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Voice of the customer analysis: best questions onboarding teams should ask for deeper customer insights

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Adam Sabla

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Sep 10, 2025

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Voice of the customer analysis during onboarding gives you a window into what new users really think, need, and struggle with. When you zero in on onboarding feedback, you start surfacing the raw details about your customer’s goals, points of friction, and the moments where something finally "clicks."

AI-powered conversational surveys are game-changers here. They ask questions like a thoughtful interviewer, not just a checkbox form, and unlock richer context with every response.

Core questions to understand customer goals during onboarding

Getting to the heart of your customer’s goals early shapes every step of their journey. When you ask the right questions up front, you start aligning your onboarding experience with what customers actually want—not just what you think they want. And that’s critical, especially as AI-powered sentiment analysis in voice of the customer (VoC) programs can boost Customer Satisfaction (CSAT) scores by up to 25% in just six months [3].

Here are foundational questions focused on user goals—with examples of what each uncovers and how Specific’s conversational AI can dig for more:

  • What do you hope to achieve by using our product?
    This question reveals each customer’s big-picture motivation.

    Can you tell me more about why this goal is important to you right now?

  • Which features are you most interested in exploring first?
    This exposes anticipated value and highlight priorities to optimize onboarding flows.

    What about that feature caught your attention? Is there a specific challenge you’re aiming to solve?

  • Is there anything you’re hoping this product will do that others haven’t?
    Counters assumptions and keys you into unmet needs or pain points from past experiences.

    What happened with other tools you tried? Was there a specific blocker?

  • How will you define success with our product in the first month?
    This clarifies what "winning" looks like for each user in their terms.

    Are there specific metrics, tasks, or feelings that tell you you’re on the right track?

AI follow-ups flip generic answers into actionable insights by persistently unpacking context—not just accepting “surface” responses. Because these probes are woven seamlessly into conversational surveys, the experience stays natural, relaxed, and never feels like an interrogation. That explains why users are consistently more engaged than with static forms—and why 75% of online shoppers now prefer AI-driven, conversational interactions [5].

Questions that uncover setup friction and barriers

Discovering exactly where users get stuck or lost makes the difference between smooth onboarding and silent drop-off. Strategic inquiries in your onboarding conversational survey quickly surface confusion, pain points, and obstacles—so you can address them before they drive users away.

  • Was there any point in the setup that felt unclear or confusing?
    This pinpoints specific UX/UI hang-ups and unclear documentation flows.

    Which part was confusing, and what do you think would have helped clarify it?

  • Did you run into any roadblocks while getting started?
    Goes direct to workflow-breaking moments—be it data import, integrations, or onboarding tours.

    What were you hoping to see or do at that step?

  • How confident do you feel using the product so far?
    Adds a quantitative lens to friction—low confidence hints at lingering questions.

    What would make you feel even more confident about using the product’s key features?

  • Were there any features or terms you didn’t understand?
    Identifies places where technical language or product naming trips users up.

    Is there a specific word or feature name you’d like us to explain differently?

The power of these questions is in timing—they land fresh, right after a user interacts with the relevant part of the setup. With in-product conversational survey widgets, you can trigger feedback requests after key events (like completing setup or activating a feature) for maximum relevance and actionable data.

Generic feedback

Friction-specific questions

“How was your onboarding experience?”

“Was there any step that felt unclear or confusing?”

“Anything to improve?”

“Did you run into any roadblocks while getting started?”

As VoC tools become more advanced—growing by nearly 19% CAGR and poised for massive adoption [2]—asking the right friction-aware questions upfront is becoming standard.

Capturing first value moments and early wins

The most successful onboarding experiences are those where customers quickly realize genuine value—the “aha!” that makes them stay. These moments aren’t random; they’re repeatable, and they predict long-term engagement and retention. By capturing them, you set yourself up to create more fans, faster.

  • When did you first feel like our product was helpful?
    This direct question surfaces the specific trigger for the user’s “aha!” moment.

    What was happening just before you discovered this value?

  • Was there a feature or experience that surprised you (in a good way)?
    Finds delight factors you can celebrate and double down on.

    Why was that unexpected, and how did it change your opinion of the product?

  • What did you accomplish with the product that you weren’t expecting so soon?
    Maps to over-delivery—what users achieve vs. what they assumed they could.

    Can you share a bit more about how you achieved that?

  • Was there anything that made you realize, “I’m glad I signed up”?
    Zeroes in on emotional and practical turning points in the onboarding flow.

    What about that moment stood out to you? Would you recommend it to others?

Replication opportunity: When you know what actually creates successful first impressions, you can design your onboarding flows and nudge other users toward those moments. Conversational surveys powered by Specific can adapt in real-time—probing deeper if a user hasn’t yet found value, or celebrating when they have—thanks to adaptive follow-up logic. By supplementing feedback with voice and text interaction analysis, organizations are staying ahead, as 60% are expected to do by 2025 [1].

Making voice of the customer analysis work in your onboarding flow

With onboarding, timing means everything. Immediate questions work best for the setup phase—asked right after the user completes a step, they catch impressions while they’re fresh. For early value and deeper outcome insights, a delay of a few days lets users explore and achieve something meaningful.

  • Trigger goal and expectation surveys on signup or after a user's first login.

  • Prompt feedback about setup friction right after a key event—like connecting an integration or reaching a product milestone.

  • Circle back for early value realization one week after onboarding completes.

Behavioral triggers ensure surveys are shown at exactly the right moment—and with tools like Specific’s AI survey generator, you can create custom onboarding surveys in just minutes, using a tailored prompt. For example:

Build an onboarding feedback survey for new SaaS users that asks about their initial goals, setup friction, and the first value they found.

Contextual timing ensures you always ask the right questions after the right event—think setup completion, first feature used, or first product milestone. To prevent fatigue, throttle surveys so new users aren’t overwhelmed; one or two bite-sized conversations are far more effective than a flood of questions. With the AI survey editor, you can adjust and refine questions easily based on the patterns you spot in early feedback.

Dynamic follow-ups keep every conversation feeling human and relevant, making the survey itself an engagement driver. Discover more about what makes automatic AI follow-up questions so powerful in voice of the customer analysis.

AI enhancements in VoC tools are already improving feedback accuracy by up to 69% [7], translating to sharper, more actionable insights for every onboarding team.

Transform onboarding insights into customer success

Getting onboarding feedback right with voice of the customer analysis isn’t just about collecting opinions—it’s about predicting long-term customer success. When you analyze response patterns across segments with AI-powered survey response analysis, you unlock trends that drive real results.

Create your own survey and start surfacing patterns that accelerate customer growth and retention—the process takes minutes and starts paying off immediately.

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Sources

  1. Gartner. 60% of organizations will augment traditional VoC with voice/text analysis by 2025.

  2. Grand View Research. Global VoC analytics segment size and forecast.

  3. CH Consulting Group. ROI of AI-powered VoC sentiment analysis.

  4. Widewail. 2024 statistics for negative communication mentions and wait time drops in customer feedback.

  5. Zipdo. Conversational AI acceptance in online customer service.

  6. Kings Research. E-commerce growth driving VoC investment.

  7. Global Growth Insights. Feedback accuracy improvement from AI predictive analytics in VoC.

Adam Sabla - Image Avatar

Adam Sabla

Adam Sabla is an entrepreneur with experience building startups that serve over 1M customers, including Disney, Netflix, and BBC, with a strong passion for automation.

Adam Sabla

Adam Sabla is an entrepreneur with experience building startups that serve over 1M customers, including Disney, Netflix, and BBC, with a strong passion for automation.

Adam Sabla

Adam Sabla is an entrepreneur with experience building startups that serve over 1M customers, including Disney, Netflix, and BBC, with a strong passion for automation.