User interview methods and the best questions for user interviews: how to get actionable insights with AI-powered surveys

If you’ve spent any time designing user interview methods, you know that the best questions for user interviews aren’t “one size fits all.” Each scenario—from discovery interviews to churn interviews and onboarding interviews—demands a unique approach. As AI-powered conversational surveys become the new standard, scaling rich, context-aware interviews is more achievable than ever. You can spin up tailored surveys or interviews in minutes using tools such as Specific’s AI survey builder.

Discovery interviews: uncovering what users really need

Discovery interviews focus on identifying unmet needs, pain points, and user motivations—crucial for shaping products with real impact. These interviews are goldmines for actionable insights if you ask well-crafted questions and follow up dynamically. Research shows that 85% of teams conducting in-depth discovery interviews say it significantly improves product development [2].

• “Walk me through how you currently solve this problem.”
  This surfaces context about existing workflows and highlights hidden pain points.

• “What’s the hardest part about [problem/goal]?”
  Pinpoints specific hurdles users face, whether systemic or situational.

• “Have you tried any tools or solutions—what worked, what didn’t?”
  Reveals user preferences and where your product could stand out.

• “Can you recall the last time this issue impacted you?”
  Draws out recent, relevant examples for tangible insights.

• “If you could wave a magic wand, what would your ideal solution do?”
  Opens the door for creative, unconstrained feedback that can inspire breakthrough ideas.

• “How do you feel when you encounter this problem?”
  Gets to the emotional drivers behind user frustrations.

• “Is there anything about this process that surprised you?”
  Unearths overlooked or counterintuitive friction points.

AI follow-up strategy: Advanced AI can dig deeper into any interview response, surfacing context that scripted questions miss. For instance, when a user mentions a vague pain point, AI follow-ups clarify specifics or gently probe for underlying causes. Here’s an example follow-up configuration:

For every mention of a challenge or frustration, ask the user to share a recent example. Then clarify what made it particularly difficult, and probe to uncover any workarounds or hacks they've tried.

With Specific’s automatic AI follow-up questions, you create a natural, branching dialogue that helps you reach the heart of every user need—without adding friction to the interview process.

And if you want to go even deeper with your insights, you can use AI to analyze responses and uncover hidden themes. This often leads to richer, more specific answers than traditional survey forms [1].

Churn interviews: understanding why users leave

Churn interviews are all about empathy and timing—your goal is to identify the true “why” behind user departures, so you can address root causes and boost retention. Striking the right tone is critical, as is asking follow-up questions that don’t feel like cross-examination. Contextual inquiries show that with just 5–10 interviews, you can surface 70% of the most valuable feedback on churn [3].

• “Can you share what led to your decision to leave (or consider leaving)?”
  Opens the conversation with empathy and gives the user control over the narrative.

• “Was there a specific experience or frustration that tipped the balance?”
  Pinpoints events or pain points that accelerated churn.

• “Did anything about the product/service not meet your expectations?”
  Highlights gaps that can become quick wins for retention.

• “Were there features or aspects you wish were different?”
  Invites users to envision improvements, reducing defensiveness.

• “Did you consider alternatives—and if so, what stood out about them?”
  Provides competitive context.

• “How did you originally hope the [product/service] would help you?”
  Uncovers misalignments between value proposition and actual usage.

• “Would you reconsider staying if something changed? If yes, what?”
  Reveals opportunities to win back users or improve future retention.

Churn-specific AI probing: In churn interviews, you want AI to delicately probe for the real motivation behind leaving—without causing defensiveness. Use a configuration like this:

After the user shares their reason for leaving, gently ask for a specific moment or example that made them feel this way. Make sure your tone is caring, avoid sounding blameful or demanding, and thank them for their honesty.

This conversational AI approach keeps things human—and reduces the survey abandonment that’s so common when addressing sensitive topics.

Onboarding interviews: capturing first impressions

Feedback from onboarding interviews shapes your understanding of first-time experiences—key for driving adoption, reducing friction, and building loyalty. The right prompts spotlight moments of delight and confusion, giving you a continuous improvement loop.

• “How easy was it to get started with [product/service]?”
  Surfaces blockers and usability friction right out of the gate.

• “Was there anything about the process that was confusing or unclear?”
  Pinpoints documentation gaps or UI/UX improvements.

• “What was the very first thing you wanted to accomplish?”
  Reveals intent and desired outcomes that the onboarding flow should enable.

• “How did you feel after completing the onboarding?”
  Measures confidence and satisfaction, not just completion rates.

• “Is there anything you wish you’d known before starting?”
  Invites suggestions for content or orientation enhancements.

• “How would you describe the onboarding experience to a friend?”
  Uncovers emotional and social context around first impressions.

• “What could have made your first day better?”
  Opens the door for candid feedback about personal needs or expectations.

Onboarding follow-up configuration: AI follow-ups during onboarding interviews should clarify any vagueness and probe for emotional highs or lows. Configure like so:

If the user mentions anything confusing, ask specifically which step or screen was unclear, and what would have helped them move forward confidently. For positive feedback, ask what stood out most and why.

Delivering onboarding interviews through in-product conversational surveys lets you capture this feedback at just the right moment. It’s especially powerful when paired with multilingual support—meeting users in their preferred language to boost both participation and quality.

Configuring AI follow-ups for deeper insights

Configuring your AI follow-up prompts is about combining empathy, clarity, and context. Here’s what great configurations look like—each one custom-tailored for a different interview type.

Discovery interview, deep dive:

“After each pain point is mentioned, politely ask for a concrete recent story or scenario, and clarify what would have prevented the pain.”

Churn interview, gentle probing:

“If the user shares a negative experience, thank them, and invite them to expand on when it happened, what they tried to fix it, and how it made them feel.”

Onboarding interview, clarity focus:

“When a user describes something as ‘confusing,’ immediately follow up to highlight which part and what instructions or resources could have made it easier.”

General open-ended survey:

“For every broad or vague answer, politely prompt the user to give a concrete example or suggestion.”

Adjust how many follow-ups the AI should attempt (usually one or two per question strikes a good balance) and set a friendly, neutral tone. With the AI survey editor, making these adjustments is straightforward—just describe the changes in natural language, and it’s done.

AI-powered follow-up questions transform interviews from static exchanges to meaningful conversations—yielding depth and detail that forms fill-in surveys rarely achieve [1][6].

Start conducting better user interviews today

Combining the right user interview questions with smart AI-powered follow-ups unlocks richer, actionable insights. Create your own survey with conversational AI, and experience how intuitive, responsive interviews quickly surface the truth behind user decisions.