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Questions to Ask SaaS Trial Users (And How to Use the Answers)

There’s nearly never a bad time to ask your SaaS user’s questions to get to know them better. While it’s possible to annoy them with too many requests for feedback, you won’t have that issue if you ask the right questions.


As tempting as it can be to take a “set it and forget it” approach to your onboarding emails, marketing campaigns, product features, or brand positioning — you’re doing you and your customers a disservice if you do. User needs and perspectives change, and it’s important to be proactive about learning and growing with your community.

What should you ask your customers, though? Let’s break down five questions you can use to get to know your customers.

Where do you want you/your business to be in a year?

What do you need to do for your SaaS to be a means to a goal, and not just another tool? First, you’ll need an understanding of where users want to go. Asking them where they want their business to be in a year will show you:

  • What their definition of success is

  • How big their goals are

  • What metrics or standards they use to evaluate success

How to use the answer

Understanding what users want to achieve helps you start them off on the right path immediately. By knowing what success is to them, you can determine what features or way of using your tool will serve them.

What is holding you back from reaching your goals?

You can’t overcome what you don’t address. While this question is good for you, it may also be an eye opener for your users. Are they struggling to find time to commit to consistently working on a task? Are they unsure of what strategy to use? Do they not have buy-in from others on their team? By helping users identify what’s challenging them, you can help them overcome it.

How to use the answer

Now that you know what’s troubling users, figure out how you can best support them. If time is an issue, perhaps they could use more consistent reminders or to have tasks broken up into smaller pieces. It’s also possible that you have content on the topics they need help with.

What made you decide to sign up for a trial?

Do you know why users really sign up for your service? Sure your features and value prop play a large role, but what was the context for the decision? Whether users realize it or not, there had to be some catalyst or single tipping point proposition that made them say yes at that moment. This reason could have been negative (think of “the final straw that broke the camel’s back”) or positive (they saw a testimonial from someone they trust).

How to use the answer

You may not use the insights from this question in your onboarding strategy, but it may be able to help you land more sign ups. If you see a common pattern of catalysts, either negative or positive, you can bring those forward on your website or sales materials.

What tool do you feel most unsure about?

If there is a particular feature or tool within your product that users don’t like, you surely want to know. You can ask users what feature they use the most vs the least, and which they like the most vs the least. Were there any features they never touched, and if so, why?

How to use the answer

With these answers you can begin to decipher what features matter for different user segments, and what their feelings are about them. Pass negative feedback back to the product management team, and prioritize showcasing and educating about the features that really matter.

What do you hate about your current solution?

Here’s another question that can help you in the lead generation phase. By identifying what a person hates about their current way of doing things, you can position yourself against it.

How to use the answer

Highlight particular aspects of your service that are as far removed from the cumbersome details of a person’s current solution as possible.

Now that we’ve gone through five questions to ask SaaS free trial users (and how to use their answers), let’s address how and when to ask them. A few options include:

  • On a support call at the beginning of a trial

  • As a survey within your email sequence

  • Within your product

  • On your social media pages or community groups

Do you have any other questions you like to ask users?