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Voice of customer research: great questions for onboarding friction that reveal and resolve user pain points

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Adam Sabla

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Sep 8, 2025

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Voice of customer research during onboarding reveals exactly where new users get stuck and why they abandon your product. By zeroing in on onboarding friction, we can focus feedback collection to uncover—and fix—the spots causing drop-offs.

Understanding customer feedback as users move through onboarding isn’t optional—it’s the key to reducing frustration, boosting retention, and ensuring your product delivers from day one. Asking the right questions, at the right moments, exposes the real friction points most companies don’t even know exist.

When to ask for feedback during customer onboarding

Great feedback starts with getting the timing right. I’ve seen teams lose incredible insight by asking new users too late (when memories fade) or too soon (before any value is delivered). The most actionable feedback happens in context—right after a user completes a key action, encounters a blocker, or finishes a critical setup step.

Typical friction moments include:

  • First login or signup

  • Connecting data, teams, or integrations

  • Setting personal or business preferences

  • Navigating first-use checklists or dashboards

  • Encountering guided tours or tooltips

Triggering in-product conversational surveys at these moments means you capture feedback at the height of relevance, when pain points are freshest and specifics are top of mind. Here’s how timing plays out:

Good timing

Bad timing

Immediately after profile setup

Days after first login

Right after user hits a blocker (error/uncertainty)

After several support tickets have been filed

Once onboarding tasks or checklist at 80% completion

After onboarding is fully completed (memories fade)

When a user closes the onboarding tutorial

Randomly, with no context

Fresh perspective: Asking for feedback right after a setup step taps into that first emotional reaction—the delight, confusion, or frustration—before details blur.[1]

Context matters: Feedback that’s tied directly to user actions is more reliable and actionable. Contextual surveys within onboarding flows naturally deliver more honest and specific insights.[1]

Great questions to uncover onboarding friction

I rely on certain types of questions to spot friction, and mixing open-ended with structured options surfaces both depth and clarity. Here are my favorite picks:

  • What, if anything, confused you during this setup step?

    This open-ended question directly addresses immediate blockers. It’s great at surfacing that one tiny detail or instruction users miss, which might be invisible to an internal team.

    “Can you describe anything that was unclear or confusing during your initial setup?”

  • How easy or difficult was this part of onboarding? (Scale: Very Easy → Very Difficult)

    This structured question quantifies user effort, helping to spot steps that consistently underperform—data that’s invaluable for prioritizing improvements.

    “On a scale of 1-5, how would you rate the difficulty of connecting your account?”

  • Was there any information or guidance you expected but didn’t find?

    This quickly pinpoints missing help content, tooltips, or walkthroughs. When several users flag the same missing context, it’s a clear opportunity for quick wins.

    “What additional instructions would have helped you complete this step?”

  • What did you expect to happen next, and what actually happened?

    This one uncovers misaligned expectations—the source of many subtle drop-offs that crash activation rates.

    “Did anything about this process work differently than you expected? Tell us more.”

  • Was there a specific reason you almost stopped or considered quitting?

    You’ll be amazed how often small, solvable issues come up here—sometimes a confusing term, weird form, or hidden button.

    “At any point, did you feel like giving up? If so, why?”

Setup confusion: Direct questions about what was unclear help catch overlooked instructions, jargon, or steps that didn’t flow logically.

Missing guidance: Explicitly asking about missing help or content reveals where a guide, tooltip, or walkthrough would move users past a hurdle effortlessly.

Expectation gaps: When reality doesn’t match user expectations, it causes friction. Questions about what users thought would happen (versus what did) root out these silent killers.

How conversational AI surveys reveal hidden friction points

Traditional surveys stop where the form ends, but conversational AI-powered surveys take feedback to another level. When a user shares a vague or partial response—like “It was kind of tricky to set up”—the AI can immediately ask a clarifying follow-up to dig deeper, just like a human researcher would.

With automatic AI follow-up questions, you don’t need to guess what extra detail might matter. Let me show a few real examples of how AI drilling makes feedback gold:

  • If someone says, “The connection was confusing,” the AI can reply, “What about that step was most confusing for you?”

  • After a user notes, “I didn’t know which option to choose,” the AI follows up: “Which options were unclear or needed more explanation?”

  • If feedback is just “Okay”, AI can probe: “What would have made your experience great instead of just okay?”

Those follow-ups make a survey feel like an actual conversation—not just a questionnaire—drawing out details users wouldn’t type on their own. This is the essence of a conversational survey.

The beauty is in the AI’s natural ability to ask “why?” or “can you tell me more?” without feeling robotic or generic. That means deeper, story-driven feedback—and richer voice of customer data for your team.

Turning customer feedback into onboarding improvements

Once feedback flows in, the magic happens during analysis. Instead of sifting through spreadsheets, I let AI find the themes: is confusion highest during setup, integrations, or first-use settings? The AI survey response analysis lets you chat with AI about results, instantly surfacing what’s holding users back.

Want to find friction bottlenecks in your onboarding? Try one of these analysis prompts:

“Which onboarding steps do most users describe as difficult or confusing?”

“What’s the #1 theme among users who didn’t finish onboarding?”

“Summarize the most requested improvement ideas from onboarding feedback.”

Quick wins: When you spot clear patterns—multiple users stuck at the same field or dropping at the checklist—you can implement targeted fixes and measure the impact instantly.

Long-term fixes: Themes like repeated requests for video tutorials, better tooltips, or more personalized guidance reveal where a systemic update will improve the onboarding journey for everyone.

Best of all, you can simply chat with the AI about drop-off points, ask it to cluster pain points by user type, or explore correlations between feedback themes and ultimate user success.

Why voice of customer research transforms onboarding success

Better onboarding means better business. The data speaks for itself: companies with defined onboarding processes see a 50% increase in customer retention[1], and successful onboarding improves activation rate, leads to a faster time to value, and reduces the volume of support tickets.

Think of the ROI from multiple angles:

  • Less support burden: less confusion means fewer tickets and manual intervention

  • Higher activation: more users complete setup, experience value, and stick around

  • Lower churn: well-onboarded customers are proven to stick with products longer[1]

If you’re worried onboarding surveys might delay or annoy users, remember: people want to give feedback when it feels personal and conversational. In fact, a chat-based survey can increase engagement—even making feedback feel like a part of the product, not an interruption. Users expect seamless, fast, easy onboarding (75% according to recent stats)[1], so missing this feedback is a massive lost opportunity.

It all comes back to customer-centricity. When you listen at every step, act on what you hear, and improve friction points in onboarding, everything else—loyalty, word-of-mouth, revenue—follows.

Start collecting onboarding feedback today

Voice of customer research unlocks a smoother onboarding, higher retention, and fewer abandoned signups. Specific provides the most intuitive, AI-powered survey creation, blending best-in-class chat experience for users and effortless setup for teams. Ready to discover real friction points? Create your own survey now—don’t leave insights on the table.

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Sources

  1. Wifitalents.com. Customer onboarding statistics: The numbers you need to know for retention and growth

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.