Plan Newsletter Issue

Overview

This skill takes a topic and produces a complete newsletter issue plan with draft content, subject line options, opening hook options, and social promotion posts. It is a thin orchestrator — every content generation step delegates to a foundation skill. This skill contains workflow sequence and platform-specific decisions only, not implementation logic.

When to Use

Use this skill when:

• Planning a new newsletter issue from a topic or idea
• Repurposing existing content (video transcript, notes, research) into a newsletter
• Creating a content plan for Substack or another newsletter platform

Prerequisites

A topic or source material is required. This can be:

• A topic idea or keyword
• A video transcript to repurpose
• Existing notes or research
• A URL or document to build from

If research already exists or the user is repurposing existing content, the research step can be skipped.

Planning Workflow

Execute all steps below sequentially. Add these as ToDos to track progress.

Step 1: Research the Topic

Invoke content-strategy:research to understand the content landscape and identify the best angle for the newsletter issue.

• Pass the topic, audience context, and any source material to the research skill.
• The research skill will analyze competitors, identify gaps, and produce actionable insights.

Skip condition: Skip this step if the user provides existing research, or if working from existing content (e.g., repurposing a video transcript). Note the reason for skipping in the plan.

Step 2: Draft the Newsletter Issue

Invoke writing:copywriting to draft the full newsletter issue.

• The copywriting skill will automatically load references/newsletter.md for newsletter structure and conventions.
• The copywriting skill will automatically invoke writing:voice for voice consistency.
• Pass the research findings (or source material) and topic context.
• The draft should follow the newsletter reference structure including sections, formatting, and CTAs.

Step 3: Generate Subject Line Options

Invoke content-strategy:title to generate 3-5 subject line options.

• The title skill will automatically load references/newsletter-subject-lines.md for subject line patterns.
• Each option must include:
  • Subject line text
  • Preview text (the snippet shown in email clients)
  • Rationale for why it will perform well
  • Star rating (1-3 stars) indicating recommendation strength

Step 4: Generate Opening Hook Options

Invoke content-strategy:hook to generate 2-3 opening paragraph options.

• The hook skill will automatically load references/newsletter-hooks.md for opening patterns.
• Each option must include:
  • Full opening paragraph text
  • Hook strategy description
  • Rationale and alignment with the selected subject line
  • Star rating (1-3 stars) indicating recommendation strength

Step 5: Generate Social Promotion Posts

Invoke writing:copywriting separately for each platform:

1. Twitter/X thread — the copywriting skill loads references/twitter.md for thread structure and character limits.
2. LinkedIn post — the copywriting skill loads references/linkedin.md for post conventions.
3. Substack Note — the copywriting skill loads references/substack-notes.md for note formatting.

Each promotion post should tease the newsletter content and drive subscriptions/reads.

Step 6: Generate Header Image (Optional)

Invoke visual-design:social-graphic to generate a newsletter header image.

• Only invoke if the user requests a header image or if the newsletter platform benefits from one.
• If not requested, mark as “Not requested” in the plan.

Step 7: Present Complete Plan

Present the full plan to the user for review. Include all options with star ratings so the user can make informed selections.

Output Structure

Save the plan to ./newsletter/issues/[issue_name]/plan.md. Create the directory if it doesn’t exist. Use a slugified version of the topic as the issue name (e.g., ai-coding-assistants).

The plan file must follow this structure:

# Newsletter Issue Plan: [Topic]

## Research Summary
[Key findings and angle — or "Based on [source material]" if repurposing]

## Subject Lines
[3-5 options with preview text, rationale, and star ratings]

## Opening Hook Options
[2-3 opening paragraphs with strategy, rationale, and star ratings]

## Draft Issue
[Full newsletter draft following newsletter.md structure]

## Social Promotion
### Twitter/X Thread
[Thread draft]
### LinkedIn Post
[Post draft]
### Substack Note
[Note draft]

## Header Image
[Generated image or "Not requested"]

Execution Guidelines

Always Invoke Foundation Skills

NEVER generate content manually. Always delegate to the appropriate skill:

• content-strategy:research for research
• writing:copywriting for all written content (newsletter draft and social posts)
• content-strategy:title for subject lines
• content-strategy:hook for opening hooks
• visual-design:social-graphic for header images

Provide Multiple Options

CRITICAL: Present all options with star ratings so the user can choose. Do not select a single option on the user’s behalf.

Back Recommendations with Research

When rating options with stars:

• Reference research findings or source material insights
• Explain why a particular angle or framing will resonate
• Note how the option addresses identified content gaps

Quality Checklist

Verify completion before presenting the plan:

• Research conducted (or source material loaded)
• content-strategy:research invoked (or skipped with reason)
• writing:copywriting invoked for newsletter draft
• content-strategy:title invoked for subject lines
• content-strategy:hook invoked for opening hooks
• writing:copywriting invoked for social promotion posts
• All written content goes through writing:voice (handled by copywriting skill)
• Complete plan presented to user

Common Pitfalls to Avoid

1. Writing content directly: Drafting newsletter text or social posts without invoking the copywriting skill. Always delegate.
2. Skipping research without reason: If research is skipped, document why (e.g., “Repurposing video transcript provided by user”).
3. Single option only: Presenting one subject line or one hook. Always provide multiple options with ratings.
4. Missing social promotion: Forgetting one of the three platforms (Twitter/X, LinkedIn, Substack Notes).
5. No voice consistency: The copywriting skill handles this automatically via writing:voice, but verify the output reads consistently.

Example Execution

Scenario: User asks to plan a newsletter about “Building AI agents with memory”

1. Research: Invoke content-strategy:research with topic “AI agents with memory” to identify content gaps and angles.
2. Draft: Invoke writing:copywriting with research findings to produce the full newsletter draft.
3. Subject lines: Invoke content-strategy:title to generate 4 subject line options with preview text.
4. Opening hooks: Invoke content-strategy:hook to generate 3 opening paragraph options.
5. Social posts: Invoke writing:copywriting three times for Twitter/X thread, LinkedIn post, and Substack Note.
6. Header image: User did not request one — mark “Not requested.”
7. Present plan: Save to ./newsletter/issues/ai-agents-with-memory/plan.md and present to user.

Result: Complete newsletter issue plan with multiple options at each decision point, all backed by research insights and generated through specialized foundation skills.