Running a well-crafted survey interview during onboarding can be the difference between users who stick around and those who disappear after day one.
This article shares proven questions and strategies for uncovering what new users really think during their first week, so you can improve your onboarding experience where it counts most.
Essential questions for day 1-3 onboarding interviews
Getting first impressions right is everything. In fact, 75% of users abandon a product within the first week if they struggle during onboarding—so it pays to know exactly where new users get stuck or wowed. [1]
What made you decide to try [product] today?
This opener reveals a user’s true motive—did they see an ad, hear from a friend, or hit a pain point? It helps you target messaging and highlight what drives adoption.What’s the main problem you’re hoping we’ll solve for you?
Understanding this paints a clear picture of user intent, ensuring your product features and onboarding communications emphasize core value.How did you feel about our sign-up process?
Was it smooth or did anything cause friction? Answers here can uncover UX issues or accessibility problems, both of which are major churn factors.Was anything confusing or unclear when you first logged in?
Pinpoints where your instructions, labels, or page hierarchy might fall short. Don’t assume users read docs—they live in the moment.How does this compare to what you expected based on our website/marketing?
Users often arrive with assumptions. Finding misalignments lets you fix overselling or clarify ambiguous web copy.Did you notice any features you weren’t expecting, or miss anything you hoped to find?
This surfaces both delightful surprises and critical “missing” features, allowing you to iterate the onboarding flow or product roadmap.How likely are you to keep using the product after today? Why?
Not just a vanity question—the reasons users give shed light on motivating or discouraging early experiences.
When a response feels vague (“Not sure what I expected”), let AI follow-up questions step in. With Specific, the survey can automatically probe deeper—think of it as an expert interviewer asking “Can you give an example?” or “Why was that unclear?” right when it matters. This leads to richer, context-driven insights no form can match.
Scenario-based prompts to uncover first-week friction
Sometimes the best way to diagnose an onboarding problem is to have users walk you through specific moments. Scenario-based questions force recall—bringing to light tangible experiences and in-the-moment feelings, instead of wishy-washy summaries.
Can you describe the first time you tried to set up your account?
This prompt helps spot technical hurdles or misunderstood requirements during setup.Tell me about a point in your first week where you felt stuck or unsure what to do next.
This reveals gaps in guidance or onboarding nurture emails that leave users guessing.Was there a feature you tried to use, but couldn’t figure out how?
It’s a goldmine for identifying poorly surfaced or inadequately explained functionality.Can you remember a moment something worked better than you expected?
Friction isn’t all bad—collecting these stories can validate what you’re doing right, which you can amplify for future users.What was the very first “aha” moment you experienced after signing up?
Pinpoint these sparks—help all new users get there, faster.
Specific’s AI doesn’t just collect answers—it analyzes them. When users describe specific friction, those messy handwritten notes are instantly grouped, summarized, and segmented by onboarding step, thanks to the AI-powered analysis. Here’s how you might prompt the AI to make sense of a scenario-based survey:
Group all described friction points by the onboarding step during which they occurred (signup, profile setup, feature discovery, etc). Provide a summary of the main issues for each step.
Identify and list common patterns in user confusion during their first week, with direct quotes from respondents for each pattern.
Highlight delight moments and describe the product triggers that led to them. Suggest ways to help more users reach these moments in week one.
Conversational surveys like those from Specific absolutely excel at scenario-based prompts. The AI naturally asks clarifying questions—if a user mentions a confusing popup, it responds: “What about the popup was unclear?” or “How did you try to resolve the confusion?” The conversation brings context you can actually act on.
Timing and targeting your onboarding survey interviews
When you ask matters as much as what you ask. Catching users at just the right moment—right after completing setup, on day three of the trial, or immediately following their first “aha” moment—yields the clearest feedback. Behavioral triggers help you tie survey delivery to key milestones.
Using in-product conversational survey widgets, you can target different user segments. New users might need more guidance, while returning users give you feedback on changes or compare experiences. Advanced targeting ensures each survey feels highly relevant.
Traditional feedback forms | Conversational onboarding interviews |
|---|---|
Bland, one-size-fits-all questions | Dynamic, personalized, and contextual follow-ups |
User often abandons forms midway | Chat-like conversations hold engagement longer |
Little clarification—vague responses go unexplored | AI probes for clarity, unpacks real needs |
Results siloed, analysis is manual | Automatic grouping and insight by step or cohort |
Tends to disrupt onboarding flow | Non-intrusive widget adapts to user behavior |
Widget placement matters. By placing in-product surveys at logical moments (e.g., page overlay post-setup or subtle chat launch in the corner), you let users provide feedback without yanking them from their flow. This respect increases both completion rates and the candor of responses.
Frequency controls are key. With Specific, you can set surveys to appear once per milestone or per cohort, ensuring you avoid survey fatigue but still gather insights at critical junctures. Combined with robust targeting, you’ll reach the right users with the right question—never asking the same person twice unless you mean to.
From insights to action: improving your onboarding flow
Once you’ve collected onboarding interviews, the real work begins—turning messy raw feedback into strategic improvements. The best approach? Group and analyze responses by onboarding step or user segment, then use AI to uncover patterns that might otherwise stay hidden. For example, you might find that 63% of customers consider onboarding when deciding to purchase—that’s not just theory, that’s how users really behave. [1]
Specific makes this easy. With AI-driven survey response analysis, you can:
Auto-group feedback by journey step (“signup confusion”, “first feature activation”, “first time stuck”)
Spot and quantify themes (recurring roadblocks or delight triggers)
Slice responses by user cohort—see what’s different for new signups versus power users
Chat with the AI directly: e.g.,
Based on this week's interviews, what are the most common drop-off points and how have they changed versus last month?
To prioritize, focus on friction points that block many users or those that occur early in the journey—since 70% of customer churn happens in the first 90 days. [2] Little wins, like clarifying a tooltip or adding an onboarding checklist, can decrease week one drop-offs dramatically.
Improvement isn’t a one-off job. The most successful teams run regular onboarding interviews to keep up with fresh usage patterns and iterate their flows. With the AI survey editor, you can easily refine your interview questions as you learn—just describe what you want in natural language and let AI update your survey. Here’s an example iteration:
Add a follow-up to the first login question: “What would have made your start easier?” Then group these suggestions by product team area (UI, support, docs, etc).
Don’t underestimate what you’re missing: If you’re not interviewing new users during onboarding, you’re missing critical insights about why they succeed or fail—and risking higher churn for preventable reasons.
Start collecting onboarding insights today
Great onboarding starts with understanding your users’ actual experience, not just what you hope they see.
It only takes a few minutes to create your own onboarding survey and start gathering insights that fuel smarter onboarding improvements.