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Copywriting Interviews

I Thought I Knew About Copywriting… Until these Experts Schooled Me

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I thought I knew copywriting like the back of my hand. Really, I did. And to be fair, I’ve gotten some pretty sweet clickthrough rates on ad copy and conversion rates on landing pages. But after conducting the following interviews with some experts who just write copy, I realized that I’ve got so much more to learn.

For example, research is every copywriter’s secret weapon, yet I was missing some supremely easy sources for insight into audiences’ emotions. And some of the headline and swipe file advice below is just, well, priceless.

So if you would like a backstage pass to see how some of today’s best copywriters approach key parts of their work, read on. You’ll get to see the patterns in their methods. If you adapt their methods to your work, you’ll quickly improve your copy and increase your conversions.

I spoke to four experts for this interview:

Josh Garofalo of Sway Copy
Joel Klettke of Business Casual Copywriting
Cassie McBlane of WME Group
Stephen Altrogge of Copy Swagger

and yours truly (the interviewer) is Gab Goldenberg of

Note: In each section, I asked questions that overlapped with one another, so I told the respondents that they didn’t have to answer each question separately. That’s why you won’t see each respondent answering every question.

Research for Copywriting

How do you research your audience?

Joel: Whenever possible, I try to get clients to do a survey of customers with questions that ask them about their buyers’ journey. I review testimonials, case studies and online conversations, always looking for soundbites I can nab or angles I need to consider. I look at competitor testimonials too – know the enemy, so to speak.

Copywriting expert Josh Garofalo
Josh Garofalo of Sway Copy

Josh: Research is the foundation of any copy that I write. I believe in it so much that I refuse to work with clients that want to save money by skipping this step. The copy that I produce myself or by brainstorming with the marketing team is weak when compared to what I can get straight from the prospect.

My favourite technique for capturing the voice of the customer is message mining (surprise, I learned this from Joanna, too). It’s as simple as finding where my client’s prospects are talking about what my client does, going through their comments, and recording common terms, phrases that stand out, what people say they want, and the pains they are experiencing.

Here’s an example of message mining for an email marketing SaaS startup that needed an email course written and a landing page created to capture leads for it:

1) Go to and search “email marketing.” I’m looking for a book with a decent number of reviews. I’ve got 62 reviews to read through on this book alone.

2) Check out the table of contents and take note of topics and terminology. If this book has a good overall rating, looking at the topics and terms covered can inform the topics and terms I should include in my email marketing course. For this specific use case, finding a popular email marketing course on Udemy can also be great inspiration.

3) Read through the comments to find phrases that stand out, tell you what they want, and express pain and frustration.

4) Finally, aggregate this information from this and other resources until I feel like I have enough prospect input to inform my copy. At the very least, I’d want enough information to put together the surveys/microsurveys/interview questions that will uncover the message that will resonate with my ideal prospects.

At the end of this process, I’ll feel like I’ve had chatted with dozens of prospects. The bonus is that I didn’t have to schedule interviews, pay anyone, or worry that they were trying to say the “right things.”

Cassie: Before completing any copywriting or SEO work, we thoroughly research our clients’ target market and audience by exploring forums for current trending questions from the market, as well as looking at social media platforms to find out the latest conversations. This is a great way to find out what’s being talked about by the target market, and really micro-target their interests. Twitter’s advanced search function works great for this. In more simpler cases, we contact the client to speak with them one-on-one to help us define and capture exactly what their audience is all about. This is often relayed through interviews.

Stephen: Most of my copywriting is done for clients. My primary research consists of spending a lot of time talking to the client so that I fully understand what they are trying to accomplish.

Do you interview any audience members? If so, what do you discuss?

Joel: I’ve got a list of questions I ask. It’s never yes/no if I can avoid it – always an attempt to get them to explain their experience or share their story. What did they try before this solution? What didn’t they like about it? What’s been the best part of using this service or product? Where could they improve? What were they worried about before signing on? Where do they fit in the company hierarchy? It’s more organized than that, but basically, I’m trying to get them to tell me a story. Stories are more useful than data points and yes/no binary answers.

[tweetthis](On audience interviews) It’s never yes/no. I always attempt to get them to explain their experience[/tweetthis]

Stephen: I don’t normally interview anyone other than the client.

If not, what tools or other methods do you use? What would you recommend to others?

Joel: Like I said – I check out online conversations and eavesdrop all over the web. You can’t skip primary, qualitative info-gathering and expect to convert well. Your assumptions and biases will almost always remove you a few steps from the truth of how your customers think, and what they value in your offering.

Cassie: If you’re looking to delve deeper into social media, tools like BuzzSumo, Hashtagify and Simply Measured can shed a lot of light on audience behaviour and interaction. These tools also work great for other types of copy. If you’re looking for the most engaging topics to cover, even simple platforms like Reddit can do you a huge favour.

Swipe files

What use – if any – do you make of swipe files?

Josh: I don’t usually start a project with swipe files. Instead, I use them when I’ve hit a wall to help me get something on the page. I’ll also use swipe files to compare copy I’ve written to copy that has already been written, published, tested, and validated. The goal isn’t to ensure that my copy follows a formula perfectly — it’s to check that my copy is in the same ballpark as the kind of copy that has worked repeatedly over the years.

Copywriting Expert Joel
Joel Klettke of Business Casual Copywriting

Joel: Whenever I feel stuck on some client work – or whenever I find myself reading something I’m really impressed by, I try to keep a growing file I can turn to for ideas. As a writer, you get too used to writing in your own patterns; swipe files act like combo breakers, pushing you to try new things.

Stephen: I realize that this is probably terrible practice, but I don’t really use swipe files. More than anything, I just try to stay “up” on what a lot of different people are doing – people like Joanna Wiebe, Ash Ambirge, etc. Theoretically, I would spend more time creating swipe files, but theoretically I should also be less busy.

Cassie: We don’t use swipe files.

If you use swipe files, how is yours organized?

Joel: I try to keep things organized by industry or content type, but if I’m honest, my file is pretty messy.

Josh: For swipe files, Joanna Wiebe’s recent post, The Ultimate Guide to No-Pain Copywriting (or, Every Copywriting Formula Ever), takes care of 80% of my swipe file needs. It’s a gigantic resource with a super convenient table of contents that makes finding exactly what I need quick and easy. Headlines, subheadlines, short and long-form sales copy — it’s all there.

I keep a separate swipe file for email campaigns. Setting this up is as easy as signing up for the lists of people and companies that send out effective email campaigns and creating filters to keep campaigns separate.

Where do you collect ideas from for the file?

Joel: All over the place. Websites, blog posts from people I look up to (like Copy Hackers or WiderFunnel), ads I come across in magazines – wherever there’s copy. Great copy is everywhere, you just have to watch for it.

Josh: I sign up for 4 kinds of lists:

People that write emails that appeal to me. (freelance copywriter)

Paul Jarvis
Brennan Dunn
Joanna Wiebe
Brian Dean

People/companies that write emails that appeal to my ideal client and their competition. (SaaS companies)

SaaS Weekly

People/companies that just write effective emails, period.

Pat Flynn
Noah Kagan (OkDork)

Email marketing companies (because they should know how to do this better than anyone.)


Coming up with Headlines

How do you write your headlines?

Josh: Again, reference Joanna’s copywriting formula post. There are dozens of headline formulas with tested examples for a variety of markets.

Aside from that, I also reference chapters on headlines from copywriting/advertising classics. For example, chapters 2-5 in “Tested Advertising Methods” by John Caples is loaded with headline formulas backed by real and tested examples that worked. Chapters 3-7 in “Scientific Advertising” by Claude C. Hopkins is also filled with accessible gems. And, while not yet a classic, Joanna’s “Headlines, Subheads & Value Propositions” is overflowing with headline copy wisdom.

I don’t go out of my way to search the internet for headlines that look good because, well, I don’t know how they are actually performing. What looks good doesn’t always perform. I will take note of headlines from sites such as Crazy Egg, Pagewiz, KISSmetrics etc. because I know they test religiously.

[tweetthis]I don’t search the internet for headlines because I don’t know how they are actually performing[/tweetthis]

When I’ve got my headline copywriting juices flowing, I like to get at least 10 headlines written. To avoid what Barry Schwartz calls “The Paradox of Choice”, I present clients with no more than two or three standout headlines. I’m also careful to only present headlines that I’ll be happy with if chosen.

At the very least, I like to check the following boxes when writing headlines/subheadlines:

  • Match visitor expectations (based on where they are coming from)
  • Capture visitor’s attention (what they are looking for)
  • Language is more clear than clever (sounds like something a non-poet might say)
  • Gets to the foundation of what the visitor wants (no extra words that slows consumption)
  • Demonstrates the presence of something valuable to my visitor (a solution to a problem)
  • Get specific whenever possible (data, numbers, etc.)

This is straight out of Joanna’s book on conversion copywriting.

Copywriting Expert Cassie McBlane
Cassie McBlane of WME Group

Cassie: We’re big believers in the keep it short, sweet and simple rule, but also like to get a bit witty where we can. Headlines with numbers – e.g. ‘The Top 5 Ways to…” work most effectively for our discussions, whereas tongue-in-cheek headlines can also drive traffic. Depending on the context and nature of the blog/content, we like to get a bit creative (we also love a good pun). You can see this blog on our website for more.

Joel: It totally depends on the context of the page. Before I get going, I list out the questions and pain points a customer might have – everything from “Who is this company?” to “Why should I care? Then, I try to give every component of the page a job to do – a question to answer, prioritized to how early on I think a lead will ask it or how important it is that the question gets answered early. Usually, headlines serve dual purposes for me – clarifying the offer, and stating the unique value proposition. Then I use a sub-head to help disambiguate the offer and add a little more detail.

Here’s an example of the work I did for Webzio, where I gave the headline a couple jobs:

  • Clarify the offer (Answer the “What is this?” with “We build, optimize and promote…)
  • Offer up the primary benefit (Answer the “Why should I care?” with “You’ll make money.”)

Then, I used a sub-header of sorts to clarify things even further:

  • I added details on the services (Now, a lead knows they market, design, code)
  • I added more desirable outcomes (Increased leads, improved experience, better rankings)

By the end of this section, a lead knows what the company does and knows the kind of outcomes they should expect – outcomes aligned with what people hiring a digital marketing agency are looking for.

Stephen: Before I do any headline writing, I really want to understand exactly what I’m trying to convince people to do. The headline is the first impression. When I understand what people really want and what I’m really trying to accomplish, then I can actually write a good headline. So I really spend a lot of time trying to get clear on the primary goal of the copywriting project before I actually get into writing headlines.

How many headlines do you write before picking 1-2 to test?

Cassie: In the majority of cases we choose to create a number of headlines at the outset, and then work through the rest of the copy before we choose one final headline. This helps us to get an idea of exactly the tone of voice and purpose of the content as we go, allowing us to make an accurate and effective decision in the final stages.

Joel: It changes all the time. Sometimes I’ll write 20 or more variations before I find one I really like. But I think it’s important to note that I don’t automatically choose to go headline testing. I try to pick one to serve as a baseline, and until I know the headline is the problem, I leave it alone to collect data. It’s fruitless to just generate a whole bunch of headlines off the bat and start testing there – how will you ever know if the headline was an issue – or a positive force?

[tweetthis]Sometimes I’ll write 20 or more headline variations before I find one I really like.[/tweetthis]

Stephen: However many it takes until I feel really satisfied. I push until it’s sufficiently clear, sufficiently urgent, and sufficiently specific.

How different is each one from the next?

Joel: Depends. I follow formulas when I get stuck, depending on the situation. They can vary a lot, but since I’ve given the headline a job, they’re all in the same vein.

Stephen: They usually improve by increments, a couple words at a time. Not a huge difference between each headline.

Body of the copy

How do you write your lead sentences, captions and other copy elements?

Joel: The same framework – everything has a job.
I always try to draw from the research I’ve done before I began; reading testimonials, case studies, qualitative surveys and trying to write as much of the page in the customers’ own words.
I prioritize the page based on that framework of questions I think the client needs answered, and just move from section to section answering them in as poignant a way as I can.

Copywriting Expert - Stephen Altrogge
Stephen Altrogge of Copy Swagger

Stephen: My primary goal is for every section to PUSH the reader down to the next section until they finally arrive at the CTA. So every part of the copy has to pass the “push” test. Does it push the reader down? Are they compelled to keep going? If not, then I need to go back and rewrite something.

Josh: I’m not going to comment here because there are too many variables and too little space. What goes into the body copy is very specific to the client, their audience, and their goals.

Cassie: We have a big pet hate of tacky questions at the start of content. These often come off as amateur in quality and “salesy”. Our team of writers focus on using a bit of wit, humour and professionalism to craft compelling copy that still puts the brand message in the spotlight. Sometimes, lead sentences or main headings may be coached and discussed by the writing team, or simply devised on the spot.

Do you have some suggestions for creating strong, dynamic copy that weren’t brought up by these experts? We’d love to hear your thoughts in the comments section.

Landing Pages Designer

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