ask-questions-if-underspecified

Identify underspecified requests and generate clarifying questions before implementation.

6.5k|561|Updated Jan 14, 2026
One-click install
npx skills add https://github.com/trailofbits/skills --skill ask-questions-if-underspecified-trailofbits
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: ask-questions-if-underspecified
Source: https://github.com/trailofbits/skills/tree/main/plugins/ask-questions-if-underspecified/skills/ask-questions-if-underspecified
Command: npx skills add https://github.com/trailofbits/skills --skill ask-questions-if-underspecified-trailofbits

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

Clarifies ambiguous requests by prompting for targeted clarifying questions before work begins.

Core Features & Use Cases

  • Identifies underspecified objectives, scope, constraints, and safety concerns.
  • Provides a concise set of must-have questions to rapidly resolve ambiguity.
  • Pauses work until essential answers are obtained and confirms interpretation before proceeding.

Quick Start

Ask 1-5 must-have clarifying questions before proceeding with any implementation.

Frequently Asked Questions about ask-questions-if-underspecified

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I clarify ambiguous software requirements before starting implementation?

To clarify ambiguous software requirements, you identify underspecified objectives, scope, and constraints, then generate a focused set of must-have questions to resolve ambiguity before any work begins.

What are essential clarifying questions for underspecified requests in security workflows?

Essential clarifying questions target ambiguous objectives, scope, constraints, environment, and safety considerations across software and security workflows to ensure complete understanding before proceeding.

How do I manage risk when project scope and constraints are not clearly defined?

Risk management for undefined project scope involves pausing work to ask targeted clarifying questions, ensuring all essential answers are obtained and interpretation is confirmed before moving forward.

How many clarifying questions should I ask for an underspecified software engineering task?

For an underspecified software engineering task, you should ask one to five must-have clarifying questions to rapidly resolve ambiguity without overwhelming the requestor.

When do I need to pause work to ask clarifying questions about a request?

You need to pause work to ask clarifying questions whenever a request has ambiguous objectives, scope, constraints, environment, or safety considerations, resuming only after answers are provided and interpretation is confirmed.