Remote user interview: best questions customer discovery teams should ask for deeper insights

If you want real answers from a remote user interview, it pays to ask the right questions. Remote customer discovery is at the heart of finding out what users want, what frustrates them, and what they’re already using. Great questions are how you uncover Jobs to Be Done (JTBD), dig up pain points, and discover the alternatives people rely on when your solution doesn’t fit.

This guide shares the best questions for remote customer discovery—plus AI-powered strategies that go deeper, so your next survey is smarter and more insightful.

Questions to uncover Jobs to Be Done

At its core, Jobs to Be Done (JTBD) is about what users “hire” your product to do. By zooming in on goals, not just features, you’ll spot real opportunities for breakthrough value. Here’s how to dig beneath the surface:

• “What were you trying to accomplish the last time you used a similar tool?”
  Unpacks the real-life context and intent.
  AI follow-up: Ask about the specific situation, urgency, and who else was involved.

• “Can you walk me through how you solved this problem before discovering our product?”
  Highlights the process and where friction happened.
  AI follow-up: Probe for detailed steps, emotions at each stage, and what “worked” or fell short.

• “When you needed to get this done, what didn’t work with your previous approach?”
  Zeros in on unmet needs.
  AI follow-up: Explore what would have made their experience easier or better.

• “If you could wave a magic wand, what would make getting this job done effortless?”
  Invites users to dream, revealing aspirations and hidden blockers.
  AI follow-up: Encourage specifics—not just “easier,” but how and why.

You can generate tailored JTBD surveys instantly using the AI survey generator—just describe your product or challenge and let the AI suggest smart, open-ended questions.

Tip: Use JTBD questions early in the interview to set context, but then drill down with concrete stories.

Analyze this user response for core JTBD insights:

"Last week I needed to share files with my team quickly. I used email, but some attachments bounced back. I ended up using Dropbox, but it was slow to get everyone on board."

Research shows that asking open-ended “what are you trying to get done?” questions not only draws out user goals but also reveals workflows and motivations traditional forms miss. [5] That’s why AI-powered conversational surveys consistently deliver richer data. [1]

Questions to identify user pains and frustrations

Understanding user pains is where the big wins hide. People remember pain—those jobs that are annoying, slow, or error-prone. When you know what users hate, you know what to fix (or avoid copying from others).

• “What’s your biggest frustration with your current process?”
  Gets users to open up quickly.
  AI follow-up: Have the AI ask “how does that impact your day?” or “what emotions come up when that happens?” to reach the root.

• “Tell me about a recent time when something didn’t work and how you handled it.”
  Focuses on real events, not hypotheticals.
  AI follow-up: Probe for the chain reaction—missed deadlines, extra steps, or lost opportunities.

• “Are there any steps that feel especially slow or time-consuming?”
  Flags ripe places for improvement.
  AI follow-up: Ask if they’ve found workarounds or just tolerate it.

• “What do you wish could be automated or done for you?”
  Uncovers hidden pain and desire for simplicity.
  AI follow-up: Encourage specifics and real examples.

This is where tools like automatic AI follow-up questions shine—they probe for emotional depth, making it easier to spot not just what’s annoying, but what’s truly painful for users.

Example: If a response is vague (“It’s sometimes slow”), AI can follow up with: “Can you remember the last time it slowed you down? What happened as a result?” That prompts specifics you can actually use.

Studies confirm that conversational, probing interviews consistently reveal insights missed by static forms, and that innovative tools (even using video or smart glasses for usability) can boost both depth and breadth of pain signals in remote research. [2][3]

Questions about alternatives and current solutions

Knowing which alternatives users use (or have tried) reveals your competition and what drives someone to switch. It’s not just about features—switching triggers, switching costs, and the subtle reasons people “just stick” or decide to try something new matter most.

• “What tools or solutions have you tried for this job?”
  Maps the competitive landscape.
  AI follow-up: Ask what worked or didn’t, how long each was used, and any surprises.

• “What would make you consider switching from your current tool?”
  Targets triggers and dealbreakers.
  AI follow-up: Probe for specific barriers (data migration, trust, cost) and what might overcome them.

• “Have you built any custom workarounds to make existing tools work better?”
  Signals the gaps no competitor has bridged.
  AI follow-up: Explore why these workarounds were necessary and if they’re sustainable.

• “Are there things you wish your current solution could do, but it can’t?”
  Uncovers gaps and future needs.
  AI follow-up: Ask about attempts to solve these with other products or hacks.

When analyzing alternatives, feed responses into AI survey response analysis for competitive insights. All you need is a simple prompt:

Summarize what competitor products users mention most, the top reasons for switching, and barriers that stop them from trying something new.

Conversational surveys—especially when deployed with AI agents—make users more comfortable sharing candid opinions about competitors than they’d admit on a call or in writing. They feel less “on record” and more open to tell you the good, the bad, and the unvarnished truth. Research confirms that well-structured, open-ended interviews (not just checkboxes) uncover these insights and shape more effective product strategy. [6][7]

Example remote discovery interview flow

Here’s a practical workflow I recommend (and use) for remote discovery:

1. Build your conversational survey: Combine JTBD, pain, and alternative questions in one flow. Set the tone to casual, curious, and non-judgmental—for richer stories. (Let the AI survey builder do the heavy lifting.)

2. Customize follow-up instructions: Direct the AI to dig deeper after any vague or general response—especially about pains, switching barriers, or workflow details.

3. Share via a landing page: Distribute easily using a Conversational Survey Page. Just send users the link—no setup or scheduling needed.

4. AI-powered follow-up flow: Real responses drive the next question. For example:
   User: “I spend a lot of time copying data between spreadsheets.”
   AI agent: “How often does that happen? What kind of data, and what’s the biggest challenge with the process?”
   User: “Weekly, and it’s sales figures. The biggest headache is that formulas break.”
   

   AI agent: “How do broken formulas impact your work or results?”

5. Refine and iterate: Use the AI survey editor to update and polish questions based on real-world early responses. Remove what’s confusing, double down on what drives stories.

For inspiration on the power of in-product and page-based conversational surveys, check our Conversational Survey Pages and compare with integrated Conversational In-Product Surveys. Both deliver natural insights, but page-based surveys are perfect for remote, async customer discovery interviews.

Research shows that AI-powered chat surveys with open-ended questions not only boost response quality, but make it practical to scale deep user research across hundreds of participants—way beyond what a single researcher could handle. [1][3]

Start your customer discovery today

The best insight comes from a mix of powerful questions and smart AI follow-ups. With conversational surveys, you can run scalable remote user interviews that don’t just gather feedback—they reveal what really matters. Ready to unlock higher-quality discovery? It’s never been easier to create your own survey and turn answers into action.