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Open-ended feedback: best questions AI follow-ups to unlock deeper insights

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Adam Sabla

·

Sep 12, 2025

Create your survey

Getting valuable open-ended feedback isn't just about asking questions—it's about asking the right questions that spark meaningful conversations.

With AI follow-ups, the best questions are those designed to trigger deeper exploration, inviting your respondents to open up beyond surface answers.

Let's explore proven question formats that work exceptionally well with Specific's AI, so you can extract the richest insights possible.

What makes a question perfect for AI follow-ups

Not every open-ended question is created equal: the best ones are broad enough to leave space for elaboration, but focused enough to draw out relevance to your topic. When I craft questions, I look for that sweet spot—just enough ambiguity so AI follow-ups have something to clarify, dig into, or contextualize. This design invites richer stories and more meaningful insight.

For example, industry research shows that framing questions to involve respondents in the problem can elicit much more thoughtful feedback than generic queries. Asking, “This brand is more popular among some people than others, and we are trying to understand why,” goes further than “Why do you like this brand?” [1] The point is to draw respondents in, giving the AI more to probe.

Starting broad: I recommend opening with questions like, “Tell me about your experience”—these give respondents space to share what matters most to them, and allow AI to navigate deeper by probing for details or asking for clarifications as the conversation unfolds.

Emotional triggers: Questions that tap into feelings—such as “How did using this product make you feel?”—often generate responses full of nuance and context, giving the AI plenty of threads to explore.

Context invitations: Whenever you ask for examples or stories, such as “Can you share a situation where our service really helped (or let you down)?”, you’re giving the AI natural opportunities for follow-up, like, “Could you walk me through what happened next?” These formats consistently deliver the richest, most actionable feedback because of the context they generate.

Best questions for different feedback scenarios

Let me share some of the most effective open-ended feedback questions, with variations tailored for rich AI follow-up in Specific:

  • Product feedback: “What’s been your experience using [product] so far?”
    This invites stories, not just facts, and lets the AI probe specific features or pain points respondents surface.

  • Customer satisfaction: “How would you describe your recent interaction with us?”
    You get a broad narrative, and the AI can dig into the highs or lows they mention by asking, for instance, “What made it stand out?”

  • Feature requests: “What would make [product] more valuable for you?”
    This is a gold mine for AI-driven exploration of concrete use cases or unmet needs.

  • Problem discovery: “What challenges are you facing with [specific area]?”
    This helps identify root causes, and the AI can naturally ask, “How do these challenges affect your workflow?”

  • Experience mapping: “Walk me through how you typically use [product].”
    Great for storytelling, enabling the AI to follow up on steps, obstacles, or delightful moments.

These questions perform so well because they invite stories, texture, and concrete examples—everything AI needs to launch meaningful follow-up prompts. Want to see how this works for live surveys? Check out some of our favorite conversational survey examples for inspiration.

As a bonus, challenging respondents or bringing them into the problem (like, “This product works better for some people than others. What’s been your experience?”) generally leads to more insightful answers—and gives the AI more avenues to explore [1].

Controlling tone for better AI conversations

When you use Specific, you can define the tone your AI takes with respondents—this isn’t just a cosmetic setting; it shapes the quality and depth of the feedback you collect.

Professional tone: This is perfect for B2B or high-stakes feedback, prompting respondents to give thoughtful, detailed answers while the AI follows up in a manner that feels respectful and considered.

Casual tone: When you want honest, unfiltered thoughts—say, in consumer research or community feedback—a more relaxed tone helps people open up and speak like they would to a friend.

Brief tone: If you just need high-level insights (or know your audience is pressed for time), keep it concise. The AI will ask for specifics but won’t overwhelm respondents with too many or too deep follow-ups.

Tone doesn’t just affect the AI’s language, but also the kinds of responses you get. Plus, you have full control over what the AI should dig into or leave alone—whether you want it to probe motivations, avoid pricing, or skip personal info entirely. That’s all easily adjustable in the AI survey editor.

Prompt example: "Use a friendly and approachable tone. After each answer, ask for a real-life story or example, but avoid asking about pricing."

Making your questions work across languages

One of my favorite things about Specific is its support for multilingual feedback. The platform automatically handles translation, displaying surveys based on each respondent’s app language. But clever question design still matters for seamless, high-quality AI follow-ups in every language.

Avoid idioms: Keep language straightforward to prevent cultural references from confusing translations or AI logic. “Share a story where this product was especially helpful” is universal; “It knocked it out of the park” is not.

Use simple structures: Clear, direct, present-tense sentences translate reliably and help AI generate natural follow-ups in any language.

Test with native speakers: Even with AI-powered translation, I run final drafts past native speakers to make sure the conversation feels natural everywhere.

When multilingual mode is on, respondents get the full survey experience in their chosen language—AI and all. The AI adapts, keeps the conversation flowing, and delivers probing questions without losing context.

Good practice

Bad practice

"Describe a time when our product helped you."

“When did it knock your socks off?”

"What features would you add if you could?"

“What bells and whistles are missing?”

In summary: keep it clear, direct, and universally understandable. That’s how you make sure your conversational survey with AI follow-ups delivers consistent quality, no matter the language.

Advanced strategies for richer AI conversations

Once you’ve mastered the basics, take open-ended feedback to the next level using a few advanced tricks:

Layer your questions: Start with something broad, then let AI probe for specifics, stories, or motivations. This approach mirrors the best qualitative research practices, where one prompt naturally leads to deeper insights (“Tell me about a challenge you faced. What happened next?”) [2]

Set follow-up boundaries: Define what types of info the AI should explore—and what to avoid. For instance, instruct the system not to probe into pricing or personal identifiers if those are irrelevant or sensitive to your context.

Use conditional logic: For scenarios like NPS, set the AI to follow up differently with promoters than with detractors. This ensures you don’t miss key detail—promoters get “What delighted you most?” while detractors get “What frustrated you?” It’s a two-track system for richer conversations.

  • You control follow-up intensity—from a single nudge (“Can you give me an example?”) to a multi-layered exploration (“Why, how, what next?”), depending on survey goals and audience patience.

  • Set a maximum follow-up depth to avoid respondent fatigue while still getting robust data.

  • Specific’s AI “remembers” earlier context, so every follow-up builds on previous answers, making the conversation feel natural and coherent.

Prompt example: "For NPS responses, if the score is 9 or 10, ask what delighted them most. If score ≤ 6, ask what frustrated them. Always avoid asking about competitors."

Transform your feedback collection today

The right open-ended questions, combined with AI-powered follow-ups, will transform the quality of your feedback from generic to insight-rich. With Specific’s AI survey generator, launching conversational surveys that probe for deeper insights is effortless—no scripting or manual analysis needed.

You get natural conversations, automatic analysis, and multilingual support without extra work. Create your own survey—it really is the fastest way to master the art of collecting feedback that matters.

See how to create a survey with the best questions

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Sources

  1. Kantar. Your guide for writing open-ended questions for more thoughtful feedback

  2. SurveyLegend. How to get people to answer open-ended survey questions

  3. Simplesat. What are open-ended questions in customer surveys? Definition, examples, and best practices

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.