How to improve your free trial emails in 15 minutes

How to improve your free trial emails in 15 minutes

14 minutes, 37 seconds, actually.

Because after 9,821 hours of practice, that’s all it takes for me to decide whether your email campaign is helping or hurting your trial-to-paid conversion rate.

Yes, I realize I sound like a used car salesman.

But here’s the reality. Your trial user probably spent 21 seconds reading your first onboarding email.


Email is your only shot to show them how much pain they’ll be in if they don’t choose your product…and you’ve only got a little less than 3 minutes to prove it to them.

And it all starts with a framework that I borrowed from the user experience world.

How to Apply UX Research to Email

My email campaign review service helps a startup founder decide whether rewriting their emails will reduce their churn rate.

They don’t want custom work. They don’t need to talk about strategy.

What they need is to know exactly what they’re screwing up on so they can convert more of the people coming in.

By doing this, I give you a sample of what I would fix, based on mistakes I’ve seen made by other SaaS companies.

I always spend 15 minutes reviewing a campaign before I start any client project. And it’s based on the concept of needfinding.

So What Exactly is Needfinding?

In my consulting firm, we define needfinding as:

Discovering what the problem space of the project, who the users will be, and what requirements they would like to see in the end project.

In human speak, needfinding is finding the right scope of work.

And needfinding is just 1 of the 4 steps in what Georgia Tech’s User Experience Design course calls the design life cycle.


In Other Words, Needfinding is a Fancy Term for Research

If you’re rewriting a homepage, a landing page, or some emails, you know better than to start without doing any research.

To begin, you might consider…

  • Interviewing customers
  • Observing users interacting with your product
  • Designing a survey

But even if you’re well-funded, there’s nothing worse than hiring someone to get a task off your to-do list — then they spend weeks talking to customers and not producing a damn thing.

The only organization that lets you get away with that is your local university.

If you are going to pay a premium for a consultant, you want them to get up to speed fast…and the outcome to be good.

Why Good Research Methods can be Fast & Cheap

So I collected some of the needfinding / research methods I knew about, and then ranked them by some categories like cost and ease of learning.

For any given project, you may choose a handful of methods.

But if you look closely, there’s one that happens to be cheap, robust, flexible, convincing, AND easy to learn…

It’s called a Think Aloud.

Here’s what the Guru of Web Page Usability Says about Think Alouds

Think Alouds are Jakob Nielsen’s tool of choice when working on projects for the world-renowned Nielson Norman group:

“Thinking aloud may be the single most valuable usability engineering method.” I wrote this in my 1993 book, Usability Engineering, and I stand by this assessment today. The fact that the same method has remained #1 for 19 years is a good indication of the longevity of usability methods.

To do a Think Aloud, ask your users to use your system “while continuously thinking out loud — that is, simply verbalizing their thoughts as they move through the user interface.

It’s more or less the premise behind User Testing & UsabilityHub. Here’s why a think aloud so effective to a product owner:

“[Think Alouds serve] as a window on the soul, letting you discover what users really think about your design. In particular, you hear their misconceptions, which usually turn into actionable redesign recommendations…even better, you usually learn why users guess wrong about some parts of the UI and why they find others easy to use.”

So now we know: If you use Think Alouds to review your email campaigns, you start to understand what your users believe about your SaaS product…and whether it’s worth it to go for “the click.”

Here are 2 reasons a think aloud will help you see what’s going on with your email campaign.

1. Your workflow isn’t working the way you expect it to

The best way to review an email campaign is not in a Google Doc…

And a workflow diagram never helps.

So I do the next best thing: I opt into the campaign myself. And I make sure to record my screen while reading through the emails.

For more about CrankWheel, keep scrolling to find my sample review of their emails.

By reviewing emails this way, I’ve found edge cases that my client didn’t even know about. (Like figuring out some of their users were getting subject lines A & B.)

So now we know: A video screen recorder (I like Loom) is the best way to see what’s happening after a prospect opts into your email campaign.

Yet, there’s another reason the think aloud is useful when reviewing emails…

2. You probably didn’t read your emails out loud

I’ve found the strangest things when reading emails out loud.

Typos. Missing words. Awkward phrasing.

99% of the time, I don’t care about that stuff. That’s easily fixed.

I’m more concerned about what your customer thinks overall.

So instead, I turn on my microphone to have a conversation with myself, using two different personas.

The first persona is a trial user who signed up for the first time.

The second persona is an email consultant.


You may think I’m crazy (literally), but it’s actually an 83-year-old therapy technique they call dialogue chairsAccording to Leslie S. Greenberg, it’s defined as:

“Encouraging a client to dialogue between two aspects of the self, one aspect expressed while sitting in one chair and the other expressed while sitting in the other chair, switching as needed from one chair to the other.”

You don’t have to physically switch chairs to utilize the methods, but the idea is to acknowledge the two personalities inside your head.

So to demonstrate, my trial user persona might say,

“Hmm. That subject line intrigues me. I’m going to open this email.”

In contrast, my email expert persona might say,

“This subject line utilizes curiosity to prompt the user to open it. It works initially, but loses effectiveness when it’s used throughout a 7-part onboarding sequence.”

See the difference?

What Happens During a 15-minute Email Campaign Review

To demonstrate how this works, I did a 15-minute review for CrankWheel, after their founder, Jói Sigurdsson included an article I wrote in his newsletter.

After the end of the review, I made 3 recommendations to Jói…

1. Edit the cadence of their transactional emails vs. onboarding emails, if possible

2. Be very specific about who is the ideal customer of CrankWheel. In this case, it’s teams with a dedicated customer experience team during normal business hours

3. Figure out the 1 step a trial user needs to get the most ROI out of the tool…and spend your time trying to get them to do that

Here’s the 15-minute review

Want a Quick Recap on Using Think Alouds for Email?

So if you’re scratching your head and trying to figure out how to move the needle on your trial-to-paid conversion rate and want to fix it fast…try doing a think aloud on your onboarding email campaign.

Here’s how it works…

1. Opt into your email campaign through your website

2. Record your screen as you sort through the emails in your inbox (I like Loom)

3. Read your emails out loud, alternating between your customer & yourself

And make sure to let me know if you can do it in less than 15 minutes.

~Sophia :)

P.S. Don't have the time to do it yourself? Check out the email campaign review to see if you're a good fit. 

Does give me total control of my money? I put their emails to the test

Does give me total control of my money? I put their emails to the test