How to Write Headlines That Actually Get Clicked

Want More Readers? Start With a Better Headline.

For 10 months, I wrote in silence.

I poured 2+ hours into every post—only to watch them vanish into the void.

The engagement was nonexistent. No likes. No shares. I may be biased, but it’s not because they were bad. It’s because no one even clicked to read them.

What changed everything? When I started giving them a reason.

I stopped writing articles first—and I started writing my headlines first.

And that one shift? Sparked life into my publication. Increasing my views, increasing my shares, and even made my writing easier.

In this post, I’ll walk you through the exact 5-step system I use—plus the AI prompts that help me create headlines people can’t ignore.

---

Headline First, Article Second

A mentor of mine once said something I’ll never forget:

“Don’t start with the copy. Start with the idea. Start with the headline. Spend more time here, and let the copy follow.”

That advice is now pinned at the top of every Substack draft I write.

Why?

Because the headline isn’t just a title.

It’s the subject line. It’s what drives SEO. It sets the frame for the entire article. But most importantly, it’s the reason people click (or don’t).

Before, I’d write the full article and slap on a title at the last minute. Oftentimes using generatic AI-generated ones.

But a headline written after the fact usually doesn’t match the message—it feels like an afterthought.

Once I made this shift, I realized I needed a repeatable system—something I could rely on for every post.

That’s where these 5 questions came in.

---

Answer These 5 Questions To Craft A Great Headline Every Time

That’s when I created a simple framework I use before I start writing.

I call this my “Big Idea Planning.”

It’s just 5 questions. But they shape the direction, angle, and headline of every post I write.

Here are the 5 questions.

1. What’s the general idea of the post?

2. What numbers of specifics can I add?

3. What common assumptions can I challenge?

4. What’s the promise I am making?

5. What story or personal experience can I infuse?

Originally, I built this process to create headlines, but I quickly found it helped me write better articles.

As my mentor taught me.
It’s not just the words in the article but the purpose of the article.

This was the lightbulb moment for me that unlocked my ability to start writing things that people wanted to share.

Here’s a rough outline of the “Big Idea Planning” I used for this article.

Question 1: What’s the general idea of the post?

• 5 steps to create a winning headline for your Substack article.

Question 2: What numbers of specifics can I add?

• 5 steps.

• Uses ChatGPT.

• 15-30 Minutes or less.

• Repeatable process.

• 200% increase in my post views.

Question 3: What common assumptions can I challenge?

(Alternatively, you can ask what commonly held beliefs you can contrast)

• Basic ChatGPT prompts are good enough.

• AI can’t write headlines.

• Use your post content (after) to write your headline.

• Ask ChatGPT for 10 headlines.

Question 4: What’s the promise I am making?

• Create a winning headline in 15 minutes or less.

• Answer these 5 questions to craft a winning headline every time.

• Write headlines that get your articles clicked.

Question 5: What story or personal experience can I infuse?

• My highest viewed articles have the best headlines.

• My articles started to get more views (and shares) once I started improving my headlines.

• The lesson I learned from a writing mentor to spend 80% of my time on the idea and headline and 20% on the copy.

• Writing the headline first makes the article easier to write.

This is now the first step I take in writing every article.

Then, I use that information with a simple 5-step ChatGPT prompt to craft my headline.

Here are the exact AI prompts that I use.

---

The AI Headline System That Helped Me Increase My Views

Generic headlines are killing your Substack.

Here is my 5-step headline flow:

1. Generate 30-50 headlines using our “Big Idea Planning.”

2. Grade each headline.

3. Short list the top 3-5.

4. Ask ChatGPT to critique them.

5. Compare them to your historical top headline format.

Let me walk you through the process.

Step 1: Generate 30-50 headlines using our “Big Idea Planning.”

Using our “Big Idea Planning,” we feed it into ChatGPT to generate headline variations for us to work with.

I find it more effective to generate 30-50 headlines using various angles compared to 10 (what I used to do) because it allows for greater variety and creative approaches.

The Prompt:

Assume the role of my ghostwriter, specializing in writing viral titles and hooks.

Generate a list of 30 viral titles. They should vary in approach. Some should be contrarian. Some should challenge assumptions. Some should be clear and simple. Some should be speak to one person about one problem and offer one solution. Some should be a single declarative statement.

Here is the information for the article:

[Insert Big Idea Planning]

Examples:

Here are a few headlines I generated for this article.

• You Don’t Need a Better Article. You Need a Better Headline.

• How to Write Headlines That Actually Get Clicked.

• Answer These 5 Questions to Craft a Great Headline Every Time.

• Want More Readers? Start With a Better Headline.

• Headlines First, Articles Second (Trust Me on This).

Pro Tip:

I like to use my “runner up” headlines or headlines that I thought were solid as my subhead, hooks, or titles for sections (when relevant).

Step 2: Grade each headline.

Now, we have a list of 30-50 headlines using various formats and structures.

In Step 2, we want to grade each of them using two free tools.

I like using two tools because they grade them based on different criteria, so I look for headlines that rate high on both. Additionally, there are other tools you can use, but I use these two because they are free (and accessible to everyone).

The Tools:

• https://www.aminstitute.com/headline

• https://www.monsterinsights.com/headline-analyzer/

Pro Tip:

Before grading them, I like to highlight the headlines that I think are the winners. Over time, this trains my brain to spot and recognize top headlines.

Step 3: Short list the top 3-5.

With all of our headlines graded and scored, we narrow them down to the top 3-5, creating a shortlist that we will use in Step 4.

I like to find headlines that score >30 on AMI and >70 on Monster Insights.

Pro Tip:

We must also apply our unique experience and understanding of our audience to our selection process. Just because a headline has a high score doesn’t mean it is the most aligned headline to use.

Sometimes, I will find headlines with very high scores that don’t capture what I want to communicate or aren’t aligned with the vibe in which I write.

Step 4: Ask ChatGPT to critique them.

Now, we ask ChatGPT to critique our shortlist.

This process allows us to see why each of them is good and where it might fall short (ex: lack of specificity). From here, we can refine and improve or maintain our initial selection.

The Prompt:

These [INSERT NUMBER] are my favorite. 

Please provide a critique for each of them.

Here is my shortlist:

[INSERT SHORT LISTED HEADLINES]

Pro Tip:

This can help us reveal blind spots that we may not have considered. ChatGPT does a fantastic job of auditing and critiquing its own work. Even if you don’t implement its suggestions, it provides valuable feedback.

Step 5: Compare them to your historical top headline format.

Consider this a bonus— a great step, but not required.

I like to provide a spreadsheet of my past articles and headlines (including engagement) and ask ChatGPT to compare these headlines to my historical top performers.

If a specific format or style has been shown to work well for me in the past, I like to repeat what’s been proven to work.

If you’d like to do this, you can find my exact Substack Post audit I use to find my top performers in a post I wrote called How ChatGPT Revealed the Secret Formula Behind My Top Substack Posts

The Prompt:

Please review the titles from my top posts here. Top views and engagement. Then tell me which of these [X] titles best matches the structure of my top posts.

Along with this prompt, I include the spreadsheet of my post data.

ChatGPT proceeds to review the headlines of my highest engagement articles and compare them to the short list we’ve created.

Pro Tip:

Set time aside this week to follow my Substack Post Auditing process so you can follow this step and increase the effectiveness of your headlines.

Click Here To Read The Full Guide.

Lastly, Choose Your Winning Headline.

Now, we choose our headline (title) for our post.

I like to choose my second favorite as my subtitle, and often times I will have other random titles or suggestions from it’s critiques that inspire completely new articles.

---

After 10 Months of Nonexistent Growth, I Always Write the Headline First—and I Think You Should Too

For 10 months, I wrote posts no one read.

Not because of my writing—but because no one clicked. No one had the opportunity to read what I wrote.

Writing the headline first didn’t just increase my views. It made my articles easier to write. Every post felt more aligned, more focused, and more shareable.

Headlines aren’t just titles.

They’re what make someone stop scrolling.

They’re the reason your articles get read or scrolled by.

If you want more people to read your work, start with the headline.

Try this once, and you’ll feel the difference.

Try it consistently, and it’ll change the way you write.

Hope this helps.

Landon

---

Want to monetize your Substack quickly—even without a product idea?

In Subliminal Selling, I’ll give you my straightforward 3-step process to pinpoint exactly what your readers want, create a profitable digital product with zero-cost tools, and make your first sale in record time.

Your first dollar awaits. Click here to claim it.

---

PS: If you found this helpful, would you do me a quick favor and restack it? Sharing spreads the message and motivates me to keep writing practical content to help you thrive in your online business.