Here are some of the best questions for a SaaS customer survey about free trial experience, plus smart tips for designing them. You can quickly generate a survey like this with Specific and start collecting actionable feedback in seconds.
Best open-ended questions for SaaS customer free trial surveys
Open-ended questions let customers share stories and give honest, nuanced feedback. They’re fantastic when you want to uncover “why” behind actions or hear pain points you didn't expect. That’s especially powerful in SaaS, where conversion rates from free trials can vary widely depending on the experience you create—like how opt-in free trials have an average free trial to paid conversion rate of 18.2%, versus 48.8% for opt-out models [1].
Here are 10 of our favorite open-ended questions to ask after a free trial:
What was your primary goal in signing up for our free trial?
Can you describe any challenges or frustrations you encountered during the trial?
Which features did you find most valuable, and why?
Was there anything missing that you expected to find?
How does our product compare to others you have tried during a free trial?
What would have made your experience better?
Were you able to accomplish what you wanted during your free trial? If not, what stopped you?
Tell us about any moments when you felt excited or disappointed while using our product.
How clear were our onboarding instructions and in-app guidance?
If you didn’t upgrade, what was the main reason?
Best single-select multiple-choice questions for free trial surveys
Sometimes you need structured data—to quantify results, spot trends, or simply kick off a conversation. Single-select multiple-choice questions make this easy: respondents pick an option, then you can go deeper with a follow-up.
Question: How easy was it to get started with our product?
Very easy
Somewhat easy
Neutral
Somewhat difficult
Very difficult
Question: Which feature did you use most during your free trial?
Dashboard/Reporting
Integrations
Collaboration tools
Automation
Other
Question: What best describes why you didn’t upgrade after the trial?
Too expensive
Lack of needed features
Complicated to use
Already using a competitor
Other
When to follow up with “why?” We usually ask “why?” after any choice that signals a problem or a particularly strong opinion. For instance, if someone chooses “Very difficult” or “Complicated to use,” a follow-up (“Can you tell us what made it difficult?”) unlocks specific, actionable details.
When and why to add the “Other” choice? Some users don’t fit the typical categories. The “Other” option, followed by a prompt for specifics, reveals insights you wouldn’t get otherwise—maybe an integration you didn’t know they cared about or an unseen competitor. Those off-the-radar nuggets are often the most valuable for SaaS growth.
Should you use NPS for free trial experience?
The Net Promoter Score (NPS) question (“On a scale from 0–10, how likely are you to recommend our product to a friend or colleague?”) is a gold standard for SaaS companies—especially right after a trial. It’s a proven way to benchmark satisfaction, identify promoters or detractors, and track improvements over time. Given that SaaS products in certain industries, like CRM, achieve free trial to paid conversion rates up to 29% [3], understanding NPS during the trial phase can guide your next product moves.
If you want to get started fast, here’s a NPS survey preset for SaaS free trial customers—ready to customize and launch.
The power of follow-up questions
Follow-up questions are where you turn surface answers into deep insights. With Specific’s automated follow-up questions, the AI handles this in real time, just like a skilled researcher would.
Get clarity where respondents are vague or incomplete.
Uncover motivations behind each answer (“why did you hesitate to upgrade?”).
Collect richer, more nuanced feedback—without the time drain of emailing back and forth or manually probing every answer.
Say you get this response:
SaaS Customer: “Setup was confusing.”
AI follow-up: “Can you share which step or screen felt confusing, so we can improve it for others?”
How many follow-ups to ask? Usually, 2–3 focused follow-ups are enough to clarify or dig deeper. With Specific, you can set rules so the AI knows when to stop or can skip ahead when you have what you need—keeping things conversational, not tedious.
This makes it a conversational survey: Every exchange feels like a real chat—not an interrogation—making everyone more likely to open up.
AI-driven analysis, even for open text replies: Analyzing rich qualitative data is often the hardest part of surveys. With tools like Specific’s AI survey response analysis, sifting trends and key insights from open-ended answers is a breeze.
This automatic follow-up feature is a relatively new approach. We recommend exploring how it works: try generating a survey and see how conversation flows differently.
Crafting great SaaS free trial survey prompts for ChatGPT
AI is great at brainstorming questions. The trick is setting context. To start, you might prompt:
Suggest 10 open-ended questions for SaaS customer survey about free trial experience.
But AI does even better with more detail—describe your users, your product, and your goals:
We are a SaaS company helping small businesses manage their finances. Please suggest 10 open-ended questions that reveal barriers to upgrading from free trial to paid, focusing on ease of use, feature gaps, and onboarding.
Next, have the AI organize the raw questions:
Look at the questions and categorize them. Output categories with the questions under them.
Once you review categories (like “onboarding”, “feature satisfaction”, “pricing”), go deeper by prompting:
Generate 10 questions for categories onboarding and feature satisfaction.
This approach—categorize, then go deep—often results in sharper, more targeted surveys tailored for your SaaS product’s trial experience.
What makes a conversational survey different?
Let’s compare traditional survey building with an AI survey builder like Specific, which creates conversational surveys for SaaS customers:
Manual Surveys | AI-Generated Surveys |
|---|---|
Time-consuming to write and structure every question | Instantly generates expert-level questions using your specs or prompts |
Static—doesn’t adapt to the respondent’s answers | Conversational—asks tailored follow-ups in real time for depth |
Responses often vague, with no easy way to get context | AI clarifies, asks why, and ensures rich answers from each user |
Why use AI for SaaS customer surveys? AI survey generators save hours, craft precise and relevant questions, and make feedback feel more like a dialogue—engaging users and surfacing high-value insights. For SaaS teams, this improves both response rates and the quality of data you get, which is key given free trial conversion can be as low as 8% for some segments [2]. If you want to learn how to create a survey for SaaS free trial users, we’ve detailed the process step-by-step here.
Specific’s unique approach—best-in-class conversational survey UX—turns every survey into an opportunity. Customers feel like they’re chatting with a helpful expert, not just filling in a form. That makes a massive difference in honest feedback and conversion insights.
See this free trial experience survey example now
Get actionable insights about your SaaS free trial users—see how conversational surveys uncover hidden blockers, drive up engagement, and make analysis effortless. Start now and boost the way you collect and act on customer feedback instantly.