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  • Daniel Ling

Warning: These 5 Questioning Types Could Elevate Your Design Thinker Status

Updated: Feb 13, 2023

Before the packed room of presidents, prime ministers, governors, and mayors- Greta Thunberg was livid. “This is all wrong. I shouldn’t be up here. I should be in school on the other side of the ocean,” she said. “How dare you pretend that this can be solved with just business as usual and some technical solutions?"

This is actually a fantastic Opening Question.

Let me explain- as we problem-solve in Design Thinking- the squad will have just spent weeks interviewing users, building personas, brainstorming for ideas, prototyping and then you realise that your solution does not work. Or worse, a boss or stakeholder points out an area you had not considered initially. Alas! You fret, you go back to the drawing board, you look through other possible ideas to test and you beat yourself up for taking the ‘wrong’ direction.

“I really should not have done that,” you would lament. In a world where so much focus is on doing and getting results, it is understandable that we have forgotten the value of thought and questioning. So perhaps, next time your work flounders, bemoan the fact that you did not ask that instead of you did not do that.

It takes the courage of Greta Thunberg to actually ask a difficult question that the rest are avoiding.

Questioning is crucial in every stage of design thinking. Be inquisitive and challenge yourself and your team by asking questions. However, do be conscious of who you are questioning and what you expect to elicit from their responses.

There are 5 different types of questions you can apply, primarily at the Define Phase of Design Thinking. Note that these questions are restructured differently from the kind you would normally ask users to discover insights. This will help you elevate yourself as a POWERFUL DESIGN THINKER.


Opening questions help us understand the context, assess the situation and gather thoughts and constraints that will set the design brief for the team. These questions will help define the problem statement. This is critical for the design team, as more often than not clients/bosses/stakeholders may approach you with an idea, a solution or even an ambiguous problem that may take the process away from users’ needs.

What is the problem we are trying to solve?

What are we looking at?

Why is this our focus area?


These questions will prevent project-derail if utilised in a timely manner. Navigating questions will help assess and adjust the course of the meeting, and therefore the project, among various stakeholders. Most importantly, it helps reduce meeting durations as everyone remains focused on the problem statement set earlier.

Did I understand this correctly?

Does anyone have any other questions?

Are we aligned in this?


These questions dive into project details. It quantifies and qualifies the product/ service that is being designed. At this stage, experts and specialised team members will be very handy in providing quick answers that will speeded up the process.

What is it made of?

What percentage increase in sales are we trying to achieve in 2 years?

Can you give me an example of this situation?


These questions, true to their namesake, exist to push the envelope. They consider the flip side of things, expand ideas and stretch your imagination. These questions can be very effective when evaluating ideas or brainstorming as a team.

What else could we use this for?

What if we did this using Plan B?

What is missing over here?


Closing questions, are an ideal way of ending an meeting. It breaks down the project into clear and realistic tasks and delegates responsibilities. Answering these questions will help you define your next steps and establish a clear action plan.

How can we prioritise these ideas?

What should we see in 2 weeks?

Who owns this task?

You are encouraged to use all 5 question types throughout your discussion in order to raise questions effectively. Bear in mind not to view yourself or anyone who raises questions as a roadblock, as the right questions, help define the problem more effectively, connect the team better, empathise with your stakeholders and reduce potential mistakes.

Last Words

I will be adding more articles on Design Thinking throughout the year. Articles of Empathize, Define, Ideate, Prototype and Test will be added periodically to give my readers a broader insights to Design Thinking.

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About the Author

Daniel Ling has more than 10 years of Design Thinking experience and has moulded himself to be a “designer in a business suit”- strong in the Design Thinking process and yet relevant to the financial and business industry- across OCBC, DBS, NTUC Income and Lazada. He trained close to 500 professionals in the area of Design Thinking, Innovation and Strategy. He authored the Complete Design Thinking Guide for Successful Professionals and the book is sold worldwide via Amazon, iTunes, Ingram, Lulu and Kinokuniya.

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