18 Tips For Writing Engaging Headlines and 27 Makeovers That Saved Stories From Extinction

    by Kurt Gessler
    November 30, 2016

    This article was originally published on Medium.

    Let’s start with the obvious: Most news sites are in a headline crisis.

    You must have a certain sense of desperation in writing web headlines, like those eight words are the difference between that column’s or blog’s life or death.

    It’s truly a crisis because your headline is the first — and maybe the best —  shot you have at attracting a reader.


    Yet many headlines look like the ones above.

    Honestly, based on those examples, it’s hard to argue against Will Oremus’ case in Slate that “local media routinely fails to emphasize the most interesting aspect of amazing news stories.”

    “(Media organizations are) laboring under the mistaken assumption that the role of a headline is to summarize a few relevant facts from a story that people will read regardless. That assumption is a relic of a time when people’s choice of news sources was constrained by the few newspapers or magazines they happened to subscribe to, or the few channels available in their basic cable package. Even then, I’m certain that fascinating stories went unread thanks to dreary headlines. Editors just didn’t have the analytics tools to measure it.”


    And newspaper websites seem to be the epicenter of this epidemic. Now, there are several understandable reasons behind this. First, being understated is baked into the newspaper workflow because you can rely on the full context of a printed page. In a newspaper, a story might get a subhead, pullquote, graphic and photo. Online, you don’t get that sumptuous setting. Offsite, the source may be harder to discern, which in many cases suggests geographic (Boston Globe, Houston Chronicle) or topical context. And looking at just a headline and link in an RSS feed won’t tell you what section, giving readers a clue that “Brady” in the headline means Tom not Jim or Bunch.

    Online, your product is unbundled. You get 10 words. Or 8. Or maybe 13, like I used above, to market your work. Digital success is like selling a newspaper story by story rather than day by day or week by week. And in selling that day’s paper, by subscription or newsstand, there’s just less urgency to make the headline awesome on that 150-word story buried at the bottom of page 11. Sections and geographic centers all are comfortable assumptions you can’t make in digital headlines. You must have a certain sense of desperation in writing web headlines, like those eight words are the difference between that column’s or blog’s life or death. Mostly, because it is. You aren’t owed readership. Your headline helps earn it — along with a handful of other factors like author and brand.

    So any strategy involving growing and sustaining digital audience must incorporate excellence in headline writing. Must.

    A few points to clarify here as we begin. I’ll be discussing writing for readers here, not for search engine optimization. That will be a consideration at times, but mostly we’re talking about people creating headlines for people.

    The primary metric we’ll use is homepage click-through rate — the rate in which people loyal to the brand select (or don’t) a piece of content from a field of competing stories. I’m not going to focus on social analytics, engaged time, quality clicks etc. Those can be strongly influenced by platform, design or story length. Engagement time is the job of the content and the UX. The headline just gets people there. That’s our mission here.

    And lastly, I’m not trying to sell anything. There are many great tools to leverage realtime metrics and A/B test headlines, like Chartbeat, Taboola and Optimizely. But all of those are still based on crafting good headlines. You don’t learn much A/B testing garbage.

    So we’ll start with the 18 tips on writing effective headlines to help you create those engaging options. Then we’ll go through 27 examples of stories on ChicagoTribune.com that were first published with vague or print-centric headlines. I’ve picked these 27 examples because, in all those cases, we at least doubled realtime homepage engagement (click-through rate) after we made the change. We based this on Chartbeat’s heads-up display. So if 20 people were clicking on a headline before we reworked it, at least 40 were after. Most exceeded that threshold. These 27 cases were game-changers not just a nominal improvement. Hopefully, between the tips and practical lessons in the before-and-after examples, there are a few takeaways.

    18 great headline-writing tips

    1. Be clear and focused, first and foremost. Directly tell the reader why they should care or how this affects his or her life. There is nothing more important than clarity. Nothing. Straight headlines aren’t dull — they are lean and effective, elegant in their own right.

    Part of being clear, at times, is stating what the writer and editor believe to be obvious. “Homeowners face tax hike under mayor’s budget plan” makes sense if your readers come from a single town. But how likely is that? “Chicago homeowners face tax hike under Mayor Emanuel’s budget plan” is not only more clear, but also better for SEO. And considering nearly of third of Americans couldn’t name the vice president, don’t assume they know their mayor or wouldn’t benefit from knowing exactly what city we’re talking about.

    2. Don’t get too cute or punny. Let me underscore that: Most pun headlines suck. Why? You assume the reader gets the joke. You assume there are no language barriers. You assume originality, that your pun hasn’t been used dozens of times already. And worst, you assume there’s nothing more interesting in the story.

    Here’s a few examples of pun headlines where the joke is the focus rather than the story. And when your story centers around child molestation, like the Hastert piece, an attempt at clever wordplay only trivializes a serious matter.







    What does an officer being “bullish” have to do with an arrest? And Pleez, sadly, has already closed. I blame the imperceptible headline.

    3. Write it so it reads fast. The first few words are critical; don’t make a reader hunt to find key points. Front-load them into your headline. This also helps with SEO.

    “Billy Bush, embroiled in Trump tape scandal, is suspended from ‘Today’ show” — Los Angeles Times.

    “Florence Henderson, TV’s Carol Brady, dies at 82” — CNN.

    Don’t start with “‘Brady Bunch’ star” or “TV’s Carol Brady.” Start with the name of the recognizable actress or disgraced celebrity.

    For the same reasons, unless it’s absolutely critical, don’t start a headline with the attribution. “Police confirm serial killer escaped from jail” is less effective than “Serial killer escaped from jail, police confirm.” Key details come first.

    4. If the deadline isn’t now, write multiple headlines.

    Challenge yourself. Upworthy espouses 25 discrete headlines per story. That feels excessive, but it does suggest you shouldn’t stop after your first headline. I find writing at least three to be extremely helpful.

    5. Write with an active voice.

    6. Favor proper nouns (names, teams, locations). This also helps with SEO. But also realize that sometimes being vague may be beneficial. Is the incident more important than the locale? Is the law more important than who proposed it? Both approaches have their place. Know when to use them.

    7. Is the writer important? Consider including her or him.

    8. Headlines with eight words or more perform best, says Outbrain. Now here you may be at odds with SEO best practices. We’ve also seen SEO benefit to keeping headlines generally between 40 characters and 77 characters. And Moz recommends headlines of around 60 characters to avoid truncation in search results pages. Others say 70 characters. The answer, in my mind, is to just write your best headline being mindful of where readers may not see the rest. A great headline that goes a little long is better than an SEO perfect headline that’s revolting.

    9. Ask a critical question in your headline.

    10. Use descriptive and evocative words, terms that inspire or amuse or anger. A University of Pennsylvania study suggests eliciting an emotional response is the critical reason content goes viral. Chose words with power.

    11. Pique a reader’s curiosity — but don’t be click-baity. Again, clarity first. You erode brand trust and confidence if you’re just teasing and never delivering. Don’t play the guess-what-band-is-coming-to-town game. Be a compelling and reliable source of information.

    12. How-to’s, lists and tips can make compelling number-based headlines (“8 headline mistakes you can avoid” or “How you can avoid these 8 headline mistakes”). But the content must support the headline. You can’t use this list-style of headline on a narrative story. Headline and story must be in concert not conflict.

    13. Have a great quote? Use it. If you’re stuck, this is usually the shortest path to a unique headline.

    14. Don’t limit yourself to the story’s lede (beginning). The headline has to promote the most-engaging element, whether that’s a number, quote, fact, thought, topic, opinion etc. Maybe that’s 10 paragraphs in.

    15. Only use the most common acronyms. FBI? Sure. SA’s office? Probably not. However, you should use abbreviations like “feds.” Headlines should be approachable and conversational.

    16. Some words just suck. Don’t use those. Here’s a few weak headline words I hate. All of them are hard to read, weak, vague or jargony. Post more in the comments and I’ll add them.

    Figure, as a noun for an individual
    Issue, as a noun
    Flap, as a noun
    Fans, as a verb
    Announce (this is almost always extraneous)
    Appropriate (verb)

    17. Focus on impact and implications. Why is this story important to people? I like a quote from co-worker Mark Jacob, metro editor at the Chicago Tribune: “Tell people why the story is about them.”

    Structures like the ones below are becoming a little threadbare, but at their core they aim to be direct and useful, albeit with a touch of drama.

    Here’s the truth about XXX
    This is what XXX means to you
    Experts offer advice on XXX
    XXX things you need to know about YYY
    This is the true story of XXX
    XXX is a problem. This is the solution
    XXX happened. Then YYY did.

    She called the man who sexually assaulted her a rapist. Then he sued her for defamation. — Washington Post

    Looks like the 2nd debate had about 20% fewer viewers than the 1st. Here are the reasons why. — CNN

    Hard to argue those aren’t compelling reads.

    18. But the most important tip isn’t arcane or gimmicky. It’s obvious, but it’s often ignored. Make absolutely sure the most interesting, most important part of the story is conveyed in your headline. And that usually takes time and effort. There’s no way to write a great headline by just skimming the story.

    This project with amazing visuals went live on the Tribune with this headline: “Returning to the prairie.”


    It doesn’t get much more vague than that. I knew it would do poorly, and in fact Chartbeat showed that it was being ignored by most of our readers. Realtime audience metrics helps a lot to identify weak headlines. So right away I knew it needed an intervention. It took me 10+ minutes, but I settled on “Man sold home, spent last decade to create 60-acre prairie garden.” And I played up the geography, Chicago’s affluent North Shore, in the readout. I probably should have put North Shore in the headline anyway.


    A sense of scale. Hint of commitment through time. Clarity. The change had immediate impact and became the second-most read story of the day.

    I didn’t change a photo or re-write the piece. I simply adjusted how it was being marketed to the audience. That’s the power of the headline.

    Here’s 26 more before-and-after examples, all with lessons based on those tips.

    Headline makeovers that doubled homepage click-throughs





    Removed jargon. Chose geography over specificity of a single restaurant.





    Replaced vague “think twice” with specifics of why you should care.





    Added powerful narrative of the crime and its geography.





    Replaced vague “multiple tools” with exotic specifics. The story is about those details.




    Replaced vague “exultant” with examples. People we’re just happy, they wee crying.





    Removed geography and focused on nature of crime and relationship of subjects.





    Removed jargon like “Big Coal” and focused on consumer angle. Clarified geography as Illinois.




    The nature of recipe is far more compelling than “limited edition” implies.




    Added clarity and details. I mean, millions of things are made from scratch in Chicago.




    Tried to add scale and intrigue by replacing vague phrase “old-school effort.” In retrospect, even this could be better, focusing on the technical challenges.




    Added cost, narrowed geography and used a powerful quote.





    Used quote and more evocative language.





    Narrowed geography to not needlessly scare parents of other Chicago schools.





    Added scale and removed odd phrase “lobster roll addiction.” That’s not a thing.





    Added crime, victim and geography. The “gift to mom” was the arrests in her son’s murder, which isn’t very clear.





    Added humor and a little specificity since “complicated” is soft.





    Focused on a unique element of story.





    Removed pun and focused on consumer novelty of the suit.





    Added specificity and scope.





    Added key institution, purpose and profile of the effort.





    Opted to remove names lesser-known athletes (vague can be good) and focused on the nature of the allegations.





    First headline was clear and solid. However, it lacked the highest-level implication.





    Pulled out attention-grabbing quote as focus. Probably could have kept “Chicago.”





    Removed “cha-ching” phrase and focused clearly on the consumer aspect.





    Initial headline lacked clarity and detail.





    Spelled out what vague phrase “difficult questions” meant.

    Now, if your site publishes 12 articles and columns, it’s probably easy to apply these standards to all your content. However, in many cases it’s simply not feasible to A/B test 200 headlines a day. One viable game plan would be to focus on key stories, those on a home page or at the top of the app. Or focus on the stories that are most important to your mission. You also could look at realtime metrics to see what’s under performing at large. Another process we at the Chicago Tribune took was to analyze what types of content our readers most valued, so that when a story from a traditionally popular area was under performing, we tried a new headline rather than assume the story was the problem.

    And, of course, sometimes you only have to look at a headline like “Cheater, cheater” or “Putting Chicago’s violence on the table” to determine a course correction is needed. And once you rescue those stories from bad headlines, hey, feel free to be a little “braggadocious.”

    H/T to Jim Jaworski, Tom Palmer and Joe Ruppel for some of the examples.


    Kurt Gessler is the deputy editor for digital news at the Chicago Tribune. He also teaches at The Medill School of Journalism, Media, Integrated Marketing Communications at Northwestern University.

    Tagged: avoid these words chicago tribune headline writing online headlines

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