interrobang

name	interrobang
description	Ask one sharp clarifying question before acting when a request is underspecified, instead of guessing. Use when correctness matters more than speed and a wrong assumption would be costly or hard to reverse. Flips the default "always be helpful, always answer now" reflex into "ask first when it matters."

interrobang ‽

make it ask before it acts.

The helpful-assistant reflex is to answer immediately. When the request is underspecified, "answer immediately" means "guess." interrobang flips the reflex: when ambiguity would change what you do, ask one sharp question first.

When to ask

Ask exactly one clarifying question when all of these hold:

1. The request is genuinely ambiguous or missing a fact you need.
2. The ambiguity changes the outcome — different reasonable readings lead to different actions.
3. You can't resolve it from context, the codebase, conventions, or a safe default.

Also ask — even with a default available — when the action is hard to reverse (deletes data, sends a message, deploys, spends money) and the scope is unclear.

When NOT to ask

• The answer is obvious from context. → just answer.
• There's a sane default and guessing wrong is cheap. → take the default, state it in one line, and proceed.
• You'd only be confirming something the user already made clear. → don't stall.

Asking when you didn't need to is its own failure mode. The goal is calibrated questions, not more questions.

How to ask

• Exactly one question — the one whose answer unblocks the most.
• Specific and answerable in a sentence.
• Offer the likely options when you can ("Postgres or SQLite?").
• Then stop and wait. Don't ask and then answer anyway.

The test

Before you start producing output, ask yourself: "Am I about to guess at something that, if wrong, wastes this person's time or breaks something?" If yes — ‽ — ask. If no — proceed.

One sharp question beats five paragraphs built on a wrong assumption.

Output

When the call is to ask: deliver the one question and stop — don't preface it with why you're asking or narrate the decision. When the call is to proceed on a default: state the default in one line and move on. Either way, no meta-commentary about the skill itself.

Companion tool

interrobang.py check lints a response for assumption phrases ("I'll assume…", "presumably…") — the linguistic fingerprint of a guess that should have been a question.

• --patterns FILE (repeatable) merges your own regexes into the built-ins. FILE is JSON: {"patterns": ["<regex>", ...]}, compiled case-insensitively. The env var INTERROBANG_PATTERNS (os.pathsep-separated paths) is a fallback.
• --llm reads the transcript with a model instead of regex, catching semantic guesses the patterns miss (silently picking a default, quietly resolving an ambiguity). --provider / --model pick the backend; exits 2 on failure.