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We all know that headlines are important to any content that is written out there, right?

Between 2 articles that have almost the same kind of content inside (which is the case especially with list posts), who do you think would win the open rate?

The one with the better headline, of course.

But, before you start going “oh, this is just one another of them headline posts,” you’re partially right.

And partially wrong.

But why is this guide different?

Because some of the steps I show you here, I have to see any (yet).

And in my 6 years of writing content, I still see certain methods that haven’t been used (yet).

In this article, I’ll bring to your attention 5 different headline methods that I use personally to draw endless attention and praise to my articles – for years on end.

At the end of this post, you should at least have a clear idea of how to go about crafting really thought provoking headlines that will attract your reader’s attention the same way my posts do.

Let’s begin!

#1: Begin by analysing your prospects’ personality

It’s no secret that understanding who you’re talking to allows you to write better headlines that get them to open.

In fact, Ramit Sethi has been saying this for the longest time:

“In this crowded world, if something isn’t built specifically for me, I’m gone.”

How true can you get?

Yet, this is a simple truth that many people miss.

So often in my career, I’ve seen people that write without having a clue who they’re talking to, when it could be the make or break factor between a Unique Open, and the trash bin.

By now, if you’re an experienced blogger, you should know that you should always visualise someone sitting across the table when you’re writing.

This does 2 things:

  • It makes your content more personable
  • It makes your content more engaging, because are actively trying to involve them in the conversation

While everyone’s talking about applying that to your writing, why not apply it to your headline, at the same time?

This is surprisingly easy to do.

Step 1:

In order for us to analyse our target audience’s profile, you will need some analysis tools on your side .

In this case, I like to use Crystal, which is an online personality assessment tool that pulls data from text, analysing the patterns behind it, and then churns out a large possibilities of ways for you to communicate with that person.

The first thing to do is to install the Crystal chrome browser extension.


Crystal positions itself as a social media personality platform, where you can analyse anyone’s personality, with a “credit”.

It uses different areas of writing from a particular individual’s social media and web presence online, to pull together different patterns that might show us how a particular individual is in terms of his personality, flair, and how he/she communicates with that individual.

The first thing that we have to do is to install Crystal on Google Chrome Extensions.

To access the Extensions Store, we click on the Google Chrome Dashboard options>More Tools>Extensions

Scroll to the bottom of the page, and click on Get more extensions.

Type in Crystal on the search bar on the left hand side, and click on Enter, and Crystal should start installing.

Once Crystal is installed, you’ll see Crystal’s icon appearing on the right hand side of your Chrome Dashboard, something that looks like this.

Click on it, and you’ll see a popup on the right hand side, that looks like this:

In order for us to start using Crystal’s text analyser tool, we need to sign up for a free account with Crystal first.

Click on the Login To View Personality button, and you’ll be redirected to Crystal’s sign up page.

Sign for an account if you don’t already have one, or login with your email and pass.

If you are new to Crystal, you will be prompted to answer some basic assessment questions.

This is so that Crystal can understand your profile better, and come up with a list of suggestions on how best you will be able to work with someone else.

Once you are done with the questionnaire, click on Finish and See Results.

Once you have successfully setup your account on Crystal, it’s time to put the text analyser tool to work on 3 potential readers of your blog or brand.

Step 2:

The next step that we need to do is to find 3 people who you are interested in writing to.  

Some ground rules before we proceed here:

  • Before we continue, make sure that these people have at least written content somewhere before, such as their blog, their LinkedIn profile, and so on
  • Have a blank document ready somewhere – we will use this to note down our study of your readers’ personalities

The best way to do this is via Linkedin.

Go to LinkedIn, and click on the Advanced Tab.

This will redirect you to the Advanced Search function of LinkedIn.


Next, type in the keywords that you are trying to appeal to.

For example, if you are in the tech area, one good keyword to use is the keyword “marketing”.

Select the location of the reader. For this example, I will use United Kingdom as my main search term.

Then click on Search.

LinkedIn will pull up a list of people with the keyword ‘Marketing’ in their profile, and who are situated in United Kingdom as well.

LinkedIn will filter the results according to the keywords that you have identified.

The next step that you want to take is to head over to their profile, and grab a hold of their content.

Let’s say we choose to go with Victoria Scally.

Since Crystal disabled the free LinkedIn credit analysis recently, you can use a simple workaround.

The first step is to copy the text that you see in Victoria’s profile.

Next, we will want to open up a new tab, and go to Google.

Then, click on the Crystal extension on the right hand corner, and copy and paste the sample text that we obtained from Victoria earlier into the Text analyser.

Crystal will then churn out a list of personality traits that this particular individual has.

An important section to note is the section under Building a Relationship With this person, and Communicating with this Person, because these will reveal the type of content and headlines that will get their attention:

Note down the following:

  • What common features do these people have in common?
  • What are the best ways to communicate with these people?
  • How can I write a headline that can make these people click on?

Repeat this process for as many prospective readers that you want your headline to stand out to, and note down your progress on the blank document.

Note: If you need help in creating a powerful LinkedIn profile that converts, you can check out exactly how here.

#2:  Find your audience’s deepest fears, needs and desires

There are the things that people want, and there are things that people need.

For this case, this is even true when it comes to our deepest fears.

For example, here’s what a Want for an entrepreneur might look like.

  • I want to be successful and I want to have a successful business, therefore I own a business and am an entrepreneur

Now, this is common. That’s why we all own a business, right?

But this is not just what your headlines should focus on.

Your headline should focus on the deepest fears, AKA the Needs of the person that you are trying to appeal to:

Some common forms of Needs might go something like:

  • I’m afraid to work for people
  • I’m afraid to tell people that i’ve failed
  • I’m afraid that one day I’ll wake up and all my work is wasted, and I have to start from scratch

You see the difference?

The power of Needs and Wants in headlines is very real, and not one that you should ignore at all.

That’s why people buy programs that teach entrepreneurship. That’s why people buy tools that promises conversions.

Because these are tools and marketing messages that subtly nudge us away from our Needs – they tell us that everything will be alright when we have their tools.

The thing is, no one really talks about their insecurities, and their deepest fears.

You have to intimately understand your audience in order to really figure that out.

Lucky for you, you can follow the steps below to get started.

#1 Do a one on one session with your existing clients, if you have any

Many of us start a website/blog when we already have a list of clients, or someone that we’ve worked for in the past.

Often times, because this group of people have already worked with you before, they are much more open to talk about their insecurities,  and why they think you can help them.

For starters, you might ask something like this;

  • Why did you think, before you hired me, you had to solve this problem?
  • What do you think is your biggest problems right now in your business?
  • Ideally, if you could have the best day of your life, how would it look like?
  • If you had the worst day of your life, what would it look like?

At this point, you are simply trying to understand the minds of your audience, and what makes them tick.

The key thing is to dig as deep as you can, without sounding too intrusive about it.

Make sure to thank them for their time after your conversation – who knows – they might even rehire you again since you brought up the topic.

Note: Keep in mind that this group of clients might be your most loyal, if you consistently create content to answer all their questions. Make sure they are the first to know when you launch new content.

#2 Do an insecurity contest.

There are a lot of contests out there,  and they happen to be one of the most highly converting forms of marketing out there.

So, why not do an insecurity contest?

An insecurity contest is simply a contest where participants can stand a chance to win prizes that are relevant to your niche, in exchange for sharing their deepest thoughts about their problems.

To do so is relatively simple.

  1. Set up a contest landing page – you can choose either Lead Pages or Vyper, or even host the contest on your own site, if you want.
  2. Be very specific with the requirements of the contest – you don’t want people to overdramatise their problems just so that they can win. Make sure that every entry is treated equally.
  3. Launch a Facebook campaign by running some ads, or, if you have an email list, send it out to them, and direct all the traffic to that specific landing page

The contestant(s) that wins the contest gets some freebies and goodies.

As for those that don’t win? Well, here’s a tip, keep them in your mailing list anyways, since these people have already indirectly requested for solutions to their problems already!

Remember to keep all submissions a secret and not public, so that the responses are more genuine.

Final Step:

Once you get the responses, you’re ready to move on to the next step of actually crafting the headlines.

For example, if you’re trying to create a headline that appeals to audience who said they were afraid of failing and going back to work, you can come up a headline that looks like this:

“How to stay away from business failure, shut off all negative thoughts, and live free”

That’s a sure winner!

#3: Use Headline generators

Obviously, in order to come up with really powerful headlines, you need to have as many suggestions as possible.

Again: some ground rules before we begin this step:

  • Have a document ready on standby (you can use the document that you continued from Step 1 here
  • Write down and note down the different headlines that you feel are worth considering down in list form

To start generating some headlines, we can use the Portent Tool to generate some really powerful headlines.

Portent Headline Generator

Head over to Portent, and type in the keyword that you are trying to rank for.

For example, suppose I am trying to rank for business failure, I will just type in “business failure” into the search bar.

Then, click on Generate.

Portent will generate different headlines that are both interesting and useful.

Hit enter to view the next headline that Portent generates.

Next, note down the most interesting headlines that you think might appeal to the personalities that you’ve researched on earlier in Step 1.

Remember the section under: Ways to communicate with? This is a great time to use this section to filter out the headlines that will work, and those that won’t.

Link Bait

The next tool that we can use is called Link Bait, and, as the name suggests, it’s a tool that generates a list of headlines that you can use for your content.

Link Bait works relatively the same way as Portent.

To start off, enter the keywords that you are trying to rank for (in this case, “business failure”), and Link Bait will generate a ton of titles that you can choose from.

Again, remember the personalities that you’ve just discovered, and the ways to speak to them.

What do you think are keywords that people like them will search for?

For example, if I were trying to speak to a estate agent marketing professional, but my ideal readers are Type A personalities, who focus exclusively on results, having a headline like “30 ways to help you market your estate agent content” might not work as well as ”The Extensive Guide of “Results Driven” 30 Tools to Distribute Your Content”.

You see the difference? If you are a marketer who’s focused on generating results day in and day out, which headline would you click? Probably the second one.

Select the headlines that work best for you, and note them down into your document.

#4: Instant value approach

What happens when a prospect or search browsers through the web or screens through their social media channels?

They scroll for things of benefit and value to them.

If you look at it from that point of view, it’s quite obvious how you can get their attention, isn’t it?

By instantly showing them value in your headline.

You can do this the following ways:

  • By including statistics, figures and findings that are related to the reports
  • Including some real-world case studies and examples
  • Pointing out the instant benefits that audiences get, for example “The 30 step guide to Creating a Powerful LinkedIn Profile that Converts Insanely”.

Neil Patel recently did a case study about analysing over 18,000 headlines, and the common characteristics of the most powerful headlines that he found was:

  • They tend to include some form of statistic in them
  • They tend to provide value up front
  • Mention videos in your headline
  • Polarizing topics gain high shares
  • The length of the highest engaging headlines is 16-18 words

What does this analysis tell you?

That by showing the value in your headline, you are summarising the potential value that your audience can get from your content.

In short, showing the value first creates a certain certainty in content that will set your content apart from the sea of competition that’s out there.

You can show the value in your headline by keeping these questions at the back of your head the next time you try to create a valuable headline:

  • I know my content is valuable, but how can I summarise it in my headline?
  • Is there any statistics that I can use to promise some kind of benefit to my readers?
  • Why should my reader read my content, when there are already tons of information out there?

#5: Use power + trigger words

By now, you should have completed Step 1-4. If you haven’t, go back and finish them before proceeding to this step.

This is the final step of this unconventional guide, and I do hope you are still with me so far!

The next step that we have to do is to include some power and trigger words into our headlines, so that the emotional appeal of the headline increases.

What do I mean?

Trigger words and power words are emotional words that touch on the hot buttons of your readers, and is closely linked to the needs, wants, fears and desires of your target readers.

They are the words that raises that heart rate of your audiences, and significantly increases their level of interest in your article.

For example, have you ever wondered why all sales are RED HOT?

Why is buying insurance for your LOVED ONES, when in fact, you are insuring yourself from an accident?

You guessed it.

Trigger Words are just that. They are simple, but effective words that writers use to gently nudge the reader off a cliff, and get them to focus on the content.

Here are a list of trigger words that you should have seen before:

Assembling your headline together

By now, you should have the list of power words with you, that you can put to use immediately on your headlines.

The next step is putting together a headline that will impact your readers with maximum impact.

When you are choosing your power words, make sure that you are constantly asking yourself these questions:

  • Given the personalities of my targeted readers (step 1), what words would really stand out to them?
  • Given the insecurities and hopes that my targeted readers have, what words would catch their attention?

Once you’ve chosen your power words, it’s time to assemble your headline together.

When you are writing your headline, there are a few ground rules that you should take note of:

  • Your headline should ideally be between 18 words maximum
  • You should always aim to put your keyword in your headline
  • You should try to put your keyword as close to the beginning of your headline as possible

These technical steps help you to rank for SEO, so make sure you at least pay attention to change some of these specifics.

Don’t just try it 25 times, try it till it’s foolproof

Upworthy have made quite a name for themselves when they famously made it a part of their editorial process to test their headlines 25 times.

While this might be effective to some, I would say that from personal experience, test out your headline until it’s totally foolproof.

How? Let’s go through 2 simple ways that you can do so.

Coschedule Headline Analyser

The first method that we can test our headline’s effectiveness is by using the Coschedule Headline Analyser that is free to use.

For example, if my headline that uses the word “shocking” scores only 61 on Coschedule, I might want to consider using the word “Amazing” instead, which would make my headline score bump up to 73.

Ideally, you’d want to get your headline to above 75, but again, you know your audience best.

Generally, I advise my clients to use something we’re all born with. Common sense.

If you know that the headline will most definitely work, then don’t scrap it because of SEO reasons.

Test it with your friends or family

Summon the best minions at your disposal. Your friends or your family. I’m kidding.

Friends and relatives have that unique ability to be objective, yet subjective at the same time. It’s very strange.

Anyways, they make perfect testing beds for your headlines.

Simply come up with 2 or more headlines, or, if you think by now, you have a winner, test it on them with the following questions:

  • Taking a look at this headline, what do you think this content is about?
  • Do you think this content will be valuable, without seeing the article?
  • On a scale of 1-5, 5 being the most interested, how interested would you be to click on this article?
  • What problems do you think the article solves?

Based on their responses, you might want to follow up with questions like:

  • What do you think can be improved in the headline?
  • Why don’t you want to click on the article?
  • What do you think is missing from the headline?


At every step of the way, be sure to keep in mind the type of audience that you would like to attract.

Quick Note:


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Having a clear idea of the type of people that your headline attracts, and phrasing your headlines in a way that appeals best to your desired audience is to most fundamental steps to crafting powerful headlines that convert, time after time.

What other ways of headline writing did I miss out?

Are there any other methods that you would like to share? Comment down below! I’ll help everyone’s content marketing out. 🙂

John Chen

John Chen

Founder, Head Content Guy at Contentrific
John has helped professionals from multinational corporations like Microsoft and Accenture scale their personal brands with the right content.
John Chen

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