Are You Leaving Money on the Table with Weak Headlines?

Your headline is the epic gateway to your content. Are you doing everything you can to pull your readers across the threshold?

Tune in to hear from two Copyblogger heavy hitters (and serious headline nerds) — Pamela Wilson, Executive Vice President of Educational Content, and Stefanie Flaxman, Editor-in-Chief.

They bring along a satchel full of tips, techniques, and tools that will help you create killer headlines that get clicks from the right readers.

In this episode, Stefanie and Pamela talk about:

  • Why headlines matter more now than ever before (it goes beyond just getting clicks)
  • How much time you should spend writing your headlines
  • Two innovative tools and one indispensable resource you can use to write strong headlines
  • How you’ll know when you’ve hit on a headline idea that works


The Show Notes


Are You Leaving Money on the Table with Weak Headlines?

Jerod Morris: Hey, Jerod Morris here. If you know anything about Rainmaker Digital and Copyblogger, you may know that we produce incredible live events. Some would say that we produce incredible live events as an excuse to throw great parties, but that’s another story. We’ve got another one coming up this October in Denver. It’s called Digital Commerce Summit, and it is entirely focused on giving you the smartest ways to create and sell digital products and services. You can find out more at Rainmaker.FM/summit. That’s Rainmaker.FM/summit. We’ll be talking about Digital Commerce Summit in more detail as it gets closer, but for now, I’d like to let a few attendees from our past events speak for us.

Attendee 1: For me, it’s just hearing from the experts. This is my first industry event, so it was awesome to learn new stuff and also get confirmation that we’re not doing it completely wrong where I work.

Attendee 2: The best part of the conference, for me, is being able to mingle with people and realize that you have connections with everyone here. It feels like LinkedIn live. I also love the parties after each day, being able to talk to speakers, talk to other people who are here for the first time, people who have been here before.

Attendee 3: I think the best part about the conference, for me, is understanding how I can service my customers a little more easily. Seeing all the different facets and components of various enterprises then helps me pick the best tools.

Jerod Morris: Hey, we agree. One of the biggest reasons we host the conference every year is so that we can learn how to service our customers — people like you — more easily. Here are just a few more words from folks who have come to our past live events.

Attendee 4: It’s really fun. I think it’s a great mix of beginner information and advanced information. I’m really learning a lot and having a lot of fun.

Attendee 5: The conference is great, especially because it’s a single-track conference where you don’t get distracted by, “Which session should I go to? Am I missing something?”

Attendee 6: The training and everything — the speakers have been awesome — but I think the coolest aspect, for me, has been connecting with both the people who are putting it on and then the other attendees.

Jerod Morris: That’s it for now. There’s a lot more to come on Digital Commerce Summit. I really hope to see you there in October. Again, to get all the details and the very best deal on tickets, head over to Rainmaker.FM/summit. That’s Rainmaker.FM/summit.

Pamela Wilson: Welcome back to Copyblogger FM, the content marketing podcast. Copyblogger FM is about emerging content marketing trends, interesting disasters, enduring best practices, along with the occasional rant. If you are a loyal listener, you’ll notice right away that I am not Sonia Simone. My name is Pamela Wilson, and I’m the Executive Vice President of Educational Content at Rainmaker Digital. Sonia asked me to sit in for her this month. Today I’m here with my colleague, Stefanie Flaxman, the Editor-in-Chief for Rainmaker Digital. Hi, Stefanie.

Stefanie Flaxman: Hi, Pamela. Thank you for having me.

Pamela Wilson: I’m so glad you’re here. I cannot wait to get started with this topic that we’re going to talk about, because it makes such a difference if people can get this piece of their content right. For listeners, if you’ve heard this podcast before, you know that Sonia always says, “I hang out with the folks who do the real work over on the Copyblogger blog.” Guess what? We are the folks who do the real work over on the Copyblogger blog. Stefanie and I manage the blog. Stefanie, you’re really the one who’s on the front lines. You’re doing the bulk of the work. But we work together on the content that we put together.

We’re going to talk about headlines today. This is something that you and I are both passionate about. We have lots of email and Slack conversations about headlines that we’re editing. It tends to be something that we change a lot in our content, and we are passionate about creating these headlines that are very clickable and that are irresistible. It’s what we’re known for on Copyblogger, so you and I spend a lot of time on it. I think it’s going to be a great episode. Are you ready to dive right in?

Stefanie Flaxman: I am so ready. Passionate is the nice word, because it’s like serious headline nerdery.

Pamela Wilson: Yes.

Stefanie Flaxman: I’m also very excited because we just love this topic.

Pamela Wilson: It makes such a difference. I think it’s where the relationship with the reader begins. It’s that opening bang that you can make that will attract attention from them and hopefully extend the reach of your content, motivate people to dive in and start reading. The thing about it is, we all know that content marketing is the smart thing to use to promote your business, but content marketing doesn’t actually work if people don’t find your content and read it and take action. Headlines are one of the things that make a difference. They make people want to dive in and consume.

Stefanie Flaxman: Yeah, it’s no different than news headlines. In content marketing for a business — it’s not breaking news in the world or your city or anything like that, but it’s that same idea of, “How do you immediately communicate in a clear way to who you want to speak to.” Whenever I’m on with Sonia, I always make this disclaimer that I’m going to probably bring up a lot of Copyblogger posts for reference because that’s what I look at all day long. I’m already stewing with, “Ooh, I could talk about that post and this post,” and things like that. We have show notes for Copyblogger FM, but if anyone wants to write it down, I will probably be mentioning the headlines of certain posts as we talk about examples.

Why Headlines Matter More Now Than Ever Before (It Goes Beyond Just Getting Clicks)

Pamela Wilson: As illustrations. I think that’s a great idea. I always tell you, you’re like the walking encyclopedia of all the Copyblogger content. Stefanie’s one of those people that you could say, “Didn’t we have a post 4 years ago,” and she can come up with it in about 15 seconds. I love what you just said, and I think this is so important. I don’t know that people talk about it enough. The fact that a headline not only helps your content to get the click and to get read, but if it’s working right, your headline will actually attract the audience that you want to attract to your content. That’s important because when there is a match between the reader and the content that you are serving up, that’s when things start to get really interesting.

Stefanie Flaxman: My first example — because this is exactly what I was thinking about — was a post that will have been published recently on Copyblogger at the time when this podcast episode goes live. It is called “3 Smart Moves that Supercharge Sales Funnels with Content.” I won’t give away the whole post there, but one of the main points is attracting the right people to your content. Headlines are really powerful for that.

You could have an amazing headline that you think would just attract a wide variety of people, which is great. There is a time and a place for attracting attention. But if you attract a lot of attention but none of those people are actually interested in what you sell, if they’re not interested in the rest of the content you produce because this one viral post — I don’t like the word viral — this one post with a broad appeal doesn’t apply to who you’re actually selling to, the results will fizzle out. Having a focused outlook when you’re crafting headlines to who you’re speaking to is where you want to go with that for your business, rather than, “What’s going to make everybody like what I’m writing?”

Pamela Wilson: Exactly right. It’s not about making everyone like your content. It’s about making the right people like your content. I love that you brought up sales, because I do think that’s an important thing to think about when you’re writing a headline. When you write a headline it is not a time to be shy. I think you have to get comfortable adopting a little more of a sales-y tone to the copy that you’re writing, because honestly, that headline is out there in the world advocating for your piece of content. It really is selling the piece of content that you wrote. As long as your content is excellent, you should not feel embarrassed about giving it the best possible chance to be discovered by taking the time to write a headline that really has impact and makes people want to click.

How Much Time You Should Spend Writing Your Headlines

Pamela Wilson: Let’s talk about some dos and don’ts so that people — hopefully they’re fired up to write amazing headlines at this point. Let’s talk about some real dos and don’ts and get into some tools that you and I use and techniques that we’ve discovered that work pretty well. When it comes time to write a headline — in comparison to the amount of time that you spend writing your content, and this is totally an estimate — what would you estimate would be the amount of time that you would spend writing a headline versus the amount of time you spend on the content?

Stefanie Flaxman: I don’t want to say they’re equal, that’s a terrible overestimate. But there is a lot of time spent on the headline — 20 to 30% of the total time, probably. It sneaks up on you, that time that you spend, if you’re really fine-tuning and finding the precise, exact words that you need. Not to say that the rest of the article doesn’t have that same energy and passion and focus, but you don’t want to miss an opportunity to speak to who you need to speak to and hook them in so that they read the rest of your content.

Pamela Wilson: Right. That’s such an important point. You don’t want to leave this as one final touch that you’re going to put on your content. You want to really devote a lot of time and energy. Now, there are times that you come up with a headline — it’s happened to me before that this headline has dropped out of nowhere into my brain, and I’m like, “Oh, I need to write that post.” You get a headline almost like a gift and then you write a post for it. Then there are other times that you spend so much time. You’ve got a great piece of content. Maybe you started out with one headline and you’re not happy with it anymore, and you just find yourself generating all these different ideas until you come up with the one that works.

The one thing that I wanted to say is that if you spend a lot of time writing headlines, that time is not necessarily wasted, because we also encourage people to write subheads in their copy. Sometimes you come up with a headline that’s okay, but maybe it’s not the best one you came up with. There might be a way to repurpose either the exact headline or some concepts from the headline in some of the subheads in your piece. It’s not time wasted. I think you can always put that content to good use. Now, are you a believer in writing the headline before the content? I know there are different schools of thought on that.

Stefanie Flaxman: I am. It’s like what you were just saying, at least a rough headline. It doesn’t have to be the headline that you end up using, because new ideas could come up when you actually write the piece. It might go in a different direction. There are two questions that I always like to think about when I’m coming up with a rough headline, and the answers to those questions don’t necessarily go in the headline. They might not even … Yeah, actually, usually they don’t go in the headline, but it’s a reference point when you go through your article when you’re done writing, you can refer back to the answers to these questions to see if the headline idea that you have really is spot on with what the content is. These questions …

Pamela Wilson: Okay, now I’m dying to hear these questions.

Stefanie Flaxman: Yeah. I do.

Pamela Wilson: They sound powerful.

Stefanie Flaxman: Sometimes the headline completely changes, but yeah, I have to reveal what the questions are. If I have an idea for a content — just a rough idea — I’m like, “Okay, I’m going to write this article.” I ask myself, “Who am I talking to and how do I help them?”

Pamela Wilson: Oh, that’s so great. So simple, but so great.

Stefanie Flaxman: So it’s really simple. You can write all those questions without thinking in terms of a headline format at all. Just answer those questions. They’re in your back pocket, and then you can go along and write your article and draft headline ideas. That’s really what it’s about with content marketing. You’re making these individual connections and you’re helping people to move them along. Get them familiar with your business. Show that you have a solution to the issues and the problems that they’re struggling with. Yeah, the words in those answers, again, don’t necessarily go exactly in the headline, but they’re your foundation to go back to.

Pamela Wilson: I love that. Even if you don’t write the headline first, if you at least have the answers to those questions, that’s going to help you. I usually recommend people try — it’s not always possible — but that they attempt at least to write a headline before they start writing. The reason I do that is because I think it helps you to clarify your thinking about the topic you’re about to write about. I know that it has always helped me to come up with some good headline ideas before I start writing content, because what tends to happen is if I come up with a headline I’m really excited about, then I start to feel really enthusiastic about writing the piece of content. I’m like, “Oh, I can’t wait to write this one.” It can have that effect. When you come up a really great headline, it can have that effect of injecting a lot of energy into the content creation process.

Two Innovative Tools and One Indispensable Resource You Can Use to Write Strong Headlines

Pamela Wilson: I want to cover tools, because I think it can be really helpful to have a set of tools that you keep at hand when you’re doing this work. The tools that I use — I’d love to hear about yours — I use a very simple set of tools. I always have a thesaurus open when I’m writing headlines. I just use the one that’s on my computer, but what I find is I tend to lean on certain words. I’ll write all these different headline ideas — I’m generating lots of ideas to see if I can come up with something — and I tend to reuse the same words. It starts to get boring. I crack open my thesaurus because that helps me to look up words that are a slightly different take on the same concept. I always have a thesaurus open.

I always have a blank text document open. I just write. I just write headlines. I write 10 headlines, 20 headlines, sometimes 30, 40, and 50 headlines. Then what I’ll do, is I start to bold the ones that look good. I start to make them look like a headline because I bold them. That helps me to eliminate them. Sometimes you take a word from one and you add it into another. Eventually I go through that process and I come out with some kind of a winner. You and I have some online tools, but I want to hear, do you use any tools that are different, or do you do anything different?

Stefanie Flaxman: No. My process is really similar to yours. I think it’s important to note, just write down every idea, even if it’s one word different from the last one that you wrote. Having them all mapped out is how you get to … No one’s going to see that, but it helps the process. It’s all about the process of fine-tuning and finding your best solution when you’re looking for a headline. Yeah, mine is really similar. I love pen and paper, so I will often … I’ll do that in a blank Google doc. I’m a fan of Google docs.

Yeah, my process sounds very similar to yours. The only thing different is I have lots of notebooks where I might start writing them out. Sometimes I like the way it feels to write them out, where I can see something in my own handwriting that sometimes I don’t recognize on a computer, or I’m waking up in the middle of the night for it and I don’t want to open my computer. No, very similar.

There was a comment in a blog post on Copyblogger. It was an infographic we did called Explore the Content Editor Cosmos. The headline was longer than that, but that’s enough for anyone who’s listening who wants to go look it up. The first point in the infographic was about headlines, but there was a comment in that post about, “What do you do when you’re stuck for the right word?” That’s exactly what I said. Write out every idea that you have, no matter if you think it’s dumb or silly or it won’t work. Just having it out there for you to look at is all part of the process.

Pamela Wilson: Okay, so let’s talk about tools. One of the tools that we want to share with people that we’ve been using lately actually forces you to do that. It forces you to write a lot of headlines. We discovered this tool because Demian Farnworth put together a post for Copyblogger and he mentioned this tool. He mentioned the next one we’re going to share as well. The first one is the CoSchedule headline analyzer tool. What I love about this tool is that it’s almost like a gamification of the headline writing process.

You write a headline, you plug it in, and you hit return. It basically analyzes your headline using a variety of different concepts that make a headline better and stronger. How long is it? What is the makeup of the words you’ve used? The general concept. It’s looking at all of these different things, and then it gives you a grade. Then it’s like, “I want to get a higher grade, so I’m going to keep writing headlines until I get one that gets the highest grade I can possibly get.” It’s amazing. We’ve had so much fun using that tool.

Then there’s this second tool that we also use to double-check the quality of the headline — the emotional quality. It’s the Advanced Marketing Institute Emotional Marketing Value Headline Analyzer. It’s a super long name.

Stefanie Flaxman: It’s a really long name.

Pamela Wilson: We will put all the links in the show notes for it this episode, but that one is great. What I tend to do is I’ll come up with something I’m happy with on the CoSchedule tool, and then I’ll take it over to this Advanced Marketing Institute Emotional Marketing Value Headline Analyzer and then I test that. It will tell you, “Compared to talented professional copywriters, your headline ranks this.” You can see — if it’s a boring headline it’s not going to get a very large percentage. They do theirs with a percentage grade. If it is a good one it will get a high number. It’s another way to gamify this headline writing system. But honestly, even if you don’t use either of those tools, what they do so well is they force you to keep coming up with headline ideas. That’s the trick behind headlines, is to come up with a bunch of them until you finally get a good one.

I don’t know about you, Stefanie, but what I find is when I start writing headlines, my first ideas are terrible. They’re really cliché. Any creative work I do, even artwork that I do or design work, my first ideas tend to be the most obvious clichés that are at the surface of your brain. I always feel like you have to get those ideas out of your system. You have to unplug your brain and get the good ideas. They’re more at the back, they’re hiding. But you have to unplug your brain and get the stupid stuff out first so that you can get to the good stuff that’s behind. To me, that’s what these tools do, they just give you a place where you can get the dumb stuff out of the way first. Then you can get to the good stuff, which is a little more hidden, maybe.

Stefanie Flaxman: Yeah. Oh, I think I rarely use my first idea for a headline, but it helps shape what you’re writing, which goes back to what we were talking about earlier. I would joke, I’d be like, “Okay, this article is about how to edit.” That is so vague and not good and boring. But if I wrote that down, say I was writing an article about editing and I just wrote, “How to edit.” If that was my first idea, I would just keep fleshing them out until I fine-tune, “Well, what am I really talking about? Who am I speaking to who would benefit from that?” I keep asking myself those questions and fleshing out more ideas. That silly first idea, “How to edit,” really is the base of what ends up turning into the more accurate headline that comes down the line.

I was not interested in those tools when we first discovered them from Demian’s article. I came around. At first, I was like, “I don’t want an algorithm telling me how good a headline is or not.” I’m very human. Humans have a gut feeling, and humans have all of their knowledge. I would rather not look at a tool. The reason why I came around is because one of the reasons that you just mentioned, Pamela, how it forces you to write a lot of headlines, which is just beneficial. Even if you don’t like an algorithm judging your headline for you.

Also, with tools, you can’t get carried away with them doing all the work for you or thinking that they’re going to solve your problem, but having a point of reference. It’s almost like those questions that I talked about, “Who am I writing for and how do I help them?” Those answers aren’t going to go directly in the headline, but when you have that as a reference point, “Does my article and my headline answer those questions clearly? Do I need to fine-tune what I’m writing?” The tools are very similar in a way.

It gives you another opinion. It forces you to work a little bit harder if you don’t like your score. Pamela and I are — I just mentioned you, but I’m talking to you. We, I could say we. We have lots of conversations, but sometimes if you’re creating content you don’t have someone to bounce ideas off of the way that we do. Having these tools are kind of like your co-worker.

Pamela Wilson: Yes, It’s like having another opinion. Both of those pages have lots of headline tips on them if you’re feeling stuck, and you’re not remembering what you need to be taking into account when you write a headline. They’re just good pages to spend time on because they do have reminders about what really works. Now, I have to tell people. I could not have gotten to a point that I could even use those tools if I had not studied from cover to cover the Magnetic Headlines ebook that we give away free on My Copyblogger. I will put a huge link to that in the show notes. That is really the starting point.

If you have not read and absorbed every word in that book, I would highly recommend that you start there before you try using any tools or even before you try generating lots of headline ideas. That ebook has incredibly solid guidance on what makes a good headline, and it has lots of ideas. Ideas that you can use to plug your headline concepts into and see what they do when you use the basic structures that are in that ebook. Magnetic Headlines, I highly recommend that. I’ll put a link in the show notes, but you can find it on It’s some of the free content that we give to anyone who registers on that site. That is a great place to start.

How You’ll Know When You’ve Hit on a Headline Idea That Works

Pamela Wilson: You talked about the human element and knowing when a headline is good. How do you know? What is it that tells you that a headline is going to work? Let’s just put all these tools aside and talk about, what is that human feeling in your gut that tells you, “Oh, this headline’s a good one”?

Stefanie Flaxman: Oh, wow, what a big question. Again, I go back to those questions. I want to make sure … I always say, “Lead with the most important information, lead with the benefit.” That’s in writing sentences, paragraphs. It applies to headlines too, I feel like. When I’m reading headlines on, say Twitter, if there’s a benefit for what I’m looking for in a headline, I’m going to click. I love when I fall for a headline because it promises something that I want to know the answer to. I keep that in mind when fine-tuning headlines or even writing my own headlines if it’s something that I’ve written — leading with the benefit.

I don’t want to say there’s a formula. I’m anti-formula. What’s great about the Magnetic Headlines ebook — just to go back for a second — you can absorb all that knowledge in that ebook that helps give you your own feeling for what’s going to work and what’s not going to work. If you know your audience, that is something to keep in mind as well. It all starts with the audience and who you’re speaking to. I think being specific and having a benefit for who you’re talking to in the headline is going to produce that juicy headline where someone goes, “Oh my gosh, I need to know the answer to that. That’s exactly what I’m trying to figure out.”

Pamela Wilson: Exactly, right. I think that feeling of, “I need to know the answer to that,” happens when your headline creates curiosity. You are promising a benefit. You’re making a big promise. The other thing to keep in mind is you don’t want to deliver on the promise right in the headline, because the idea is that the delivery happens in the content, not in the headline.

I’ll give you an example. You know I’m writing a book about content marketing. I’ll give you an example from the book. A headline that says, “3 simple strategies to earn your new kitten’s unending devotion,” is always going to get a lot more clicks than a headline that says, “Make your new kitten love you with good food, fresh water, and a clean litter box,” because you’re delivering the benefit right in the headline. You want to avoid doing that.

You want to promise a benefit without necessarily delivering how that benefit is going to happen, because that’s the leap that people will take. That is what will make them click. You’re saying, “Oh, I want my kitten to give me unending devotion,” because what cat gives any human unending devotion? It’s like this really juicy promise that you can’t resist. I think when you write headlines like that — keeping in mind that you’re not necessarily delivering the benefit, but you are promising it — those are the ones that get the clicks.

Stefanie Flaxman: I love that example. It’s so perfect. If you’ve delivered the benefit in the headline, why would they click? It’s giving away the farm.

Pamela Wilson: Right.

Stefanie Flaxman: Do people still say that? Is that something that people say?

Pamela Wilson: Yeah, I think so. I think so.

Stefanie Flaxman: I feel like I say that too much. It’s very cliché. Don’t write that in a headline. No, I love that example. Great, great distinction from what I said. Definitely.

Pamela Wilson: Oh, great. I want to thank you so much for being here for this episode. You and I geek out on headlines all the time, but I’m proud of the headlines we’ve come up with for our Copyblogger content. In some cases, I think we’ve really transformed the content by coming up with these amazing headlines. It’s one of the most fun parts of the job that you and I work on together. I just love it. I’m really happy that you could join me for this episode.

Stefanie Flaxman: Me too. Thank you for having me, and thank you everyone for listening. I hope you got some good tips for your own content.

Pamela Wilson: I’m sure everyone did. I will be back next week with more content marketing information for you. Every episode of Copyblogger FM has show notes, and this one has a lot of links to the tools and the resources that Stefanie and I mentioned. You can find them all at Copyblogger FM. Thank you, as always, for your time and attention. Now go forth and be excellent. See you next time.