The first step in increasing conversions from trial to paid customers is to get a clear picture of what your target customer is trying to accomplish with your product and why.

Let’s start with a basic question: Why did they sign up in the first place?

They saw your site, filled out a form, and started a trial, but for what purpose exactly?

It’s tempting to assume they signed up because they want to do exactly what your website copy said that your product would do.


It’s equally likely that they heard about you from a friend who is mistaken about what your product does. Or they searched for a keyword that you use, but in a different way than what they are interested in. Or they read your website copy, and it’s vague enough that they are hoping you can solve their problem (but you can’t).

So this is a critical thing to understand to really dial in your marketing messages, and also to see if the people signing up for trials seem to be consistent with who you are tryuing to attract.

But more importantly, especially for early stage businesses, asking this question can give you invaluable insights into the problems and pains of your customers. What was top of mind when they signed up? Is there a pattern of problems that seem like a better (or worse) fit with what you are doing?

Asking the right question

So how do you get this information from trial users? Do you add another field to your signup form? It’s an option, but I wouldn’t recommend adding any more friction during signup.

Instead, one quick, simple tactic is to send a welcome email with a single question.

What is the biggest thing you were hoping to improve with Product X?

You can frame it a little differently, but what you are looking for here are direct replies from people who spent some of their time looking at your website, and trusted you with their email address to start a trial.

Not everyone will reply, but if you as a founder (or senior executive) reach out personally, you’ll see a much higher response rate than something from “” or “”

Ok, now you’ve got some replies. Talk to as many of these people as you possibly can to tease out what they are trying to make better. If you have a B2B product, that usually means your customers are looking to releive a pain, or looking to increase revenue somehow.

I’ve had good luck with having a chat over email, and then sometimes inviting them to have a quick call if they are interested in having a deeper converstaion. Some of the questions I might ask for followup would be around what industry the person is in, how they have tried to solve the problem in the past (this is a very good sign if they have spent time or money on failed solutions), and what other products they have tried.

After about 10 of these conversations, you should know if you have a more focused customer base or if the signups are more distributed. If you have a wide range of customer problems, there may be an issue with how you are talking about your product in copy. Is it specific enough? Does it clearly outline the main benefit for your ideal customer?

If you have a good concentration of customer problems, you can move on to identifying what Lincoln Murphy, a prolific writer on SaaS onboarding, calls the Desired Outcome for your customer. But that’s a subject for another post.