Best questions for free trial users survey about activation barriers

Here are some of the best questions for a Free Trial Users survey about activation barriers, plus tips for designing them. You can generate a tailored conversational survey with Specific in seconds, so you can go deep fast and unlock what’s really blocking user activation.

The best open-ended questions for a Free Trial Users survey about activation barriers

Open-ended questions help you uncover the “why” behind user actions or hesitation. They’re perfect when you want nuanced insights, real stories, or to discover issues you didn’t anticipate. For free trial users, especially, giving space to share thoughts is invaluable—about 43% of churn is linked to confusion about next steps during onboarding [1]. Here are ten open-ended questions that work exceptionally well for activation barrier surveys:

1. What were your first impressions when you started using our product?

2. Was there anything that confused you or slowed you down during setup?

3. What did you expect to accomplish in your first session, and what actually happened?

4. Are there any steps or features that felt unnecessary or complicated?

5. What’s the main reason you haven’t engaged more with the product since signing up?

6. What information or help would have made getting started easier?

7. Can you describe a moment when you felt stuck or frustrated?

8. Did you have any questions that went unanswered while onboarding?

9. How does our onboarding compare to others you’ve tried?

10. If you could change one thing about your activation experience, what would it be?

The best single-select multiple-choice questions for Free Trial Users survey about activation barriers

Single-select multiple-choice questions are a great fit when you need to quantify answers, track trends, or kick off a deeper conversation. Sometimes it’s easier for users to identify a barrier if you offer options—then you can dig deeper with targeted follow-ups. Given that 90% of users abandon a product if they don’t see value within the first week [1], structuring these initial questions sets you up for faster, actionable insight.

Question: What was the biggest challenge you faced when trying to get started?

• Understanding how to use core features

• Completing the sign-up or setup process

• Lack of instructions or guidance

• Finding relevant help or documentation

• Other

Question: How easy was it to find the main value or “quick win” in our product?

• Very easy

• Somewhat easy

• Neutral

• Somewhat difficult

• Very difficult

Question: What type of onboarding support do you prefer?

• Guided walkthrough (product tour)

• Video tutorials

• Step-by-step checklist

• Live chat with support

• Other

When to follow up with "why"? Any time a user picks an option that points to friction, confusion, or disappointment, it’s time for a well-phrased “why?”. For instance, if a user selects “Very difficult” in the value question, follow up: “Can you share more about what made it difficult to find value?” This simple nudge often reveals insights you’d miss otherwise.

When and why to add the "Other" choice? Always include “Other” when there’s a chance your pre-set options may not cover every situation. This lets users flag unfamiliar friction points—which, when investigated with follow-up questions, can uncover totally unexpected activation hurdles.

NPS question: Should you use it for Free Trial Users onboarding?

Net Promoter Score (NPS) is a simple, proven way to measure overall user sentiment. For free trial users, using an NPS question can spotlight early impressions and indicate who’s likely to promote—or quickly abandon—your product. Because 62% of new users form their opinion within the first three interactions [1], asking about likelihood to recommend right after onboarding is insight you don’t want to miss. Generate an NPS survey for free trial users in one click, or include the NPS question in your conversational survey to compare early sentiment with deeper contextual feedback.

The power of follow-up questions

Too many surveys stop at the first layer of feedback. But, like any great interviewer, we know that the right follow-up question unlocks context and meaning. With Specific, automated AI follow-up questions are generated in real-time—no script-writing, no manual probing, just deeper insights as if a live expert was running the interview.

• Free trial user: “I couldn’t figure out what to do after signing up.”

• AI follow-up: “What specifically was unclear or missing for you after signing up?”

Without this follow-up, you might never know that the real blocker was, for example, lack of an onboarding checklist—a feature that can make users three times more likely to convert [1].

How many followups to ask? Generally, 2-3 follow-up questions are enough to capture meaningful context without survey fatigue. With Specific, you can set this per question, and allow respondents to skip ahead if you’ve already got what you need.

This makes it a conversational survey: because you’re not just collecting answers—you’re having a dialogue. Respondents actually feel heard. It’s what conversational surveys are all about.

AI survey response analysis: Even when dozens of users write long, messy open-ends, it’s easy to analyze responses using AI. Summaries, theme extraction, segmentation—it’s all possible with zero spreadsheets, and your team can instantly chat with the results for fast answers.

In practice, these AI-powered followups are a game changer. If you’re curious, build a survey for free trial users now and see how effortlessly you can uncover what really matters.

How to compose effective prompts for AI survey generators

If you want AI to help you come up with questions, start simple and iterate. For example, you might ask:

Suggest 10 open-ended questions for Free Trial Users survey about activation barriers.

But context always improves results. Try:

We’re building a SaaS tool and want to understand what stops free trial users from activating and reaching “aha” moments. Suggest 10 open-ended questions to uncover the top barriers, confusion, and quick wins that shape user onboarding.

Once you’ve got a question set, ask the AI:

Look at the questions and categorize them. Output categories with the questions under them.

Then, pick the categories that matter most, and drill down:

Generate 10 questions for the “Onboarding Experience” and “Help and Support” categories.

What is a conversational survey? (And why AI-generated is different)

A conversational survey is built as a natural-flowing dialogue, not a rigid form. The AI adapts to each respondent’s answers, asks clarifying questions or skips when it detects comprehension, and delivers the entire survey in a chat interface that feels refreshingly simple. This is what lets you go beyond “check the box” feedback and capture what’s truly driving (or blocking) activation.

We built Specific to offer the smoothest, most natural user experience for conversational surveys—making it enjoyable for both creators and the free trial users who respond. If you want to go deeper, I recommend this guide on how to create a Free Trial Users survey about activation barriers. It’ll help you get started instantly, whether you’re using AI prompts or tweaking templates in the AI survey editor.

Why use AI for free trial user surveys? In a few minutes you can have a tailored, conversational, and adaptive survey—one that surfaces activation barriers, not just surface-level gripes. You don’t have to guess what to ask, or interpret vague responses alone. AI survey examples let you iterate swiftly, adapt based on user behavior, and unlock feedback that moves the needle for your product onboarding—without chasing users down or reading between the lines for insight.

See this Activation Barriers survey example now

Don’t miss out on powerful user insight. See how conversational AI surveys can surface blockers and quick wins—fast, engaging, and ready to deliver answers from your free trial users today.