The power of inquiry: how to ask better questions for improved outcomes -both for your personal and professional life-.

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By Maria Victoria De Santiago

October 3, 2022

The important thing is not to stop questioning. Curiosity has its own reason for existing.

Albert Einstein

The importance of questions has been pointed out since Socrates’ times. From Voltaire to Paul Samuelson, and from Einstein to Bertrand Russell, great minds have voiced their thoughts regarding this matter. Even Steve Jobs did, as Warren Berger points out in his book A More Beautiful Question. We’ll dive into an approach to the art of inquiry proposed by Berger in that book to leverage the power of questions. 

Questions are a great force of change, as they trigger creative thinking and enable the search for new solutions. They are, in fact, the cornerstone of innovation, science, and evolution itself.  Many great startups and products embedded in our daily lives, arose from one simple yet beautiful type of question: “What if …”. 

Questions have a catalytic quality — that is, they dissolve barriers to creative thinking and channel the pursuit of solutions into new, accelerated pathways.

Hal Gregersen, executive director, MIT Leadership Center

The power of inquiry has been acknowledged at this point. Yet, mastering the art of questioning remains yet another challenge. Many enemies and traps still hinder how we leverage this powerful tool and provocative art.

Among its barriers, conformity remains one of the most dreadsome of all. Gregersen, who has devoted himself to the study of questions, said that “the loss of creativity and an open mind may derive less from biological processes than from the cumulative weight of conformity.” Indeed, a great danger lies in the assumption that what you do, or more importantly, the way you do something, is the only way to do it.

A recent article from HBR also pointed out how “Critical thinking is about asking better questions”, while an older article from HBR delved into how good leadership is tightly linked to asking “good questions”. But how do we become better questioners? How do we build more beautiful questions? 

Warner Berger, inspired by The Design Thinking framework of work, proposes a three-step approach to making better use of the art of inquiry. Let’s dive into these 3 particular types of questions that build a framework for problem-solving.


Start with Why. And this is not, as Simon Sinek’s book proposes, to inspire others. It’s more related to questioning the status quo, to understanding the issue at hand. And it demands us to challenge assumptions of why a certain thing that seems to be a certain way cannot be different. Why can’t it be? Why does it have to be that way?

Similar to design thinking, you start by understanding the problem, and you dive into the challenge. This requires stepping back, gaining new perspectives, looking at an issue you’ve potentially taken as a given fact of reality from new angles to understand underlying assumptions, and uncovering what others might be missing by stepping back. 

Tip: You can always use tools like Disney’s Creative Strategy or the Six Thinking Hats to bring on different perspectives. But even if you resort to these tools, you’ll always be better equipped by listening and talking to people with different perspectives. Outsource new perspectives, talk to your team, bring on the perspective of people from other areas and diverse backgrounds, and even get thinking partners from outside your company. This will serve wonders to uncover that which others might have missed and will create wonderful ideation sessions when thinking about the next set of questions.


What if you proposed enabling new opportunities by posing “What if..” questions when looking at a problem or a challenge? “What if” questions propose building scenarios, changing context, and enabling possibilities. “What if we incorporated AI into our product?” “What if we used ML to accelerate our processes?” “What if plastic could no longer be used in our processes?” “What if we could start over?” “What if someone came from outside the company, what would they do in this situation? “

“What if” questions are vehicles for ideation processes and great triggers for brainstorming and drivers of new possibilities. This type of question enables divergent thinking. We use divergence to widen the scope of what could be done, to push ideas, and let wild approaches surface when searching for a solution. While building solutions, even digital products, is a wonderful tool if used correctly. 

Tip: Try the “think wrong” approach. Many creative personalities such as John Bielenberg, as well as creative firms such as Frog Design, use this to fuel divergent thinking. It encourages a wide range of ideas and particularly fosters wild approaches in the early ideation stages.
In “thinking wrong”, you try to come up with ideas that may not make any sense, forcing your brain out of the usual thinking paths, connecting the seemingly unconnected things, mixing and remixing unexpected ideas. From a neurological perspective, by exposing yourself to contrary thoughts you “jiggle your synapses” as Dr.Kathleen Taylor says.

One way to nudge neurons in the right direction is to challenge the very assumptions they have worked so hard to accumulate while young”.

K. Taylor. Quoted on Brains Inventing Themselves, by Conrad P. Pritscher


After diverging, it’s time to converge and start making decisions by narrowing down approaches so you can take action and explore how to do it. This is no easy stage -not that the previous ones were easy at all- but this is a stage when reality kicks in and things may not go as planned. This stage requires time, as the best way to understand how to do something,  is to test it. Learn by doing. There’s ample evidence that “there’s no substitute for quickly trying things out to see what works” as Berger says.

You probably are familiar with the spaghetti experiment. If not, check it out here.

The idea is to test rapidly in order to learn fast. This is an approach popularized in business environments by Ries with the minimum viable product (MVP) concept, but that actually applies to anything you are trying to solve in our current VUCA (volatile, uncertain, complex, and ambiguous) environment.  

Read more on what is the VUCA acronym, where it came from, and more: check VUCA World and an HBR approach here.

Building ideas, and testing out solutions should also be done in the search of:

  • validating approaches and methodologies
  • learning in each iteration and gathering feedback from others
  • testing the boundaries of what can be done

There are several ways to go about this, but the simplest one is to ask others about your idea. Try to gather insights from several sources and advisors regarding what you are endeavoring to build. But we’ve also seen this fail greatly for many now-successful start-ups and digital products. So, there is another vehicle: prototyping. 

“A prototype is a question, embodied.”

Diego Rodriguez, IDEO

Technology has enabled faster and easier prototyping, particularly for digital products. Prototypes today are more than just a sketch or a collection of screen designs. You can go as complex as you want with a wide variety of design and prototyping tools, as well as no-code and low-code solutions. 

Getting the idea into the physical world, materializing it into something people can better understand and even relate to, builds a much more compelling case. And, more importantly, allows for testing in a much more concrete and objective way. You’ll be able to gather insights and feedback with less bias, as you leave less room for your interlocutor to freely interpret.

(CAUTION! If you are running tests, be mindful of letting your product do the talking. Don’t over-explain or direct your user. It’s easy to conduct testing and generate bias without even noticing. Plan carefully.). 

The goal here, even when you fail, is to ask more questions:

  • Why did this idea fail?
  • Why didn’t the test result as expected?
  • How might we improve it?
  • Are we learning from our mistakes? How can we learn from this failure?
  • And always remember, even when you fail, to ask: What went well in this failure?

Questions are fundamental in our rapidly evolving world, where new possibilities are unlocked every minute with new and emerging technologies. The digital product landscape has shown that the boundaries of what can be done and what people value still have uncharted waters to explore. Questions can keep ideas moving forward, especially as the life expectancy of “answers” becomes shorter and shorter. 

It’s not about what it is, it’s about what it can become.

Theodor Seuss Geisel

This article is the first of a series of content regarding questioning and iconic question journeys. Stay tuned. 

Additional resources:

How Creative Leaders Tap Into the Power of Questions – IDEOU

Good Leadership Is About Asking Good Questions