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How to write headlines that make people want to read your content

How to write a headline content strategy
Back in the day before social media marketing was even a thing we were writing "clickbait" headlines. Our display ads only lasted a day and we did it all again the next day. We were the first original SEO company that didn't require a Google search to find out what was ranking for the day.

How to write headlines that make people want to read your content

Back in the day before social media marketing was even a thing we were writing “clickbait” headlines. Our display ads only lasted a day and we did it all again the next day. We were the first original SEO company that didn’t require a Google search to find out what was ranking for the day.

I used to sit in the hot seat of a daily newspaper that had over 5,500,000 readers and hit 680,000 daily sales at its peak. Our job was to intrigue readers to buy the day’s newspaper by writing mini billboards that we used to put up on street poles.

It was our on-the-pole marketing tactics that were the first teaser for people to invest their pocket change for a companion before the workday started.

We used to print thousands of these little teasers all around the country and these were all thought up at the end of our editorial meetings. We would pick the lead stories from the different news editors and decide which stories deserved an A3 size billboard.

It used to be a feeding frenzy of creativity as 30 plus of some of the most talented writers, journalists, and editors let loose their most bizarre, loud, outrageous, genius, and anything in-between teasers of six words or less.

Above: Some of the outrageously fun billboards that we came up with.


We had the pride of knowing that during the lunch breaks when five and half million people sat down to talk to their fellow colleagues that our stories would be on the lips of those that had been intrigued enough to invest in our day’s offering.

Our main marketing plan, at its core, was to steal the attention of a potential reader, take them for a ride in under 2 seconds and spit them out the other side and leave them burning hot to read the story.

The clients, advertisers and directors loved us and cheered us on as we continued to move the needle higher and higher.

Sexy SEO services strategy shouldn’t suck

But, it came with the caveat that had some serious consequences of – Don’t throw out a line that is so sexy that when the person picked up the newspaper that they would feel that the fire that was put there in the first place would be met with an ice cold jug of “you lied to us”. We had to write content that had the same level as our less than six words temptress….and we did. It was glorious!

Then everything changed and we were hit with this wonderful new storytelling medium that was powered by instant gratification and instant betrayal if you got it wrong. The digital age of websites and Google were stealing our billboard SEO services by offering instantaneous gratification from the palm of your hand.

We had shareholders and hungry advertising departments that wanted their slick digital fingerprints flashing all over beautiful products or services that teams of us had worked so hard to make it amazing.

We left it to the young and inexperienced, in life, to lead us through the mecca of digital marketing and the finer points of web marketing and we learned our lessons quickly.

We learned that our punchy knock-out billboard-style words worked extremely well for search engine optimisation and we were leading the pack when it came to having eyeballs moving onto our digital content.

We became the rock-stars of the Naspers Group and I have fond memories of explaining to Directors and board members how the rock-and-roll studs of yesteryear were once again headlining in another medium. It was glorious!

The lessons of media marketing attention

There were a couple of interesting lessons that came with this amazing new world. Firstly, our marketing budget was being moved away from our beautifully crafted A3 billboards and to our online marketing realm where hundreds of thousands more people could see your clever little digital billboards in less time that it took to go and collect the proofs from the big A3 printer.

Secondly, budgets changed and companies started to realise that they didn’t have to roll the dice with knowing whether their print media was working or not. They had an instant marketing research tool that would tell them exactly if their shiny digital advert had been successful.

Clients were consuming information differently and the newsroom started to see people shift with one foot in the slowing print medium and the other trying to desperately keep up with the pace of this new giant of a machine where anyone, regardless of their background, rank, or especially intelligence could capture people’s attention.

Times were tough and there was much worry, but there was also a huge growing excitement.

Feeding the digital marketing machine

This thing called Facebook was launching and it bought along with it all kinds of new social media marketing strategies that you had the chance to write something and dangle it directly in front of your audience. We developed a marketing plan template that involved putting up a few of our billboard-style headlines that teased some of our best content which coaxed potential readers to move into our digital space.

It was great and our marketing strategy was working well and we were thriving in this new digital age.

We learnt from many thousands of teasers which ones worked and which ones our audience would respond to. We started expanding into a digital space where we were writing Google ads and targeting b2b companies with more corporate slanting social media content. Our b2b customers increased and we started focusing on b2b marketing strategies to get the fuel to run our big newsroom digital machine.

The b2b buyer was very different to the readers and we had to completely change the way that we spoke. Our SEO strategy was to move away from the traditional straight-out call to action but to try and get them to see the headspace of the clients that we were working with every day.

Above: One of the corporate facing campaigns, featuring adsman, your daily companion.

Putting it all together

A lot of media agencies were falling short because they were promising a good time in their sexy display ads and their drawn-out stories that seemed to take the long way home past shiny meaningless billboards that just turned you off of what you were reading.

We were flying high and we were creating content marketing with multi-channel touchpoints that kept clients, advertisers, the board, and more importantly the people in our newsroom content and happy.

A lot has changed since those days, but a lot remains at the core of what we do. Those lessons that were burnt into my soul raise their head every day and provide me with endless joy and fulfillment as I chase that high of writing that perfect headline that converts .

Here are 7 rules that I live by when writing headlines for content, adverts, or anything that needs a bit of flavour.



1. If you tease it, your content needs to follow-through

If your content doesn’t follow through and promise what it’s supposed to then you have broken the trust then you will struggle to grab their attention back again. Make sure that your headline fits your content and is on-brand.



2. You can’t shout about the unknown

There’s a reason why we always wrote the billboards at the end of the meetings, so make sure to write your content first and then tackle your headline.



3. Need some help writing a headline? Stuck?

• Think about who you’re writing for and if they are sophisticated, playful or eccentric? 
• Use your main point, product, or service in the headline. 
• Highlight one of the problems or solutions that you’re solving or combine both. 
• Try to appeal to the emotions of the audience you’re writing for. 
• Have fun with it and throw in some puns or try adding in an emoji.



4. Keep it simple

Sometimes the perfect headline is just a simple few words that tell the story.

A famous Albert Einstein quote reading “If you can’t explain it simply, you don’t understand it well enough.”

5. Don’t get caught up in the moment

Be careful of going too far off the reservation and making something so different that only a few people will understand it.



6. Don’t just settle on one

It used to take more than 30 masters of the word shouting a lot of outrage, love, poetry, and more to craft the perfect teaser and there used to be a lot of different ideas.
Speak your headlines out loud and make sure to tell your dog or anyone else who will listen and keep the ones that they responded well to.

7. …and the best for last is to test and eliminate the ones that don’t work

This is the biggest one that will always surprise you at which headline would work best. Take a couple of options and put them out there and if something is not performing, drop it, change it and move on.

8. Bonus one…The hardest lesson I keep on having to learn

Don’t get attached to a piece that you might have spent hours crafting and has your heart and soul behind it. If it’s not working, move on. 
This one does not get easier over time!

I have a book full of billboards, stories, and other fun stuff that the team put together for me when I left the newspaper.
Get in touch if you would like to take a trip down a colourful memory lane of intrigue and many laughs.


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