During StoryConnect 2024, Pioneer SVP of Content Leon Espinoza led five brainstorming sessions for writers struggling with headlines. He gave everyone a headline handout, which we used to write this blog post (with Claude AI’s help and Leon’s guiding vision).

We’ve all been there — you spend hours crafting the perfect blog post, article or story, only to get stumped when it comes to writing that all-important headline. The headline is the first thing readers see, and it needs to grab their attention and convince them to read more. But how do you consistently write headlines that jump off the page?
Never fear, I have three simple tricks up my sleeve that will have you crafting clickable, compelling headlines in no time.
1. Keep It Simple and Conversational
The best headlines use simple, conversational language — kind of like how you’d describe the topic to a friend over coffee. Ditch the jargon and overly complicated phrasing. Your headline should be easy to read and understand at a glance.
Consider using questions, commands or “how to” phrases to make it feel like you’re having a friendly chat with the reader. For example: “How I Finally Kicked My Afternoon Sugar Cravings to the Curb” or “Declutter Your Closet in 5 Easy Steps.”
Writing great headlines is both an art and a science. Follow these 4 “Ks” to set yourself up for success:
- Keep it simple — Don’t try to tell the whole story, just enough to pique interest.
- Keep it real — Use conversational, natural language.
- Keep it short — Most readers only spend seven seconds scanning a headline.
- Keep it up — Great headlines evolve over time through revisions.
2. Ready to Write?
With our ever-shrinking attention spans, you only have a few seconds to hook readers with your headline before they move on. Stick to around six to eight words, or 60 characters max, to ensure your headlines are tight, punchy and memorable.
One trick is to start by writing a longer “dream headline,” then ruthlessly edit it down to just the essential, high-impact words. You can also try spinning your pen while brainstorming — the movement may just unblock creative gems!
Think about what emotion or feeling you want to evoke in readers from the get-go. Do you want them to feel curious, inspired, amused? Let that guide your word choices and use vivid, attention-grabbing language.
Strong verbs and adjectives work wonders. Another tactic is to tease readers by hinting at the story or benefit, without giving too much away. Remember:
- Dream big first, then pare it down to just the essential, punchiest words.
- Tease the reader by hinting at the story without giving everything away.
- Evoke emotions and stir curiosity right from the headline.
- Put yourself in the reader’s shoes. Why should they care about this topic?
- Play off any visuals, and let compelling images guide the headline.
- Describe it like you would to your best friend using plain language.
- Consider the headline even before drafting to provide a focal point.
- Use action verbs and “What/How/Why” phrasing to clarify the benefit.
3. Fight Writer’s Block
Even seasoned writers struggle with headlines sometimes. When you’re stuck in a rut:
- Brainstorm and bounce ideas off others for fresh perspectives.
- Go for a walk — a change of scenery can shake loose new ideas.
- Do a mundane, repetitive task like spinning a pen to unlock creativity.
- Consult a thesaurus to find just the right impactful word.
- Look to other writers for inspiration but avoid copying verbatim.
Don’t be afraid to loop in some AI assistance when you get stuck! Feed your draft post or story into a headline generator tool and see what quirky options it spits out. You’ll often find unexpected word combinations or angles that can spark new ideas.
Just be sure to fact-check any auto-generated headlines and put your own creative spin on things. AI is great for drafting thought-starters, but you’ll still want to put your unique human touch on the final headline.
The more you practice and experiment with different styles and formulas, the more skilled you’ll become at crafting magnetic headlines. Keep at it and have fun playing with words! Before you know it, you’ll be a headline-writing pro.
We uploaded Leon’s headline tips sheet to Claude.ai, with a prompt to write a 600-word blog post using the bullet points (PDF) to create a summary of each point. Pioneer’s team reviewed and edited the result. Then, Leon reviewed the post and made edits to ensure it matched his voice. Thinking about how AI can help you tell stories more efficiently? Learn what your peers think.
