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10 minute read

Great Questions Lead to Great Design – A Guide to the Design Thinking Process

Jorge Juan Perales

Jorge Juan has designed successful digital products for over a decade. He loves fast-moving teams and delivering great value to users.
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30/04/2019 Design Thinking – Great Questions Lead to Great Design | Toptal
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Read the Spanish version of this article translated by Yesica Danderfer

Great designers help teams and stakeholders make better decisions by using questions to identify opportunities, reveal underlying needs, and understand
user context.

James Dyson, having been inspired by a centrifuge used to separate paint particles from the air, came up with the world’s first bagless vacuum cleaner in 1983 after
famously going through 5,127 prototypes—the epitome of design thinking. He must have asked a lot of questions along the way…

Designers face tough problems every day—problems that require them to find design solutions that deal with business and technical constraints while also addressing
user needs. At the same time, the urge to find solutions quickly shouldn’t preclude designers from thoroughly understanding the heart of the problem, as well as the
user context, from the outset.

The critical “investigative phase” should not be bypassed—it is a vital component in the design-thinking process. It is where carefully formulated questions reveal
themselves as a great way to approach a design problem even before designers start “designing.”

Questions are a genuine expression of our curiosity and interest in something. They are the means by which people seek meaning in the surrounding world and often
trigger our willingness to explore.

When designers are faced with a problem, their brain is programmed to find a good enough solution right away and act upon it. However, it is important to note that
those willing to deliver successful products and services must face the problems and build a deeper understanding of them in order to come up with valuable insights.

By knowing how questions work and how to use them cleverly, designers can unleash the potential of good questions to build understanding, trigger the imagination,
and foster collaboration.

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Why Designers Don’t Ask Questions

Designers typically operate in fast-moving environments which demand focusing on quick solutions and delivery. In that context, questions like “Why do we need
to solve that problem?” or “How did you notice this problem?” which may lead to a better understanding of the underlying causes and needs, are seen as
interruptions that slow down the process.

While quick wins are OK in some situations, designers also have the responsibility to help teams establish direction and not waste valuable resources working—no
matter how fast—on the wrong problems.

Designers are like detectives; they need information from many different sources in order to resolve their cases. And what is a key skill that good detectives have?
Asking smart questions that help them clarify the case, solve the puzzle and find the truth.

Why Don’t Designers Ask Questions as Often as They Should?

Some designers are afraid of annoying people. When someone presents a new idea or solution to the team, questions that reveal weaknesses or uncovered areas can
make owners feel uncomfortable. They thought they had it all figured out, and suddenly, there’s an element of uncertainty introduced into the picture.

They realize there is more to think about than they had expected, so they look at the designer as an “annoyance.” Designers should make it clear that they are not
there to annoy people or slow down the process unnecessarily but to help the team build better products; consequently, their feedback should be seen as a valuable
contribution and a crucial part of a prudent design process.

A lot of people think of designers at an execution level—decisions are made by technology, business, and marketing teams while designers are there to simply
execute commands. But designers also have the responsibility to expose the value of design at a strategic level.

Some designers lack the confidence and training—both to ask good questions and to do it in a way that clearly reveals their will to help and collaborate. As
everything in life, asking good questions is a matter of training. The more you do it, the better you get at it. One of the purposes of this article is to provide designers
with some ideas that will help them get started in the art of asking good questions.

Types of Effective Questions for Designers

A good question is the one that lets you obtain the type, quality, and quantity of information you need. In order to do so, designers have to decide both the type of
questions they use and the way they formulate them.

Here are some basic but very effective types:

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Open-ended questions encourage people to reflect and reveal what’s important for them. They allow people to freely expand on what is comfortable for them, rather
than justifying their thoughts. Open-ended questions tend to explore possibilities, feelings, and the reasons why. Michael J. Marquardt, author of Leading with
questions, describes some types of open-ended questions:

Explorative questions force expansion on new points of view and uncovered areas. Have you thought of…?
Affective questions reveal people’s feelings about something. How do you feel about…?
Reflective questions encourage more elaboration. What do you think causes…?
Probing questions invite a deeper examination. Can you describe how…?
Analytical questions look for the roots of a problem. What are the causes of…?
Clarifying questions help align and avoid misunderstandings. So, you mean that..?

Closed questions call for specific answers—usually yes or no—or they force the respondent to select an answer from a given set, or to agree or disagree with a
statement. Closed questions tend to focus on facts—what, when, where—and are usually easy to answer. For example: “Where were you born? How many miles do
you drive a month?”

The Anatomy of a Good Question

A good question doesn’t depend just on the type of question it is, but also on how you frame it. The form of a question is part of its function. Good questions should
be framed under these principles:

Good questions should empower. Disempowering questions focus on why the person did not succeed, which puts that person in a defensive mode. Empowering
questions are asked from trust—they get people to think and find their own answers, which transfers ownership and develops self-responsibility.

For example, when giving feedback, instead of just saying “I don’t think this would work,” you could ask, “What other options have you explored, and why did you
choose this one?”

Good questions should challenge assumptions. They should help clarify the situation and cause individuals, teams, and organizations to explore the methods,
processes, and conventions that drive their actions.

Good questions should cause the person to stretch. They should encourage reflection and help people go beyond the obvious. Good questions motivate people to
take things to the next level. For example, when discussing with technology teams, instead of asking, “Can you do this?” you could ask, “Supposing this is the way
to go, what would you need to have or eliminate in order to accomplish this?”

Good questions should encourage breakthrough thinking. Good questions open up new possibilities. They involve people in divergent thought processes that lead
to new perspectives. For example, when designing a new login screen, instead of just asking, “How could we make the login process faster?” you could ask, “How
could we deliver value to our users without them having to log in?”

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The Setup for Good Questions

Even if you choose the right type of question and you frame it correctly, you need to set the stage in order for others to understand why you are asking questions and
what for. Designers are not judges—they are facilitators that provide a context for the information to flow as part of the design thinking framework and help everyone
make informed decisions.

Here is a process that helps accomplish that:

Adopt a learner mindset. Our mindset frames how we see the world. A learner is optimistic and seeks understanding as a way to guide their actions. Be curious,
attentive, and receptive. You are not a judge, you are a designer who needs to investigate the problem more deeply in order to make decisions, so let people know
that.

Find the right people to ask. Learn who can help you the most and be sure you can count on them: adapt to their schedule, look for the best moment to get them on
board and engage them in your project.

Set the stage. Warm up. Provide context and get people to feel comfortable in order for them to be open and ready.

Ask your questions. Sometimes, you just want people to express their thoughts on something. Other times, you want to ask specific questions even if you know it
will be unpleasant for them. If you really need answers to those, set the stage properly and ask them anyway.

Dig deeper. Ask follow-up questions in order to get deeper information and clarify that everyone understands the same thing. Use the power of silence—just keep
silent, look people in the eye, and nod—so they can expand on their thoughts and ideas without interruption.

How Can Asking Good Questions Build Understanding?

Good questions challenge the status quo, forcing people to pay attention to what’s really going on. They help discover how things work, who’s involved, and how
everything relates. Questions help create a clear map of the situation.

Find the root of the problem. Some designers focus on symptoms and simply provide solutions for them. Great designers focus on understanding the origin of those
symptoms in order to make a good diagnosis.

Challenge assumptions. Individuals, teams, and organizations have their own habits and processes. Good questions help detect their biases and find new
perspectives and points of view.

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Understanding context. Designers use different mapping techniques in order to get a clear picture of how the whole system works. They use ethnography and
empathy to understand people’s behaviors and mental models. Good questions help gain valuable insights and uncover social, economic, or cultural patterns that take
place in a particular context.

Questioning Techniques That Build a Deeper Understanding

The 5 Whys

This method helps you get a deeper understanding of the root causes and underlying beliefs and motivations of people. It’s at the heart of a proper design thinking
process. Sakichi Toyoda, one of the fathers of the Japanese industrial revolution, developed the technique in the 1930s. Here’s how to apply it:

1. People don’t buy products in our online store. – Why?

2. Because they don’t complete the purchase, they drop off. – Why?
3. Because they tend to abandon the shopping cart. – Why?
4. Because the cart is where we show shipping details and they think 10 days is too long. – Why?
5. Because people buy our product as a gift to someone just a couple of days before the gifting date. 10 days is too long for shipping.

By question five, product designers most likely got closer to the root of the problem and shed light on new approaches to consider that weren’t necessarily the
original, “assumed” problem. For a deeper description on the 5 Whys Method, visit Mindtools.

Who, What, Where, When, Why, and How

This is another framework that can be used in order to analyze and get a deeper understanding of the situation and context. Whenever you face a problem, asking
these questions will help you get a clear view of the current situation, map critical pain points, and come up with possible ways of taking concrete action that will
solve the problem:

Who interferes with the process in the situation? Users, stakeholders, suppliers, clients, team…
What elements compose the situation? Actions, behaviors, elements, tools…
Where does it happen? Geographically, culturally, socially, economically…
When does this occur? Past, present, future, situational context (when I’m in a rush), frequency…
Why does this happen? Causes, constraints, needs, motivations…
How is the situation created? Processes, metrics, results…

How Can Designers Trigger the Imagination by Asking Great Questions?

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Great questions have the power to transport us to unimagined scenarios and transform the way we see reality. Questions like, “How would this be in 2050?” lead us
to a mindset where our current constraints and biases are no longer valid, forcing us to operate under new paradigms.

When we reframe a situation with questions like, “What would happen if all humans were blind?” we are challenging the set of beliefs and values that we use when
inferring meaning, so our view of the situation can change dramatically. When people see things from new perspectives, innovation happens.

Questioning Techniques That Can Trigger the Imagination

There are some question starters that will help you frame your questions in a way that encourages imagination and causes people to develop new perspectives:

What if…?
How would it be different if…?
Suppose that…?
What if we knew…?
What would change if…?
What other way could we…?

How Can Designers Foster Collaboration by Asking Great Questions?

Questions are also a good way to help teammates identify critical points in their designs and find stronger arguments for their decisions. Through intelligent and
constructive feedback, the whole team can benefit from everyone’s point of view and area of expertise.

Instead of asking “Isn’t that interaction a bit awkward?” which could make people defensive, great designers ask questions like, “What were other options you
considered, and why did you choose this one?” You’ll help people reflect on their work, explain the reasons why, and see questions as a gift.

Questions build respect and show interest in others’ feelings and thoughts. They help align team members, clarify goals, and give people a sense of responsibility
and ownership.

Questions also improve self-awareness and develop better listening and greater understanding capabilities. When you ask your teammates questions, you learn about
how they think, what they believe in, how they feel in certain situations, etc. It helps build solid links with the team.

Questioning Techniques That Foster Collaboration

As part of a design thinking exercise, there are some question starters that will help frame questions in a way that builds trust and encourages team collaboration:

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How do you feel about…?
How would you describe…?
How could we…?
What help do we need in order to…?

The Design Thinking Process Using Great Questions

Questioning is a powerful tool that every designer should be able to use fluently. As part of a design thinking process, questions can help understand a situation and
get valuable insights. They can also foster creativity and innovation within an organization, and can help teams align and unite.

Asking questions and letting the information flow is essential for growth as an individual and as an organization. But a questioning culture also requires an
atmosphere of trust and responsibility, where everyone’s wisdom and capabilities are respected and promoted.

As a designer, ask questions and make sure everyone understands that they come from genuine curiosity and a desire to explore product design more deeply, with the
aim of coming up with the best design solution.

•••

Further reading on the Toptal Design Blog:

UI Design Best Practices and Common Mistakes
Empty States – The Most Overlooked Aspect of UX
Simplicity Is Key – Exploring Minimal Web Design
Heuristic Principles for Mobile Interfaces
Designing for Readability – A Guide to Web Typography

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Jorge Juan Perales

Designer

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About the author

Jorge Juan has more than a decade of experience designing successful products from concept and MVP definition to prototypes and high-fidelity visuals. A creative,
detail-oriented, and strategic thinker, he loves to work in fast-moving teams and create products that deliver great value to users while incorporating technical
capabilities and business goals.

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Jonny Bobgan • a year ago

“Good questions should empower.” I love this statement! All around a great article. As someone who works regularly with lower-budget clients,
there's often “streamlining” in my process to land within the budget. I like to tactfully remind my clients that I owe it to both of us to be curious and
forward with my questions and suggestions for exploration. I’ve found the majority of my questions are met with gratitude even when I know I’m
raising a flag that might halt or slow our progress. Rarely have my clients not been willing to approve some extra time to ensure we are asking the
right questions to solve the right problems.
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