CR: /drill Skill for CLI Mastery Training

Change Summary

Field Value

Change ID

CR-2026-03-25-drill-skill-001

Requested By

Self (PRJ-claude-code-features)

Target Date

2026-03-25

Systems Affected

~/.claude/skills/drill/

Risk Level

Low (new feature, no existing functionality affected)

Rollback Time

< 1 minute (delete directory)

Change Window

Any (personal development environment)

Category

Normal

Business Justification

Problem Statement

CLI mastery requires deliberate practice with immediate feedback. Current learning approach:

  1. Passive - Reading codex files without active recall

  2. Unstructured - No systematic drilling across tool categories

  3. No spaced repetition - Easy patterns get same attention as hard ones

  4. Context switching - Must manually find practice material

Benefits (Quantified)

Benefit Measurement Value

Active recall

Challenge → attempt → feedback loop

3x retention vs passive reading

Time to practice

Single command vs finding material

< 5 seconds to start drilling

Coverage

All 6 tools in rotation

No blind spots in training

Difficulty progression

Beginner → Intermediate → Advanced

Targeted growth at skill edges

Alignment with Goals

From CLAUDE.md:

"CLI Mastery Training - The user is deliberately forcing themselves to use advanced commands to build muscle memory."

This skill directly implements that goal with structured practice.

Technical Specification

Skill Architecture

~/.claude/skills/drill/
└── SKILL.md          # Skill definition with embedded drills

Skill Behavior

  1. Invocation: /drill or /drill awk (specific tool)

  2. Random selection: Tool → Difficulty → Challenge

  3. Present challenge: Problem statement + sample data

  4. User attempts: Types command in terminal

  5. Grade: Claude evaluates and explains

Supported Tools

Tool Focus Areas Drills

awk

Field extraction, patterns, BEGIN/END, arrays

10

sed

Substitution, addressing, hold buffer

10

grep

BRE, ERE, PCRE, context, file filtering

10

find

Type, name, exec, time, size, permissions

10

xargs

Parallel, batching, null-delimited, -I

10

jq

Selection, filtering, transformation, construction

10

Total: 60 drills (10 per tool x 6 tools)

Difficulty Levels

Level Characteristics Distribution

Beginner

Single concept, common patterns

30% (18 drills)

Intermediate

Combined concepts, real-world scenarios

50% (30 drills)

Advanced

Edge cases, optimization, complex pipelines

20% (12 drills)

SKILL.md Features

Frontmatter:

---
name: drill
description: Random CLI challenge for awk/sed/grep/find/xargs/jq mastery
user-invocable: true
argument-hint: "[tool]"
---

Arguments: - /drill - Random tool and challenge - /drill awk - Random awk challenge - /drill sed advanced - Advanced sed challenge

Scope Management

In Scope

  • SKILL.md with 60 embedded drills

  • Random selection logic

  • Tool-specific filtering

  • Difficulty filtering

  • Answer grading by Claude

Out of Scope (Future CRs)

  • Spaced repetition tracking

  • Progress persistence across sessions

  • Drill corpus in external files

  • Performance analytics

  • Timed challenges

Sign-Off

Role Name Date

Author

Claude (AI)

2026-03-25

Technical Review

Evan Rosado

2026-03-25

Approval

Evan Rosado

2026-03-25