The Art of Questioning as a UX Skill

When starting any design project, you’ll have many questions on your mind. The problem you’re thinking about is not always the actual problem at hand. How can we get better at asking the right questions in order to solve the right problems?

I decided to brush up on my questioning skills by reading A More Beautiful Question by Warren Berger. Berger illustrates how questioning is an inherent skill we’re quite adept at during childhood. He notes that children haven’t developed a “mental model” of the world, so they question everything. But as we go through standardized education, we begin to suppress our curiosity.


As adults, it’s frowned upon to ask too many questions in the workplace. On the flip side, we’re often embarrassed when we don’t have immediate answers. But Berger claims the ability to admit you don’t have all the answers, but can ask better questions, is a superior skillset.

By analyzing innovative figures, Berger identified three common types of questions that lead to breakthroughs.

3 Types of Questions


Why does something have to be the way it is? Has everybody else missed something obvious? Are we basing our understanding on assumptions? Asking ‘why’ questions is about challenging assumptions and the status quo. A famous example of a ‘why’ question is when Edwin Land’s son asked, “Why do we have to wait to see our pictures?” Land answered that question by creating the Polaroid instant camera.

What if…?

This is where you mash up ideas, go against common logic, or add/remove factors that make the challenge more interesting. Sky’s the limit here as each wild idea often yields a workable element. This thought process is sometimes referred to as “divergent thinking.” Thank the candy gods that one day H.B. Reese, inventor of Reese’s Peanut Butter Cups asked, “What if you put peanut butter and chocolate together?”


This is where the rubber meets the road. Propose solutions, create testable hypotheses, perform a bunch of tests to gain insight. This is typically the “prototyping” stage where you have to see what elements of your ideas are compatible with reality. A near legendary example of the rapid prototyping is the story of the Google Glass team creating a working though ugly prototype of Glass in just 45 minutes.

Questioning in the Context of UX Design

So now that you know the basic framework for asking better questions, what questions should you ask and what assumptions should you challenge? As a UX designer and strategist, I often encounter clients who are in need of better problem framing and deeper insight before embarking on a design project.

A better understanding of the problem inevitably yields better solutions. Here are three statements I often hear from clients that are great opportunities for reframing through questioning.

Ex. 1 – We already know what our customers are like so we don’t need research or user testing.

Put more simply, clients often assume that they are exactly like their customers. An easy technique to challenge this assumption is inverting the statement. “We know our customers want to do XYZ…” becomes “How do we know our customers want to do XYZ? Why are they coming here in the first place?” When you invert your assumption statements, you can start the “Why” portion of the framework and challenge existing paradigms. Your goal is to derive solutions from a solid knowledge of underlying factors. From my experience, the “Why” is least clear to most clients and the most overlooked.

Ex. 2 – We think our customers need an app and we just need to partner with you to design it.

Before starting with a predetermined solution, teams should explore and exhaust the “What if” scenarios first. By removing constraints, teams can break out of their current paradigm and discover a more effective direction than the initial one. The “What if” phase is usually scary for established companies. But scrappy startups who are apt to try things that fly in the face of conventional wisdom have popularized the buzzwords “innovation,” and “disruption.”

Ex. 3 – Now that we’ve figured out the problem, we need to write detailed requirements and spend 3 months to build a beta.

After you determine a workable solution in the “What if” stage, the mindset of a team tends to latch onto a single solution. But the result of the “What if” stage is only a hypothesis, which still needs to be tested before committing resources. In the “How” stage, the team needs to maintain flexibility while focusing on creating shareable prototypes. Prototypes should be relatively cheap to create and thrown out quickly. A mantra of the lean startup movement is “fail faster.” It’s better to find the holes in your plan before doubling down.

Questioning in Business Culture

While most modern enterprise companies use buzzwords like “out of the box thinking”, they seem to rather question averse. Instead, they’ve created a culture which rewards employees on measures of efficiency, while punishing those who ask too many questions.

Enterprise software design treats the Lean method more as a process than a mindset. It’s used to move a project from concept to creation, but not to iterate and discover. In a true spirit of Lean, a team needs to be ready to try many approaches and fail. A strong culture of questioning is essential to achieving innovative results.

UX and product designers must adopt a questioning mindset. Skilled questioning leads to better outcomes and paradigm changes within organizations. You may stir the pot a little bit, but you may also help shape a new direction and encourage others to move forward.



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This Post Has 2 Comments

  1. Vicente Fernandez Reply

    Great article, Jason. Thanks for sharing your insight and for inspiring us to ask better questions.

  2. Andrea Sutton Reply

    UX teams have a great opportunity to facilitate problem solving in the product design business. The open ended question is one of the coolest devices they can use that drive solutions from a cross-disciplined group.

    When an entire team answers questions together, the team tends to take ownership of the results together — and that’s a huge win in the product design business. UX “questioning” techniques can galvanize team thinking. Better products result.

    Loved the article. Just wished you would build that prototype in 30 days, not 90. 🙂

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