Dr. Craig Wing: What if we valued questions more than answers?

In this episode of Impact Stories, Ronny Eriksson interviews Dr. Craig Wing, a futurist, entrepreneur, and investor whose expertise spans over 50 countries and influential organizations like Google X and the United Nations. 

Dr. Wing unpacks the profound question, “What if we were all more capable of imagining the future?” He explores how imagination, empathy, and human connection can reshape our lives and influence the world in more impactful ways. From advancing AI sentiment analysis to fostering inclusive thinking, Dr. Wing’s work challenges us to consider the future as a collective endeavor. 

Listen in to discover how small, meaningful actions contribute to greater change and why sometimes the best impact begins with asking better questions.

Transcript

Ronny Eriksson: Welcome to the podcast, Dr. Craig Wing! With us, you're not just a listener—you’re part of the community and the movement driving real progress. Let’s explore how big ideas can turn into real-world positive impacts together. Dr. Wing, you've helped thousands of global leaders and executives craft their ideal futures through imagineering and future think. You even have a PhD in this, which led to a startup helping organizations understand how they can succeed in the future. Your work spans over 50 countries, and you've consulted for companies like Google X and the United Nations. You’ve also founded four companies, secured patents for disruptive technologies, and actively invest in innovative startups. It’s a pleasure to have you here today.

Dr. Craig Wing: Thank you so much, Ronny. It’s an honor to be here, and I appreciate that warm introduction.

Ronny Eriksson: Each episode, we start with a big "what if" question. This time, it's one I think you'll appreciate: What if we were all more capable of imagining the future?

Dr. Craig Wing: That's a great question, and one that touches on so much of what I believe. If we were all better at imagining the future, I think the world would be more tolerant and understanding. We all carry biases—biases built into the ways we were raised and the experiences we’ve had. As we grow older, our perspectives tend to narrow, creating certain pathways or mental models that become our standard way of thinking.

There's a quote I love by futurist Alvin Toffler, who said, "The illiterate of the 21st century will not be those who cannot read or write, but those who cannot learn, unlearn, and relearn." Imagination is at the core of that. If we could imagine a more tolerant society, one that’s able to see the world from others’ perspectives, it would be a big first step. That’s why events like Katapult Future Fest are so valuable—they push us to think beyond our usual frameworks.

I also think if more people embraced imagination, we'd have a more humane world. In a time dominated by technology—AI, machine learning, you name it—there’s a growing need for a humanistic perspective. AI, as advanced as it is, is still just a statistical machine. It gives you the most likely answer, not the true one. Yet society increasingly treats people like machines, especially in systems that prize efficiency over creativity.

There was a fascinating study in April 2023 comparing doctors and a chatbot’s responses to medical queries. People overwhelmingly rated the chatbot as more empathetic. Some argue this means AI will take over jobs, but I see it differently: we need more human empathy, not less. Imagination and empathy go hand-in-hand.

Ronny Eriksson: You touch on a critical point. We talk a lot about creativity, and it seems the most creative individuals are the ones who can see things that don’t yet exist. Artists, musicians, writers—they’re skilled at putting abstract ideas into tangible forms. Why do you think this type of imagination is often missing in everyday life?

Dr. Craig Wing: Great question. It really comes down to how society is built. If we look back to the Industrial Revolution, we see that work was designed around efficiency and repetition. The entire assembly line model was about minimizing deviation, not encouraging creativity. And this mindset extended to education, which prepared people to fit into that assembly line.

Now, with the rise of technology, we’re stuck between two competing forces: on one hand, society’s foundational systems still expect people to function as cogs in a machine. On the other, technology is pushing us to think differently, but only in a way that serves existing frameworks of productivity and profit. True imagination, which doesn’t always yield a measurable outcome, gets squeezed out.

Ronny Eriksson: So, how do we break free from these patterns? How do we get people to imagine a better future when they’re so ingrained in the systems you just described?

Dr. Craig Wing: One part of the solution is to challenge the assumption that the future is merely an extension of the past. Most businesses and people make decisions based on past data, assuming that what worked before will work again. This kind of linear thinking limits us. Look at what happened with COVID: companies that relied on extrapolating past trends were blindsided. My PhD research actually explores this—how to prepare for what I call “winter futures,” or scenarios where the past provides no roadmap for the future.

Ronny Eriksson: Interesting. Could you elaborate on “winter futures”?

Dr. Craig Wing: Absolutely. “Winter futures” comes from a two-by-two matrix I developed based on Johari’s Window and Donald Rumsfeld’s concept of "unknown unknowns." Imagine a world where we don’t know what’s coming. It’s like in Game of Thrones, where everyone is focused on their battles and politics, but the real threat is this army of white walkers across the wall. “Winter futures” represents that kind of existential risk—the unknown factors that could fundamentally change everything.

In this context, the “what if” question isn’t just about asking how to improve something we already know; it’s about considering possibilities we haven’t even imagined. It’s challenging, but it’s essential if we want to prepare for true transformation.

Ronny Eriksson: That’s a fascinating perspective. So, would you say the focus shouldn’t be on answering questions, but on asking the right ones?

Dr. Craig Wing: Exactly. Society rewards answers, especially in business. But sometimes, having the right question is more important than having an answer. Theoretical physicist Richard Feynman once said, “I would rather have questions that can't be answered than answers that can't be questioned.”

Many of the challenges we face today stem from people focusing on answers without asking whether they’re addressing the true issue. Think about political manifestos, for instance—they’re often filled with answers but rarely do they address the underlying problems. We need to stop settling for easy answers and start asking better questions.

Ronny Eriksson: Some organizations, like Google X, really encourage this type of thinking. But for most, it’s a foreign concept. How can we make this approach more accessible?

Dr. Craig Wing: It starts with curiosity—something we often lose as we get older. Instead of rewarding people for having the “right” answer, we should reward them for their willingness to ask questions and challenge assumptions. Creating incentives around this kind of thinking can shift mindsets. We also need to make time for reflection. So few leaders actually schedule time to think. It’s astonishing when you ask executives how much time they set aside just to reflect.

Curiosity, time for reflection, and an openness to diverse perspectives—these are the building blocks for a more imaginative society.

Ronny Eriksson: It sounds simple but makes a lot of sense. So here at Katapult Future Fest, what kind of impact are you hoping to make?

Dr. Craig Wing: For me, the goal is to create “incidental occurrences”—chance encounters that lead to meaningful connections. Some of the best things in life come from serendipity. It’s not always about having a specific agenda; it’s about being open to whatever opportunities come your way. Being present, having conversations, and just seeing where things go.

Ronny Eriksson: That’s a beautiful way to look at it. It’s often in those unexpected moments that the biggest ideas emerge.

Dr. Craig Wing: Exactly. We tend to overlook the importance of being human in a world that increasingly pushes us to act like machines. Human connection and curiosity are the foundations of imagination and innovation. If we lose that, we lose the essence of what makes us capable of creating a better future.

Ronny Eriksson: If you had one piece of advice for someone looking to make an impact, what would it be?

Dr. Craig Wing: Impact doesn’t have to be massive. It can be a small act of kindness—opening a door, offering a smile. True impact is measured on a micro level. Sometimes the most significant impact you can make is making one person’s day a little better.

Ronny Eriksson: Thank you so much, Craig, for sharing these insights. It’s been an inspiring conversation, and I can’t wait to see what you do next.

Dr. Craig Wing: Thank you, Ronny. It’s been a pleasure.