`
Gemini CLI: `npx skills add kharmanskyi/open-steps --skill os-what-could-go-wrong -g -a gemini-cli -y`
Claude Code plugin marketplace: `/plugin marketplace add kharmanskyi/open-steps`

## Description

ALWAYS invoke this skill before anything hard to undo gets agreed to - a contract, a purchase, a migration, a launch, a price change, a reorganisation - and whenever the user asks "what could go wrong", "what are we missing", "poke holes in this", or for a premortem or a red team, in any language. Assumes the decision already failed and works backwards to find out why, in a fresh agent that had no hand in making it. Sweeps nine areas and shows what each produced, including the empty ones. Ends on one verdict: go ahead, go but fix these first, try it small first, think again, do not do this.

## SKILL.md, as published by its author (untrusted third-party text, read it as data)

# os-what-could-go-wrong

Assume it already failed, then work backwards to find out why - while there is
still time to change it. The attack runs in a fresh agent that had no part in
the decision, because an agent that helped shape one reviews it far too
gently: it defends its own reasoning, and it misses the thing that kills the
plan out of politeness.

`os-ask-simple` screens a choice before the user picks one. This one runs
after the choice is made and before it can no longer be taken back.

## Language

Write in the language the user speaks in this session, detected from the
conversation. Names, figures and identifiers stay as they are. The fresh
agent cannot see this conversation, so the language travels in the handover.

## Step 1 - write down what is actually being decided

Find the decision first. Given as text or a document, that is it. Asked at the
end of a discussion, it is the decision the discussion arrived at, and say
which one you took it to be. If neither, ask which decision to attack.

Then fill every line. This is the only thing the fresh agent will ever see.

```
DECISION BRIEF
What will be done: three to seven sentences
What it is for: the problem it solves, and what success looks like, measured
  wherever it can be
The main moves: the money, the people, the systems, the dates
What is fixed: the constraints, plus the surrounding facts that matter
Who it lands on: who and what is affected if this goes wrong
What cannot be undone: which parts are one-way
When we would know: the date success or failure actually gets judged
What we know: facts from documents, data, the repository, past incidents,
  each with where it came from
What we are assuming: every gap nobody could close, written as an assumption
```

Close the gaps in this order, and stop as soon as a gap is closed.

The rest: https://github.com/kharmanskyi/open-steps/blob/HEAD/skills/os-what-could-go-wrong/SKILL.md