Earlier in the year, I was asked to do a short interview on what makes a great question.

I had so much fun answering that I wanted to share my thoughts on the topic here as well.

What Makes a Great Question?

1// Are there different question frames that affect what and how recipients will share? 

Design Questions

Designers always start with the famous “How Might We” question. This helps us to frame challenges in a way that leaves room for possibilities (might) and creates space for diverse opinions and collaboration (we).

While we have many methods for getting to our How Might We — like brainstorming or systems mapping — the best questions actually really come from curiosity, about people, and about the world at large. Conversations with others, walking down the street, or trying a new technology for the first time all spark curiosity about why things are they way they are.

• Why do people do the things they do?
• What are people saying vs. what they are actually doing?
• What re people thinking about, what are they worried about, what brings them joy?

These types of questions help us to stay interested and grounded in the here and now. By framing questions in this manner, we can start to get answers that map out systems, address people’s needs, motivations and pain points, and help us to gain a deeper understanding of what people really want, as opposed to what they say they want.

The answer to these types of questions are tools that help us ask better questions, or in reality, are a question themselves manifested through something touchable, e.g. sketches, designs, and prototypes are used to get feedback that helps us ask more specific questions about the problem we are trying to solve for, or even uncovers that the problem we thought we are solving for is not actually the right problem.

Eventually (in design there is no real ‘final’) you get to your most-complete prototype, your best answer and send it into the world as a product or service. Chances are it still isn’t done, and it will continue to generate new questions that cause it to evolve and change as the technology it is based on and the people who use it evolve and change as well.

Speculative Questions

Another type of question, speculative questions, generate completely different types of answers. These types of questions help us to look at the bigger picture and think about the future. Speculative questions start with What If, and the best speculative questions capture that provocation through a story or object that helps a user experience the future represented it comes from.

As opposed to design questions like How Might We, speculative questions situate us in the future, helping us to imagine what the world might be like, what future we want, and what it might feel like to live in a future where today’s STEEP (social, technological, ecological, economic, political) forces play out in different ways.

I believe that the strongest Speculative questions help users to achieve what Speculative Fiction critic Darko Suvin calls “Cognitive Estrangement” – what happens when a story, design, or object forces us to imagine a new and different way of conceiving the world. For Suvin, this was the whole point of science fiction, stories that make us consider alternate realities and futures that directly contradict today’s status quo. This is especially powerful for marginalized communities who don’t often see themselves reflected in many stories about the present: women, people of color, and queer/trans people.

For this reason, I believe that speculative practice (whether fiction or design) is asking some of today’s most high-impact questions, those that cause humans to realize that many of the norms and things we take for granted in our society are actually 100% changeable. Speculative questions are important because they lead us to ask better, deeper, more informed questions that help us to address our unarticulated assumptions about the way things really are today, and to better consider the ways things could be tomorrow if such and such were different.

2// In your experience as a designer, what are you some of the questions you find yourself asking again and again? 

As I mentioned earlier, designers always start with brainstorming, remixing, and merging questions into a How Might We as a way to frame out our design challenge. These questions allow us to understand what information we need to research, what prototypes we need to create that can answer our questions/test our assumptions more deeply, and who needs to be at the table to help answer those questions.

But, in reality, the question I would say that I truly ask the most as a Designer is simply “Why?”.

Design Thinking can be applied to any question or problem, whether or not it is ‘design’ related. Asking business partners, stakeholders, and users Why helps to get them to get to the heart of the problem, and hopefully consider their unquestioned assumptions.

• Why do we use this system?
• Why aren’t our users interacting with X, Y, Z like we predicted?
• Why do people like to come to our site every Wednesday at 6:17pm sharp?
• Why, why, why.

In fact, in Design we actually borrow a research tool created by Sakichi Toyoda of Toyota Motor Corporation during the evolution of its manufacturing processes. It’s called the 5 Whys.

First you ask a question or state a problem. Then you ask Why 5 times. Usually 5 times is enough to help you get to the root cause of a problem. Each why forms the basis of the next question. The goal is for the final Why to point to a process or problem that is not working well or doesn’t yet exist. Thus a great place for a design intervention.

3// What’s the relationship between questions and decision-making?

Many people think that Designers job is to look for solutions to problems that our users have, or those I anticipate they will have. But the truth is, being a designer is actually breaking yourself of the habit to be reactive to the problems in front of you, and instead forcing your mind to relax, step back, frame your question, do research, analyze your answers, and let new questions emerge. You have to surrender yourself to the iterative design process, which isn’t naturally how humans make decisions about how to solve problems. 

For example, when my a pipe in my Kitchen breaks, I don’t sit there pondering, well what is the right question? How might I re-engineer my plumbing so that I don’t need pipes? Let me interview some people about their pipes, or watch a plumber purchase and install pipes, or research the history of pipe systems, why they are they way they are, and why they break.

No, I freak out, try to figure out why the pipe broke as quickly as possible, and figure out a solution before my kitchen floods.

I think the relationship between questions and decision-making is to allow yourself the time and research to find the right question, using your designs and prototypes as research, as questions, to help you generate new and better questions until you get to the one that really has to be answered. Then, and only then, should you start trying to figure out potential solutions. Chances are, the first solution isn’t quite right, or is temporary, since technology is changing constantly, but you can make the best decision for what is right in the here and now and stay open the fact that the answer today might not be the right answer tomorrow.

The same thing goes for speculative questions. Big ‘Wicked’ challenges like climate change, discrimination, and education inequality don’t have easy answers, and there is certainly no catch-all question that can capture the intricacy of the forces at work. For these types of questions, it’s even more important to give yourself over to the process and collaborate with others to continually ask new questions and share your provocations to open up new spaces for debate and critique. 

Speculative questions are more about curating than creating.

Collecting and curating your own ideas and curiosity into a meaningful presentation that communicates your provocation to others in the right way is no easy task. For this reason, the sweet spot in Speculative Design is actually ambiguity. Your provocation, regardless of the medium, shouldn’t provide the audience with easy answers, it should entice them to pull closer and ask questions about how it works and what it means. They should question how they assume it works, what it does, and what futures it opens up or closes down in its creation. By provoking users to feel a bit uneasy, neither sure if its good or bad, it entices them to debate, critique, and learn more about the topic you are conveying, and in turns helps them to ask better questions and make better decisions about the future that they want. This type of provocation engenders agency, empowerment. The ability to even ask constructive and informed questions about the future.

4// How do we get better at asking questions and making decisions?

At the end of the day, I think we all can do three things to become better question-askers and decision-makers.

1. Pay Attention – Look for information from a variety of sources, stay speculative and consume stories and projects that provoke speculation. Don’t dismiss things as folly, fancy, or fiction. Stories are very powerful mechanisms for provoking new ways of seeing the world from a different viewpoint.
   
2. Make Sense of What You are Paying Attention To – Build your sense-making muscle to help you connect and understand what it is you are learning about, what is happening, and what it means. Learn to ask questions about what you hear, read, and see. Use tools like signal-scanning, systems mapping, trend analysis to help connect the things you notice into a more robust understanding.
   
3. Tell Stories – Don’t just keep your questions to yourself, share your provocations! Diverse opinions are important and usually you find the best new insights from teaching or explaining your ideas to other people.

5// How does a poorly framed question impact the future?

The paradox of science, and thereby technology, is that all the answers we reach breed more questions. The more disruptive the technology, the more disruptive the questions. Right now technologies like AI, blockchain, bio-tech, and the IOT/Smart city are creating huge questions we never thought to ask before, perhaps some of our biggest questions yet. 

• What if we can design our own DNA in the future to eradicate birth defects, pick gender, provide biological enhancements?
• How do I know the answers my computer assistant gives me are true?
• What is truth when so many differing points of view exist about the same event? Which truth do I trust?

We need to be extra careful about observing technology and the changes it has the potential to create in our society, continually asking ourselves, is that the future we want? No, then what future do we want?

If we can’t frame critical questions about today’s emerging technology, explain them in terms people understand, and collect their diverse feedback, than we won’t be able to have future-agency, the agency to define and design the future that is preferable for as many people as possible.

6// Do you believe that as a culture we are moving away from or towards asking and rewarding those who ask high-impact questions?

I remember sitting in the back of my friends car in 2009 and driving around Long Island not doing much of anything, our normal activity as young 20-somethings. As usual, I asked some ridiculous question not expecting an answer, but more of a provocation to my friends. But this time, instead of debating and wondering about the answer (before we went home and checked online), my one friend pulled out her new iPhone and looked up the answer on the spot. I remember being absolutely floored, and saying, “You know this changes everything?”. And it did.

Every day our technology gets better at answering our questions more rapidly, accurately, and contextually. We have Google Assistant, Siri, Alexa whispering answers to our most banal (or existential if you want a laugh) questions on-demand, if those questions have recorded answers. One day soon, we will be able to ask any question conversationally, and have our technology answer us at a fair-approximation of a human response. 
But what if the question doesn’t have an answer? What if that answer is influenced by which technology we are using, who controls the network, and our many collected preferences and personal choices that influence the content we see?

While technology might have ‘easy answers’ it is crucial that we think about where those answers are coming from, who created them, and how they may be colored by our own unique digital signature and resulting user experience. Is the answer tailored just for us?

Our job as humans, more and more, will be to learn to ask good questions, and not blindly rely on our technology for quick easy answers. Great questions don’t just provide an answer, they provoke us to ask better related questions that help us to generate new ideas and innovations. 

On one hand, I think that we as a culture are moving towards a post-truth, post-fact era, where paradoxically its becoming easier and easier to get an answer to our every question, yet harder and harder to trust or rely upon the answers provided without a high-level of media-literacy. This accessibility paired with mistrust can make it seem like we are moving away from asking and rewarding those who do ask high-impact questions, since its so much easier to get the instant gratification of quick answers, regardless of their veracity. 

As such, we need to focus on educating people to discern truth, follow-up on sources, and understand how their technology works. Only then can we understand how the answers we are provided with are shaped and what biases they have, becoming better sense-makers in a Volatile, Uncertain, Complex, Ambiguous (VUCA) world.

On the other hand, I have noticed that asking high-impact questions is becoming more important across a variety of fields.

The whole idea of ‘speculative’ practice, whether it be design, fiction, architecture, ethnography etc. is to ask questions, to speculate on potential futures that emerge from the seeds of the social, technological, economic, environmental and political forces today. When I first heard of Speculative Design in 2015, it was quite hard to find resources and communities of practice to join.

I’m excited that now, more and more individuals, educators, and organizations are encouraging speculative design and strategic foresight techniques such as future-casting, speculative prototyping, world-building and storytelling all founded on my favorite question of all, “What If”.

And… that’s all folks!

Learn more about why I think it is important to Stay Speculative in my recent article!