Here are some of the best questions for a Free Trial Users survey about conversion barriers, plus practical tips on designing them. If you need to build a survey like this, Specific lets you generate one in seconds using AI, fully tailored to your need.
Best open-ended questions for understanding conversion barriers
Open-ended questions help us discover the real reasons why users didn't become paying customers. We use them when we want rich, nuanced answers—insights that multiple-choice questions simply can’t provide. Open-ended questions are especially powerful at the end of the trial period, where motivations are varied and complex.
Here are the 10 best open-ended questions we ask:
What made you decide not to upgrade to a paid plan after your free trial?
Were there any moments during your trial that made you hesitate to continue?
What features or improvements would have convinced you to subscribe?
How did our product compare to your expectations before starting the trial?
Were you looking for something specific that you didn’t find in our product?
How was your overall experience using our product during the trial?
If you considered upgrading but didn’t, what influenced your final decision?
Is there anything that frustrated you or slowed you down during your trial?
Can you describe a specific moment when you realized you wouldn’t upgrade?
What’s the one thing stopping you from becoming a paying user today?
These open-ended questions often reveal barriers that SaaS teams may overlook—for example, interface confusion, pricing uncertainties, or lack of onboarding support. That’s essential because over 55% of SaaS teams score their free-to-paid conversion ability at less than 5 out of 10, highlighting just how tough it is to move free users to paid plans. [3]
Best single-select multiple-choice questions to quantify barriers
We use single-select multiple-choice questions when we want to quickly spot trends or quantify the biggest hurdles. They're perfect for validating the most common conversion barriers, or as an “icebreaker” before digging in with follow-up questions. Sometimes, picking from a list is simply easier for overwhelmed users—especially if you follow up for clarity after.
Question: What was the main reason you didn't upgrade to a paid plan?
The price felt too high
I didn’t see enough value
I found the product difficult to use
I’m still evaluating alternatives
Other
Question: How would you rate the onboarding experience during your trial?
Very easy to get started
Somewhat easy
Somewhat hard
Very hard
Question: Which of these best describes your main barrier to upgrading?
Unclear pricing
Lack of needed features
Security or compliance concerns
Decision is outside my control
Other
When to follow up with "why?" Sometimes answers to single-select questions don’t tell us why. Following up with a simple “Could you tell us more about why you chose that answer?” turns a closed response into a thoughtful conversation. For example, if someone selects “I didn’t see enough value,” ask: “Can you share a specific feature or workflow you found lacking?” This uncovers context we’d never get from checkboxes alone.
When and why to add the "Other" choice? Always include “Other” if you’re listing common barriers. The follow-up lets users describe unique challenges you didn’t anticipate. Many times, new patterns emerge—like unexpected technical blockers or concerns about contract terms—simply because you left room for those voices.
Should you use an NPS question for free trial user conversion surveys?
NPS (Net Promoter Score) isn’t just for measuring satisfaction after someone pays—it’s a powerful tool for understanding sentiment during the trial period, too. Asking, “How likely are you to recommend our product to a colleague or friend?” gives you a high-level sense of whether users see value, even if they decide not to convert. It also helps segment your feedback: For example, detractors may have hit stumbling blocks, while promoters might hesitate for price or organizational reasons. Running an NPS-style survey as part of your trial-ending questions can clarify which conversion barriers matter most for users who like your product (versus those who don’t).
Given many SaaS teams see conversion rates as low as 21.9%–29% [1], understanding promoter (and non-promoter) behaviors during trial can be a game changer.
The power of follow-up questions
Conversational surveys unlock richer insights by turning answers into dialogue. Our feature—automated AI-powered followup questions—lets the survey itself dig deeper, just like a skilled interviewer. This means when a Free Trial User gives a short or vague answer, the AI agent can clarify; if they’re passionate or frustrated, it can probe for detail right away.
Free Trial User: “It was just too complicated.”
AI follow-up: “Could you share which part of the product felt complicated or where you got stuck?”
Without this, we end up with unclear replies—leading to guesswork or needing to send email follow-ups (which rarely get answered). Automated followups save teams hours and boost data quality, making the survey feel like a real conversation.
How many followups to ask? Usually, 2–3 follow-up questions are enough. You don’t want fatigue, but you do want context. Specific lets you set this per question and automatically skip to the next topic once you’ve captured what’s needed.
This makes it a conversational survey—the respondent feels heard, not interrogated.
AI survey response analysis is painless too. There’s a lot of unstructured text, but AI makes it easy to analyze responses from free trial users surveys instantly—finding themes, summarizing sentiment, and extracting action items.
This is a new concept, and we encourage you to try generating a survey just to see how much smarter and more natural followup questions can make the process.
How to prompt AI (like ChatGPT) to create your custom survey questions
One way to develop great survey content is to use AI directly. If you’re using ChatGPT or any GPT-based tools, here’s a simple process:
Start with a direct prompt to get initial question ideas:
Suggest 10 open-ended questions for Free Trial Users survey about Conversion Barriers.
The quality of the output goes up dramatically when you give context about your company, product, audience, and goals. Example:
I'm a product manager for a SaaS tool designed for small businesses. I want to identify the main reasons free trial users don't upgrade to paid. What open-ended questions should I ask to uncover barriers around onboarding, feature gaps, pricing, and value perception?
Once you have a list, prompt the AI to organize them into logical groups for clarity:
Look at the questions and categorize them. Output categories with the questions under them.
Then, select the categories you most want to address and ask the AI to dive deeper:
Generate 10 open-ended questions focused on “onboarding experience,” “feature gaps,” and “pricing/value perception.”
This approach makes sure your survey covers every angle—and with tools like Specific’s AI survey generator, you can go from brainstorm to launch in minutes.
What is a conversational survey—and why use AI to build one?
Conversational surveys feel like natural chats, not rigid forms. Instead of presenting a static list of questions, you interact with users in real time—responding, clarifying, and reacting based on what they share. This format increases engagement and delivers richer insights by following up on ambiguous or interesting answers automatically.
Building one manually is possible, but it’s tedious. You’d need to script every possible follow-up, think through branching, and manage the logic for each reply. That’s where an AI survey builder shines: you describe your goals and context, and AI creates a dynamic, intelligent survey flow—no complex scripting required.
Manual Surveys | AI-Generated Surveys |
|---|---|
Static; all users see the same questions | Adapts to responses in real time with smart follow-ups |
Requires hours of manual design & testing | Ready in minutes; just describe your goal |
Hard to analyze messy, unstructured answers | AI summarizes, tags, and extracts key insights instantly |
Low response rates; feels impersonal | Feels like a real conversation; higher engagement |
Why use AI for free trial user surveys? Because these users face a maze of choices and blockers—in moments, not months. Gathering real-time, contextual feedback makes it easier to pinpoint conversion barriers and act before their trial ends. Specific’s AI survey example flows are proof: adaptive, intuitive, and ready for complex SaaS feedback. For step-by-step advice, see our guide on how to create a survey for free trial users.
Specific delivers the best-in-class user experience for conversational surveys—making the response process smoother for both creators and the people taking your survey.
See this conversion barriers survey example now
Want user feedback that’s deep, actionable, and delightfully easy to collect? Start your own conversational survey and discover what’s really holding free trial users back from upgrading. See what instant, AI-powered follow-ups and rich, usable insights can do for your SaaS growth.