absolutelyskilled/cli-design

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CLI Design

CLI design is the practice of building command-line tools that are intuitive, composable, and self-documenting. A well-designed CLI follows the principle of least surprise - flags behave like users expect, help text answers questions before they are asked, and errors guide toward resolution rather than dead ends. This skill covers argument parsing, help text conventions, interactive prompts, configuration file hierarchies, and distribution strategies across Node.js, Python, Go, and Rust ecosystems.

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When to use this skill

Trigger this skill when the user:

• Wants to build a new CLI tool or add subcommands to an existing one
• Needs to parse arguments, flags, options, or positional parameters
• Asks about help text formatting, usage strings, or man pages
• Wants to add interactive prompts, confirmations, or selection menus
• Needs to manage config files (dotfiles, rc files, XDG directories)
• Asks about distributing a CLI via npm, pip, cargo, brew, or standalone binary
• Wants to add shell completions (bash, zsh, fish)
• Needs to handle stdin/stdout piping and exit codes correctly

Do NOT trigger this skill for:

• GUI application design or web UI - use frontend or absolute-ui skills
• Shell scripting syntax questions unrelated to building a distributable CLI tool

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Key principles

1. Predictability over cleverness - Follow POSIX conventions: single-dash short flags (-v), double-dash long flags (--verbose), -- to end flag parsing. Users should never have to guess how your flags work.

2. Self-documenting by default - Every command must have a --help that shows usage, all flags with descriptions, and at least one example. If a user needs to read external docs to run a command, the help text has failed.

3. Fail loudly, recover gracefully - Print errors to stderr, not stdout. Use non-zero exit codes for failures. Include the failed input and a suggested fix in every error message. Never fail silently.

4. Composability - Respect the Unix philosophy: accept stdin, produce clean stdout, use stderr for diagnostics. Support --json or --output=json for machine-readable output so other tools can pipe it.

5. Progressive disclosure - Show the simplest usage first. Hide advanced flags behind --help subgroups or separate help <topic> commands. New users see 5 flags; power users discover 30.

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Core concepts

Argument taxonomy

CLI arguments fall into four categories that every parser must handle:

| Type | Example | Notes | |------|---------|-------| | Subcommand | git commit | Verb that selects behavior | | Positional | cp source dest | Order-dependent, unnamed | | Flag (boolean) | --verbose, -v | Presence toggles a setting | | Option (valued) | --output file.txt, -o file.txt | Key-value pair |

Short flags can be combined: -abc equals -a -b -c. Options consume the next token or use =: --out=file or --out file.

Config hierarchy

CLIs should load configuration from multiple sources, with later sources overriding earlier ones:

1. Built-in defaults (hardcoded)
2. System config   (/etc/<tool>/config)
3. User config     (~/.config/<tool>/config or ~/.<tool>rc)
4. Project config  (./<tool>.config.json or ./<tool>rc)
5. Environment vars (TOOL_OPTION=value)
6. CLI flags       (--option value)

Exit codes

| Code | Meaning | |------|---------| | 0 | Success | | 1 | General error | | 2 | Misuse of command (bad flags, missing args) | | 126 | Command found but not executable | | 127 | Command not found | | 128+N | Killed by signal N (e.g. 130 = Ctrl+C / SIGINT) |

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Common tasks

1. Parse arguments with Node.js (Commander.js)

Define commands declaratively and let Commander handle help generation.

import { Command } from 'commander';

const program = new Command();

program
  .name('mytool')
  .description('A CLI that does useful things')
  .version('1.0.0');

program
  .command('deploy')
  .description('Deploy the application to a target environment')
  .argument('<environment>', 'target environment (staging, production)')
  .option('-d, --dry-run', 'show what would happen without deploying')
  .option('-t, --tag <tag>', 'docker image tag to deploy', 'latest')
  .option('--timeout <ms>', 'deploy timeout in milliseconds', '30000')
  .action((environment, options) => {
    if (options.dryRun) {
      console.log(`Would deploy ${options.tag} to ${environment}`);
      return;
    }
    deploy(environment, options.tag, parseInt(options.timeout, 10));
  });

program.parse();

2. Parse arguments with Python (click)

Click uses decorators for commands and handles type conversion, help generation, and shell completions out of the box.

import click

@click.group()
@click.version_option("1.0.0")
def cli():
    """A CLI that does useful things."""
    pass

@cli.command()
@click.argument("environment", type=click.Choice(["staging", "production"]))
@click.option("--dry-run", "-d", is_flag=True, help="Show what would happen.")
@click.option("--tag", "-t", default="latest", help="Docker image tag.")
@click.option("--timeout", default=30000, type=int, help="Timeout in ms.")
def deploy(environment, dry_run, tag, timeout):
    """Deploy the application to a target environment."""
    if dry_run:
        click.echo(f"Would deploy {tag} to {environment}")
        return
    do_deploy(environment, tag, timeout)

if __name__ == "__main__":
    cli()

3. Add interactive prompts

Use prompts for destructive actions or first-time setup. Never force interactivity - always allow --yes / -y to skip prompts for scripting.

import { confirm, select, input } from '@inquirer/prompts';

async function interactiveSetup() {
  const name = await input({
    message: 'Project name:',
    default: 'my-project',
    validate: (v) => v.length > 0 || 'Name is required',
  });

  const template = await select({
    message: 'Choose a template:',
    choices: [
      { name: 'Minimal', value: 'minimal' },
      { name: 'Full-stack', value: 'fullstack' },
      { name: 'API only', value: 'api' },
    ],
  });

  const proceed = await confirm({
    message: `Create "${name}" with ${template} template?`,
    default: true,
  });

  if (!proceed) {
    console.log('Aborted.');
    process.exit(0);
  }
  return { name, template };
}

Always check process.stdout.isTTY before showing prompts. If the output is piped or running in CI, fall back to defaults or error with a clear message about which flags to pass.

4. Manage configuration files

Use cosmiconfig (Node.js) or similar to support multiple config formats.

import { cosmiconfig } from 'cosmiconfig';

const explorer = cosmiconfig('mytool', {
  searchPlaces: [
    'package.json',
    '.mytoolrc',
    '.mytoolrc.json',
    '.mytoolrc.yaml',
    'mytool.config.js',
    'mytool.config.ts',
  ],
});

async function loadConfig(flagOverrides: Record<string, unknown>) {
  const result = await explorer.search();
  const fileConfig = result?.config ?? {};

  // Merge: defaults < file config < env vars < flags
  return {
    output: 'dist',
    verbose: false,
    ...fileConfig,
    ...(process.env.MYTOOL_OUTPUT ? { output: process.env.MYTOOL_OUTPUT } : {}),
    ...flagOverrides,
  };
}

5. Write effective help text

Follow this template for every command's help output:

Usage: mytool deploy [options] <environment>

Deploy the application to a target environment.

Arguments:
  environment          target environment (staging, production)

Options:
  -d, --dry-run        show what would happen without deploying
  -t, --tag <tag>      docker image tag to deploy (default: "latest")
      --timeout <ms>   deploy timeout in milliseconds (default: "30000")
  -h, --help           display help for command

Examples:
  $ mytool deploy staging
  $ mytool deploy production --tag v2.1.0 --dry-run

Rules: show Usage: first with <required> and [optional] args. One-line description. Group options logically with --help and --version last. Always include 2-3 real examples at the bottom.

6. Handle stdin/stdout piping

Support stdin when no file argument is given. This makes the tool composable.

import { createReadStream } from 'fs';
import { stdin as processStdin } from 'process';

function getInputStream(filePath?: string): NodeJS.ReadableStream {
  if (filePath) return createReadStream(filePath);
  if (!process.stdin.isTTY) return processStdin;
  console.error('Error: No input. Provide a file or pipe stdin.');
  console.error('  mytool process <file>');
  console.error('  cat file.txt | mytool process');
  process.exit(2);
}

function output(data: unknown, json: boolean) {
  if (json) {
    process.stdout.write(JSON.stringify(data) + '\n');
  } else {
    console.log(formatHuman(data));
  }
}

7. Distribute the CLI

Node.js (npm) - set bin in package.json, ensure shebang #!/usr/bin/env node:

{
  "name": "mytool",
  "bin": { "mytool": "./dist/cli.js" },
  "files": ["dist"],
  "engines": { "node": ">=18" }
}

Python (pip) - use pyproject.toml entry points:

[project.scripts]
mytool = "mytool.cli:cli"

Go - go install github.com/org/mytool@latest. Cross-compile with GOOS=linux GOARCH=amd64 go build.

Rust - cargo install mytool. Cross-compile with cross. Distribute via crates.io or GitHub Releases.

8. Add shell completions

# Click: built-in completion support
# Users activate with:
# eval "$(_MYTOOL_COMPLETE=zsh_source mytool)"

// Clap: generate completions via clap_complete
use clap_complete::{generate, shells::Zsh};
generate(Zsh, &mut cli, "mytool", &mut std::io::stdout());

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Anti-patterns / common mistakes

| Mistake | Why it is wrong | What to do instead | |---|---|---| | Printing errors to stdout | Breaks piping - error text contaminates data stream | Use console.error() or sys.stderr.write() | | Exit code 0 on failure | Breaks && chaining and CI pipelines | Always process.exit(1) or sys.exit(1) on error | | Requiring interactivity | Breaks CI, cron jobs, and scripting | Accept all inputs as flags; prompt only when TTY + flag missing | | No --help on subcommands | Users cannot discover options | Every command and subcommand gets --help | | Inconsistent flag naming | --dry-run vs --dryRun vs --dry_run | Pick kebab-case for flags, be consistent everywhere | | Giant monolithic help text | Overwhelms users, hides important flags | Use subcommand groups; hide advanced flags in extended help | | Non-standard flag syntax | /flag or +flag or flag:value | Stick to POSIX: -f, --flag, --flag=value | | Swallowing errors silently | User has no idea something failed | Print error to stderr with context and suggested fix | | No --version flag | Users cannot report which version they run | Always add --version to the root command |

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Gotchas

1. Interactive prompts in CI/scripts - A confirm prompt that blocks waiting for user input will hang a CI job indefinitely with no error message. Always check process.stdin.isTTY (or equivalent) before prompting, and provide a --yes / -y flag that skips all confirmations.

2. Exit code 0 on partial failure - A command that processes 10 files but fails on 2 and still exits 0 breaks && chaining and CI pipelines silently. Track failures explicitly and exit non-zero when any operation failed, even if some succeeded.

3. Flag name inconsistency across subcommands - Having --dry-run on deploy but --dryRun on migrate creates a mental tax for users. Establish naming conventions (kebab-case) at project start and enforce them in every subcommand - inconsistency compounds with every new feature.

4. Node.js shebang missing or wrong - Distributing a Node CLI without #!/usr/bin/env node as the first line means users must run node mytool instead of mytool, and npm's bin linking won't work correctly. Always set the shebang and make the file executable (chmod +x).

5. Swallowing parser errors - Argument parsers like Commander.js call process.exit(1) on invalid args by default, but some configurations catch and suppress these errors. An invalid flag that silently falls back to defaults is extremely confusing. Ensure validation errors always produce a clear message to stderr and a non-zero exit code.

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References

For detailed patterns on specific CLI sub-domains, read the relevant file from the references/ folder:

• references/argument-parsing-patterns.md - advanced parsing patterns including variadic args, mutually exclusive flags, coercion, and validation across Node.js, Python, Go, and Rust
• references/config-file-patterns.md - config file formats, XDG Base Directory spec, schema validation, migration strategies, and environment variable conventions

Only load a references file if the current task requires it - they are long and will consume context.

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Companion check

On first activation of this skill in a conversation: check which companion skills are installed by running ls ~/.claude/skills/ ~/.agent/skills/ ~/.agents/skills/ .claude/skills/ .agent/skills/ .agents/skills/ 2>/dev/null. Compare the results against the recommended_skills field in this file's frontmatter. For any that are missing, mention them once and offer to install:

npx skills add AbsolutelySkilled/AbsolutelySkilled --skill <name>

Skip entirely if recommended_skills is empty or all companions are already installed.