Design Thinking Questions: 30 Examples to Ask at Every Stage

Design thinking questions are open-ended prompts that help teams understand users, frame the right problem, and test ideas before they build. Good ones surface needs people rarely state outright. They move a team from “What should we build?” to “What does this person actually struggle with?”

Every innovation starts with a question, but not every question earns a useful answer. Yes/no prompts, leading wording, and solution-first framing quietly steer users toward what the team already believes.

In this blog, we’ll break down 30 design thinking questions organized by stage, with sample answers, techniques for digging deeper, and the mistakes that weaken user research.

What are design thinking questions?

Design thinking questions are open, neutral questions that teams use to explore a problem from the user’s point of view before committing to a solution. They show up in empathy interviews, workshops, prototype tests, and follow-up surveys.

Design thinking itself is a human-centered approach to problem-solving. The widely used five-stage model, popularized by the Stanford d.school, moves through empathize, define, ideate, prototype, and test. The stages loop rather than run in a straight line, so the questions loop too.

A design thinking question works when it produces a story, a reason, or a surprise. If it produces only a “yes,” a rating, or a polite compliment, it belongs in a different tool.

What makes a good design thinking question?

Strong questions share a handful of qualities. Use this list as a quick review before any interview or workshop.

• Empathetic: It shows real interest in the person’s experience, not in validating your idea.
• Open: It invites a story or explanation instead of a one-word reply.
• Neutral: It doesn’t hint at the “right” answer or praise your concept in advance.
• Problem-focused: It keeps attention on the core challenge rather than on features.
• Clear: It uses plain words, one idea at a time, with no jargon.
• Grounded in behavior: It asks what people did, not what they might do someday.
• Inclusive: It works for different user groups and invites perspectives beyond your core team.
• Iterative: It gets revised as you learn, rather than locked into a fixed script.

How are design thinking questions different from survey and interview questions?

Design thinking questions overlap with other research questions, but their goal is discovery, not measurement. The table below separates the terms people often confuse.

In practice, teams use all of them. Interviews and design thinking questions find the problem. Surveys tell you how widespread it is. Usability tests confirm whether your fix works.

Design thinking questions for each stage of the process

The fastest way to use the 30 questions below is to match them to where your project sits right now. Each stage of the design thinking process calls for a different kind of question, and mixing them up is a common reason research stalls.

Replace the brackets with your own task, product, or audience. Treat each list as a starting point, then follow the answers wherever they lead.

Empathize: 5 Empathy interview questions to understand users

Empathy questions help you see the problem through the user’s eyes. Ask about specific, recent moments, because memories of real events are more reliable than opinions.

Notice that each useful answer contains a detail you could act on. Capture those details on an empathy map, so the whole team sees what users say, think, do, and feel.

Define: 5 Problem definition questions to frame the right challenge

Problem definition questions turn raw interview notes into a focused challenge. They stop the team from solving a symptom, or the wrong problem entirely.

6. What problem are we solving, in the user’s own words?
   Example answer: “New hires can’t tell who to ask for help during their first week.”
7. Who experiences this problem most, and when?
   Example answer: “Remote hires in their first 10 days, mostly before their manager’s first one-on-one.”
8. What is the root cause, not just the symptom?
   Example answer: “Slow page loads come from uncompressed product images, not the server.”
9. What constraints must we work within?
   Example answer: “We have one quarter, two developers, and HIPAA rules on patient data.”
10. How will we know the problem is solved?
    Example answer: “Fewer than 10% of users abandon the form, down from about a third today.”

The answers feed directly into a problem statement, which becomes the brief for ideation.

Ideate: 5 How might we questions and prompts to generate ideas

Ideation questions widen the range of possible solutions before the team narrows down. Their job is quantity and variety first, quality later.

The most common format is the “How might we” question, which turns a problem into an invitation. The others below push teams past their first obvious idea.

• 11. How might we [reach an outcome] for [user] when [situation]? For example, “How might we help first-time parents feel confident about feeding schedules during the first month?”
• 12. What would we do with one-tenth of the budget? Tight limits force simpler ideas that often turn out stronger.
• 13. How would a completely different industry solve this? A hospital might borrow from airline check-in, or a bank from a ride-share app.
• 14. What if we removed this step entirely? Some of the best fixes eliminate a task instead of improving it.
• 15. What’s the worst possible idea, and what’s its opposite? Bad ideas lower the pressure and often reveal a useful reversal.

Prototype: 5 Questions to shape what you build

Prototype questions keep early builds cheap, fast, and focused on learning. A prototype is a rough version of an idea, such as a sketch, clickable mockup, or role-play, built to test one assumption.

Test: 5 Questions to ask users about a prototype

Test questions reveal how people actually use your idea, which is often different from how they describe it. Ask them while the person is using the prototype, not afterward.

Keep your own explanations to a minimum. If you need to explain the design, the design needs work.

• 21. What did you expect to happen when you clicked that? Gaps between expectation and result point to the most urgent fixes.
• 22. Talk me through what you’re thinking right now. Think-aloud comments catch hesitation that people forget by the end of a session.
• 23. What, if anything, felt confusing or slow? The “if anything” softener makes criticism feel welcome.
• 24. How does this compare with how you do it today? It anchors feedback to the user’s real alternative, not an ideal.
• 25. What’s missing that you expected to find? Missing items often matter more than flawed ones.

For structured task-based sessions, pair these prompts with a formal usability testing plan.

Iterate: 5 Questions to keep improving after launch

Iteration questions keep the design thinking loop running once a solution is live. They compare real behavior with your original assumptions.

How do you write strong how might we questions?

A “How might we” (HMW) question reframes a user problem as an open challenge the team can brainstorm against. According to Nielsen Norman Group, Procter & Gamble introduced the HMW template in the 1970s, and the design firm IDEO later popularized it.

Write HMW questions after your research, once the team agrees on its main findings. Then follow these steps.

1. Start from a specific insight.
   Use a finding from your interviews, not a general business goal like “grow revenue.”
2. State the outcome, not the solution.
   “How might we build a chatbot for billing?” assumes the answer. “How might we help customers understand their bill on the first read?” leaves room for many ideas.
3. Check the scope.
   “How might we improve healthcare?” is too broad to act on. “How might we add a blue button to the form?” is too narrow. Aim for a question that suggests several directions.
4. Phrase it positively.
   “How might we make users feel confident they have what they need?” beats “How might we stop users from calling us?”
5. Write several versions.
   Draft three to five HMWs per insight, then vote on the one that sparks the most ideas.

Which questioning techniques help you dig deeper?

Prepared questions only get you to the surface. Follow-up techniques get you to the reasons behind an answer, which is where most design insight lives.

The 5 Whys

The 5 Whys technique asks “why” repeatedly, usually about five times, to move from a symptom to a root cause. Imagine a software team hearing that new users skip onboarding.

1. Why do they skip it?
   It feels long.
2. Why does it feel long?
   It asks for setup details users don’t have yet.
3. Why don’t they have those details?
   The details live with their IT team.

Three rounds were enough here. The real problem is a missing handoff to IT, not a long tutorial.

Who, what, where, when, why, and how

This framework maps the full context around a problem. It works well in team workshops when the problem still feels fuzzy.

• Who: Who is affected, and who else is involved?
• What: What exactly happens, step by step?
• Where: Where does it happen, physically or in the product?
• When: When does it occur, and how often?
• Why: Why does it matter to the user?
• How: How do people work around it today?

Laddering and the power of silence

Laddering means building each follow-up on the person’s last answer: “You said it felt risky. What made it feel risky?” It moves the conversation from features to underlying values.

Silence is the simplest follow-up of all. Wait three or four seconds after an answer before speaking. People often fill the pause with the most honest part of their story.

How do you choose the right design thinking questions for your project?

Choose questions based on what you need to learn next, not on a fixed script. The table below matches common project goals to a starting question set and research method.

Most projects blend qualitative and quantitative work. For a refresher on which interview, observation, and community methods fit each stage, see this guide to qualitative research methods.

Design thinking examples: How questions shape real projects

The examples below are illustrative scenarios based on common project types. They show how the right question changes what a team ends up building.

Example 1: A US health system’s appointment scheduling

A regional health system saw patients abandoning online booking. The team’s first instinct was a cleaner booking screen.

Empathy research changed the direction completely.

• Question asked: “Walk me through the last time you tried to book an appointment.”
• What it revealed: Several patients stalled at the same moment because they didn’t know which visit type to choose.
• Resulting HMW: “How might we help patients pick the right visit type without calling the office?”
• Outcome: The team built a three-question triage step instead of redesigning the booking screen.

Example 2: A SaaS company’s onboarding drop-off

A software company noticed that trial users stalled on day two. Product managers assumed the problem was missing features.

• Empathize question: “What were you hoping to get done when you signed up?” revealed that most trial users wanted one report, fast.
• Define question: “What is the root cause, not just the symptom?” showed that the report needed data users hadn’t connected yet.
• Test question: “What did you expect to happen when you clicked that?” confirmed that a sample data set helped users see value before setup.

Example 3: An HR team redesigning new-hire onboarding

An HR team at a mid-sized company wanted to improve new-hire retention. Instead of asking “Did you like onboarding?”, they asked recent hires, “When did you first feel stuck, and who did you turn to?”

Answers clustered around week two, when formal training ended but managers assumed people were up to speed. The team prototyped a peer-buddy program and tested it with one department before rolling it out company-wide.

What mistakes weaken design thinking questions?

Most weak research traces back to a few repeated errors in how teams word or ask their questions. Watch for these before your next session.

• Leading wording: “Don’t you think this is easier?” pushes people to agree. Learn how to spot leading questions and rewrite them neutrally.
• Asking about the future: “Would you use this?” invites polite guesses. Ask what people did last time instead.
• Double-barreled questions: “Was setup fast and easy?” blends two ideas, so the answer is impossible to read.
• Pitching instead of listening: Explaining your concept for five minutes turns an interview into a sales call.
• Talking only to stakeholders: Internal teams know the business, but users know the problem.
• Jumping to solutions: Ideating before you define the problem locks the team into its first idea.
• Treating the guide as a script: The best insight often comes from a follow-up you didn’t plan.

How do you know your design thinking questions are working?

You can judge question quality by the answers they produce. Use these working benchmarks after each round of interviews or tests.

These are rules of thumb, not universal standards. Adjust them to your project, and record them so each round is comparable.

How QuestionPro supports design thinking research

Design thinking questions only help when you can ask them to the right people and act on the answers. QuestionPro lets teams run stage-matched research, from early interviews to validation surveys, without switching between disconnected tools.

• Empathy and testing sessions: QuestionPro UX supports live video interviews, unmoderated interviews, open-ended conversation tasks, image mark-ups, and video capture. You can recruit participants from demographic panels or invite your own customers.
• Ongoing co-creation: An online research community gives you a branded space for discussions, forums, and surveys with the same group of users. It suits the iterate stage, when you want to check ideas with people over weeks.
• Validation at scale: QuestionPro Market Research Software turns interview themes into surveys with logic and branching. Its analysis tools show how widespread each finding is.

This setup lets one team keep empathy notes, prototype feedback, and survey data connected. That makes it easier to trace each design decision back to a real user need.

Better design thinking questions start with curiosity

The best design thinking questions are simple, open, and asked with genuine curiosity. They focus on what people actually did, felt, and tried, rather than on what the team hopes to hear.

Start with five empathy questions, listen more than you talk, and let each answer shape the next question. Revisit your list at every stage. A question that worked during empathy research may be the wrong one during testing.

Frequently Asked Questions (FAQs)