The Art of Leading with Questions in UX Research

By Philip Burgess | UX Research Leader

When I first started as a UX researcher, I thought my job was to find answers. I believed that by asking direct questions, I could quickly uncover what users wanted or needed. But I soon realized that the real skill lies in leading with questions—not to get immediate answers, but to guide users into sharing deeper insights. This approach transforms interviews and usability tests from simple Q&A sessions into rich conversations that reveal what truly matters.

Leading with questions is an art that every UX researcher should master. It helps uncover motivations, frustrations, and behaviors that users themselves might not even be fully aware of. In this post, I’ll share how I learned to lead with questions, practical tips for doing it well, and examples that illustrate its power.

A UX researcher carefully listening and taking notes during a user interview

Why Leading with Questions Matters in UX Research

When you ask users direct questions like “Do you like this feature?” you often get simple yes or no answers. These answers rarely provide the depth needed to improve a product. Leading with questions means asking open-ended, thoughtful questions that encourage users to explain their thoughts and feelings.

For example, instead of asking “Do you find this app easy to use?” I learned to ask “Can you tell me about the last time you used this app? What was that experience like?” This invites users to share stories, which reveal context and emotions behind their actions.

This approach helps you:

• Discover hidden pain points users might not mention otherwise

• Understand the reasons behind user behavior

• Build empathy by hearing users’ stories in their own words

  
  

How I Learned to Lead with Questions

Early in my career, I struggled with interviews that felt like interrogations. Users gave short answers, and I left sessions with little useful insight. Then a mentor suggested I focus on how I asked questions, not just what I asked.

I started practicing:

• Using open-ended questions that begin with “how,” “what,” or “can you tell me about”

• Pausing after a user answers to give them space to add more

• Following up on interesting points with gentle prompts like “Can you explain that a bit more?”

  
  

One memorable session involved a user who said, “I don’t really use the search feature.” Instead of moving on, I asked, “What do you usually do when you want to find something in the app?” That led to a story about how the user preferred browsing categories, which revealed a navigation issue we hadn’t noticed.

Practical Tips for Leading with Questions

Here are some strategies I use to lead with questions effectively:

1. Start with broad questions

Begin interviews with general questions to make users comfortable. For example, “Can you walk me through how you usually use this product?” This sets the stage for deeper exploration.

2. Use silence as a tool

After a user answers, wait a few seconds before speaking. People often fill silence with more details or thoughts.

3. Avoid yes/no questions

Questions that can be answered with a simple yes or no limit insight. Instead of “Do you like this feature?” ask “What do you think about this feature?”

4. Follow up on interesting points

If a user mentions something unusual or emotional, ask them to elaborate. For example, “You mentioned frustration earlier. Can you tell me more about that?”

5. Paraphrase and confirm

Repeat what the user said in your own words to show you’re listening and to clarify meaning. For example, “So you find the navigation confusing because the labels aren’t clear?”

6. Use hypothetical questions carefully

Sometimes asking “What would you do if…” helps explore user expectations, but avoid overloading users with too many hypothetical scenarios.

Examples of Leading with Questions in Action

Here are two examples from my experience that show how leading with questions uncovers valuable insights:

Example 1: Improving an e-commerce checkout

A user said, “I usually abandon my cart.” Instead of asking why directly, I asked, “Can you tell me about the last time you tried to complete a purchase?” The user described confusion over shipping options and surprise fees. This led to redesigning the checkout flow to be clearer and more transparent.

Example 2: Enhancing a mobile app’s onboarding

A user mentioned, “I didn’t really understand what to do first.” I followed up with, “What was your first impression when you opened the app?” The user shared feeling overwhelmed by too many options. This insight helped simplify the onboarding process by guiding users step-by-step.

A UX researcher documenting user feedback on a tablet during a usability test

Building Confidence in Your Questioning Skills

Leading with questions takes practice and patience. Here are ways to build your confidence:

• Record and review sessions to notice how your questions influence user responses

• Role-play interviews with colleagues to try different questioning styles

• Prepare a flexible question guide but be ready to adapt based on user answers

• Reflect after each session on what worked and what could improve

  
  

Remember, your goal is to create a comfortable space where users feel heard and willing to share. The questions you ask shape that environment.

Final Thoughts on Leading with Questions

Mastering the art of leading with questions transforms UX research from surface-level data gathering into a journey of discovery. It reveals the stories behind user actions and uncovers opportunities to improve products in meaningful ways.

Next time you conduct a user interview or test, focus on how you ask questions. Start broad, listen deeply, and follow the user’s lead. You’ll find richer insights and build stronger empathy with the people you design for.