Generate high-converting email subject lines and article headlines by combining David Ogilvy's advertising laws with copywriting frameworks. Focuses on attention, curiosity, specific benefits, and the "80 cents" rule.
"On the average, five times as many people read the headline as read the body copy. When you have written your headline, you have spent eighty cents out of your dollar." — David Ogilvy
This skill blends David Ogilvy's research-backed advertising principles with Emma Stratton's "Make It Punchy" methodology. It stops the scroll and earns the click by treating the headline as the most valuable asset of your writing.
Use this skill when asked to:
If your headline fails, your content is invisible. Ogilvy often wrote 20+ headlines for a single ad. Never settle for the first draft.
Implication: Spend 80% of your effort on the headline. Generate at least 5-10 options before selecting the best.
Don't write for everyone. Flag down your specific reader. Ogilvy said: "Use the headline to flag the specific prospect."
| Too Broad | Flagged | |-----------|---------| | "How to manage finances." | "Advice for Startups dealing with Cash Burn." | | "Tips for better meetings." | "For Engineering Managers who hate status meetings." | | "Improve your health." | "To Parents Over 40 who want more energy." |
Would you actually say this subject line to a friend at a BBQ?
| Fail | Pass | |------|------| | "Maximizing Synergies for Q3." | "How to get your team to work faster this quarter." | | "Operational Excellence Framework" | "Stop wasting time on meetings that go nowhere." | | "Leveraging AI for Growth" | "How AI can help you close deals faster." |
Every headline must perform at least one of these functions:
The best headlines do multiple functions at once.
Use these as starting points, then refine using the BBQ test.
Why it works: Pure utility. Ogilvy found "How to" headlines among the highest performing because they promise a specific solution.
Structure: How to [Benefit] without [Pain].
| Type | Example | |------|---------| | Ogilvy Style | "How to Create Advertising That Sells" | | Punchy Style | "How to get your nights and weekends back" | | B2B Example | "How to close enterprise deals without discounting" |
Why it works: Consumers are always looking for what is new. Use power words like New, Announcing, Finally, Now, At Last.
Structure: [News Word]: [The Big Change/Benefit].
| Type | Example | |------|---------| | Ogilvy Style | "Announcing: The new Rolls-Royce..." | | Punchy Style | "Finally: a way to track expenses that isn't boring." | | B2B Example | "Now: One dashboard for your entire security stack." |
Why it works: It calls out the specific "A+ Customer" and ignores everyone else.
Structure: [Audience Call Out]: [Big Promise].
| Type | Example | |------|---------| | Ogilvy Style | "To men who want to quit work someday." | | Punchy Style | "For Engineering Managers who hate status meetings." | | B2B Example | "To CTOs tired of managing legacy infrastructure." |
Why it works: It creates an itch the reader must scratch. Caution: Do not use if the content doesn't deliver.
Structure: The [Number/Adjective] secret to [Desire].
| Type | Example | |------|---------| | Ogilvy Style | "The man in the Hathaway shirt." (Visual curiosity) | | Punchy Style | "The one thing killing your team's velocity (it's not code quality)." | | B2B Example | "The 3-minute trick our top performers use every morning." |
Why it works: Direct and authoritative. Tells the user exactly what to do.
Structure: Stop [Pain]. Start [Benefit].
| Type | Example | |------|---------| | Ogilvy Style | "Give her a Arpege." | | Punchy Style | "Stop drowning in tickets. Start automating support." | | B2B Example | "Stop guessing. Start knowing where every deal stands." |
Email subject lines face harder constraints than print headlines.
Most people check email on phones. If your "punch" is at the end, it gets cut off.
| Bad (punch lost) | Good (front-loaded) | |------------------|---------------------| | "We are engaging in a new partnership that will help you save money." | "Save money: Our new partnership." | | "Following up on our conversation from last week about the proposal" | "Re: the proposal - quick question" | | "I wanted to share some exciting news about our platform updates" | "New: 3 features you asked for" |
Ogilvy loved long headlines. In email, use the Subject Line as the hook and the Preview Text as the explanation.
| Subject Line | Preview Text | |--------------|--------------| | 5 ways to fix your SEO | Number 3 is the mistake most SaaS founders make... | | Quick question about [Company] | Not selling anything, just curious about your approach to... | | re: your LinkedIn post | The one about X - had a follow-up thought... |
| Generic | Personalized | |---------|--------------| | "Improve your sales process" | "[Name], noticed your team just expanded" | | "New features available" | "For [Company]: the integration you requested" | | "Let's connect" | "[Mutual connection] suggested we talk" |
Run every headline through this gauntlet before publishing:
Sprinkle (but don't stuff) these into your headlines.
| Category | Words | |----------|-------| | News | New, Now, Announcing, Introducing, Finally, At Last, Suddenly | | Utility | How to, Why, Which, This, Advice, Facts | | Urgency | Hurry, Last Chance, Only, Today, Limited | | Benefit | Save, Easy, Quick, Guaranteed, Proven, Results, Free | | Emotion | Darling, Love, Fear, Proud, Wanted, Secret | | Logic | Because, Consequently, Therefore, Due to |
| Instead of... | Try... | |---------------|--------| | Leverage | Use | | Synergy | Working together | | Optimize | Improve, Boost | | Transform | Change, Fix | | Revolutionize | A better way to... | | Enable | Help, Let | | Utilize | Use | | Facilitate | Make easier | | End-to-end | Complete, Full |
| Version | Headline | |---------|----------| | Boring | "Update on our software features for Q3." | | Punchy (Stratton) | "Get your books done faster this quarter." | | Ogilvy Optimized | "For Accountants who want to leave the office by 5 PM." |
| Version | Headline | |---------|----------| | Boring | "Tips for lifting weights properly." | | Punchy (Stratton) | "Stop hurting your back when you deadlift." | | Ogilvy Optimized | "How to deadlift without back pain (3 proven tips)." |
| Version | Headline | |---------|----------| | Boring | "Mandatory HR Training Reminder." | | Punchy (Stratton) | "Please finish your training by Friday!" | | Ogilvy Optimized | "Warning: 3 days left to complete training." |
| Version | Subject Line | |---------|--------------| | Boring | "Introduction to our services" | | Punchy (Stratton) | "Quick idea for [Company]" | | Ogilvy Optimized | "For [Name]: The one thing slowing your deals" |
| Version | Subject Line | |---------|--------------| | Boring | "Following up on my previous email" | | Punchy (Stratton) | "Bumping this up" | | Ogilvy Optimized | "Re: [Original topic] - found something relevant" |
When generating headlines, deliver:
CONTEXT: [Brief description of what the headline is for]
AUDIENCE: [Who this is flagging]
HEADLINE OPTIONS (ranked by recommendation):
1. [Best option] — [Why this works]
2. [Second option] — [Why this works]
3. [Third option] — [Why this works]
4. [Fourth option] — [Alternative angle]
5. [Fifth option] — [Alternative angle]
RECOMMENDED: #[Number] because [brief rationale]
SUBJECT LINE: [The headline]
PREVIEW TEXT: [The supporting text that appears after]
CHARACTER COUNT: [Number]
Generate 10 options using varied formulas:
Before writing, clarify:
Never settle for the first headline. Generate at least 5-10 variations using different formulas.
Run top candidates through the Ogilvy x Punchy checklist.
Ask: "Can I make this MORE specific?" Replace vague benefits with concrete numbers, outcomes, or timeframes.
Does it sound like something a human would say? If it sounds like corporate-speak, rewrite.
For deeper context on the principles behind this skill:
| Reference | Content |
|-----------|---------|
| references/01-headline-rules-ogilvy.md | The "80 cents" rule, four functions of a headline, technical parameters, what to avoid |
| references/02-body-copy-rules-ogilvy.md | Long copy principles, "Reason Why" technique, structural techniques, typography rules |
| references/03-big-idea-framework-ogilvy.md | The Big Idea checklist, brand image, USP, Big Idea vs. Gimmick |
| references/04-research-methodology-ogilvy.md | Gallup training influence, testing promises, competitor analysis, research process |
| references/05-power-words-ogilvy.md | Power words by category, words to avoid, quotation mark effect, combining power words |
| Reference | Content |
|-----------|---------|
| references/Unlocking Ogilvy's Copywriting Genius.md | Full synthesis of Ogilvy's methodology from "Confessions of an Advertising Man" |
| references/ogilvy.md | Historical Ogilvy campaign examples (Guinness, Dove, Hathaway, etc.) |
This skill works as part of a larger workflow:
The headline is always first. It's 80 cents of your dollar.
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Category:media-generate