Verified:GitHub

deep-ask

Clarify ambiguous tasks through context-aware progressive questioning.

Updated Aug 23, 2026

Search Tags:#decision making #problem solving #requirements #clarification #interactive #human-in-the-loop #contextual ai

One-click install

npx skills add https://github.com/lnittman/skills --skill deep-ask

Or copy as Structured Prompt for Agent▼

Please help me install this Agent Skill.
Skill: deep-ask
Source: https://github.com/lnittman/skills/tree/main/skills/deep-ask
Command: npx skills add https://github.com/lnittman/skills --skill deep-ask

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill requires layer, outline, git, linear, slack, and includes references (resource) components.

What problem does it solve?

Ambiguous tasks and unclear requirements lead to wasted effort, rework, and frustration. This skill transforms vague requests into precise, actionable specifications through intelligent, context-aware, and progressive questioning.

Core Features & Use Cases

Context-First Questioning: Automatically gather relevant codebase, CLI, and historical context before asking, avoiding redundant questions.
Layered Question Flows: Chain questions dynamically, building on prior answers to progressively refine understanding and explore implications.
Tool-Enhanced Discovery: Use CLI tools mid-flow to verify user mentions and ask more informed, precise questions based on real-time data.
Meta-Questioning: Periodically step back to reveal unstated constraints, identify missing information, and ensure overall alignment with user intent.

Quick Start

Help me think through the architectural trade-offs for a new feature, starting with the core problem we're solving.