Newsletter Creation & Curation Skill

PLAYBOOK.md

Mode

quick

standard

deep

standard

quick

deep

Context Loading Gates

• Company context: What product/service? Who is the ICP?
• Newsletter goal: Lead gen / thought leadership / personal brand / category ownership
• Industry vertical: Sales Tech / HR Tech / Fintech / Operations Tech
• Company stage: Series A / Series B / Series C+
• Role: Founder / VP-Director / PMM-Content / Enterprise employee
• Geography: US-first / India-first
• Prior issues: Any existing issues to maintain consistency and voice?
• Approval constraints: Does this need legal/brand/manager review?

Goal: [lead_gen | thought_leadership | personal_brand | category_ownership]
Industry: [sales_tech | hr_tech | fintech | ops_tech]
Stage: [series_a | series_b | series_c_plus]
Role: [founder | vp_director | pmm_content | enterprise_employee]
Geography: [us_first | india_first]

Phase 1: Context Analysis

1. Template match: Which industry template best fits? (Sales Tech = data-heavy; HR Tech = research-led; Fintech = compliance-aware; Ops Tech = practical)
2. Cadence match: Series A = weekly/bi-weekly for simplicity; Series B = weekly with process; Series C+ = media-grade weekly with pillars
3. Role constraints: Founder = direct POV allowed; Employee = approval checkpoint required before final draft
4. Geography adjustments: India-first = IST timing + local examples; US-first = EST/PST + US benchmarks
5. Goal-content alignment: Lead gen needs a clear conversion CTA; thought leadership needs original insight, not general content

For [ICP], we publish [cadence] to achieve [goal] with [format].

Phase 2: Issue Blueprint

## Issue Blueprint

**Strategy:** For [ICP], [cadence] to achieve [goal].
**Industry tone:** [tactical/research-led/compliance-aware/practical]
**Approval required:** [yes/no — who]

**Sections:**
1. Subject lines (3 options) — [~words each]
2. Hook — [target ~75 words]
3. Core insight — [target ~200 words]
4. Actionable playbook — [target ~150 words, 3-5 steps]
5. CTA — [1 sentence, singular action]

Phase 3: Full Issue Draft

Subject Line Options (3 required)

• A: Curiosity/open loop ("The metric most [ICP] ignore")
• B: Specific + benefit ("How [Company type] achieves [X] in [timeframe]")
• C: Contrarian/bold ("Stop [common behavior]. Do this instead.")

Hook

• First 2 sentences must earn the read
• Lead with the problem + stakes
• Target: busy reader can extract the point in 60 seconds

Core Insight

• One primary takeaway per issue — not three
• Support with: data, framework, or named pattern
• Include specific numbers or named examples wherever possible

Actionable Playbook

• 3-5 steps or checklist items
• Each step must be implementable, not just conceptual
• Series A = simpler steps; Series C+ = more sophisticated process

CTA

• ONE measurable action only
• Options: reply with [X], click [link], share [asset], book [demo]
• Never use vague CTAs ("Learn more")

Phase 4: Refinement Checklist

• Clarity

  : Can a busy reader extract value in 60 seconds?

• Specificity

  : Does each section include concrete guidance or evidence?

• Relevance

  : Does tone match industry and role constraints?

• Compliance

  : For fintech/employee-led, is a legal/manager review step included?

• Consistency

  : Does voice align with prior issues (if any were provided)?

• CTA

  : Is there exactly ONE measurable CTA — not two, not zero?

Phase 5: Self-Critique Pass (REQUIRED)

• Does the subject line A option create genuine curiosity without being clickbait?
• Does the hook deliver a problem + stakes in the first 2 sentences?
• Is the core insight something subscribers couldn't get from a generic AI prompt?
• Does the playbook have steps that are specific to this audience, not generic "tips"?
• Is the CTA actually measurable — i.e., can they track whether it worked?
• For fintech/employee contexts: is there an explicit approval checkpoint?

Iteration Protocol

1. Ask: "Does the hook earn the read? Does the playbook feel actionable for your audience?"
2. If hook is weak → rewrite using a different angle (data-led, story-led, or contrarian)
3. If playbook is too generic → ask for a specific example from their own experience to ground it
4. For next issue: "Want me to save these content themes so the next issue builds on this one?"

Output Structure

## Newsletter Issue: [Name] — Issue #[X] — [Date]
**Strategy:** For [ICP], [cadence] to achieve [goal].

---

### Subject Line Options
A) [Curiosity/open loop]
B) [Specific + benefit]  
C) [Contrarian/bold]
**Recommended:** [A/B/C] — [reason]

---

### Hook
[2-3 sentences — problem + stakes]

---

### Core Insight
[200-300 words — data, framework, or named pattern]

---

### Actionable Playbook
1. [Step]
2. [Step]
3. [Step]

---

### CTA
[Single measurable action]

---

### Distribution Plan
- **Send time:** [Day, Time, Timezone]
- **LinkedIn amplification:** [Post angle / hook]
- **Secondary channel:** [Platform + angle]

### KPI Targets
- Open rate goal: [%]
- CTR goal: [%]
- Primary metric: [SQLs / subscribers / replies]

### Approval Required
[Yes — [who] | No]

### Self-Critique Notes
[Issues flagged + revisions made]

Playbook Map (Deep Dives in

PLAYBOOK.md

)

• Sales Tech strategy:

  SECTION A

• HR Tech strategy:

  SECTION B

• Fintech strategy:

  SECTION C

• Operations Tech strategy:

  SECTION D

• Role approvals and geography tactics:

  CROSS-CUTTING: UNIVERSAL FRAMEWORKS