Asking the Big Questions

How the biggest questions can unlock the deepest insight

"What is the origin of the universe?"

I was fourteen, sprawled on the couch after watching Carl Sagan's Cosmos, and my mind was utterly blown. This question consumed me—not just for days, but for months. Looking back, I realize why I was so obsessed: at the time, this was the biggest question I could think of. And that realization sparked something fundamental in me—an innate desire to always ask the biggest possible question in any situation.

That one question set me on a meandering intellectual journey. From the origin of the universe, I dove into relativity (which, honestly, I still don't fully comprehend), then black holes, then time travel. The twin paradox—where one brother travels at near light speed while the other stays on Earth—became my favorite thought experiment. I'd test it on friends, watching their faces light up as they grasped the implications. Eventually, I created a PowerPoint deck about time travel. I took it on a speaking tour across high schools and astronomical societies—basically anywhere people would listen to an enthusiastic teenager talk about the fabric of spacetime.

This journey ultimately led me from cosmology to engineering, then to artificial intelligence, and eventually to philosophy. Each step was driven by asking: "What's the biggest question here?"

A Warning and a Reflection

Before I go further, I want to be upfront: this isn't a how-to article. It's a reflection on how my brain works. If you're looking for a step-by-step guide, you might be disappointed. But if you're curious about how asking big questions can shape your thinking and lead to unexpected breakthroughs, then read on.

The Power of Big Questions at Any Level

One thing I've learned is that you don't need to ponder the universe's origin to benefit from asking big questions. You can apply this approach at any level of your life—from choosing a restaurant with friends to designing a product strategy.

If you and your friend always end up at the same restaurant, asking "Why do we keep coming here?" might lead to "What do we actually value in our dining experiences?" And suddenly you're exploring new neighborhoods and cuisines. At work, when everyone's focused on feature improvements, asking "What problem are we really trying to solve for customers?" can shift the entire product direction. The key isn't the cosmic scale of the question—it's asking the biggest possible question appropriate for your context.

Frameworks for Asking Big Questions

While my journey has been meandering, I've discovered several frameworks that codify this approach. These aren't rigid methodologies but flexible tools that help create space for deeper inquiry:

The 5 Whys

This classic technique from Toyota's production system pushes you to ask "why" five times in succession to get to the root cause of any problem. The brilliance lies in its simplicity.

Let's say your product team is consistently missing deadlines. Why? "Because we keep discovering new requirements late in development." Why? "Because we don't fully understand user needs upfront." Why? "Because our user research is rushed." Why? "Because we're under pressure to start building quickly." Why? "Because leadership measures us on speed to market, not product-market fit."

Notice how we went from a surface problem (missing deadlines) to a fundamental strategic issue (misaligned incentives). The first why gives you a symptom. The fifth why often reveals the fundamental issue worth solving. I've found this particularly powerful in product strategy sessions where everyone thinks they know the problem, but no one has asked enough whys to be sure.

"How Might We" from Stanford d.school

This framework, popularized by Stanford's d.school and IDEO, transforms constraints into creative opportunities through the power of reframing.

The magic is in the three-word structure. "How" suggests possibility—we don't know the answer yet, but there is one. "Might" creates permission to speculate and take risks—our ideas might work or might not, and that's okay. "We" builds collaborative ownership of both the problem and the solution.

Instead of saying "We can't afford to redesign the interface," try "How might we improve user experience with our current resources?" The first statement shuts down thinking. The second opens it up. Suddenly, you're brainstorming micro-interactions, better copy, simplified flows—solutions that don't require massive engineering effort.

I use this framework when I catch myself or my team making definitive statements about what we "can't" do. Almost always, there's a "How Might We" question hiding underneath that unlocks creative solutions.

Zoom Out, Zoom In by John Hagel

Sometimes the biggest question requires movement between different altitudes of thinking. John Hagel's framework recognizes that breakthrough insights often come from oscillating between the macro and micro perspectives.

Zoom out to see the entire landscape—market trends, customer ecosystems, competitive dynamics, and technological shifts. At this altitude, you might ask: "How is the fundamental nature of our industry changing?" or "What job are customers really trying to accomplish?"

Then zoom in to specific details—individual user interactions, data points, customer stories, edge cases. Here you ask: "What's the friction in this exact moment?" or "Why did this specific customer churn?"

The key is the movement between altitudes. Zoom out to gain perspective and identify strategic opportunities. Zoom in to find concrete evidence and specific problems to

solve. Then zoom out again to see how those particular insights might apply more broadly.

I've found this particularly valuable in product strategy work where you need both the big picture market opportunity and the granular user pain points to build something people actually want.

When Frameworks Break Down

It's important to note that frameworks are guides, not guardrails. Sometimes the most crucial insight comes from abandoning the framework entirely and sitting with uncertainty. Sometimes the answer to "why" five times is "we don't know yet," and that honest acknowledgment is more valuable than forcing a root cause.

Try this week: Pick one recurring frustration—at work or in life—and ask "why" five times. Write down each answer. You might be surprised where it leads. Or you might discover you don't know yet—and that's valuable too.

The Dangers Are Real

I'd be dishonest if I didn't acknowledge the risks. Asking big questions can derail the focus on execution. When your team is in implementation mode, suddenly questioning the fundamental strategy can be disruptive and demoralizing.

I learned this the hard way early in my career. Two weeks before a major product launch, I started questioning whether we were solving the right problem. My team looked at me like I'd lost my mind—and they were right. There's a time for big questions and a time for focused execution.

There's also the trap of analysis paralysis. I experienced this in strategy consulting early in my career, where you get so caught up in asking bigger and bigger questions that you never actually do anything. Sometimes you need to answer a question well enough and move forward, not perfectly. Perfect is the enemy of done, and done is the enemy of shipped.

The key is knowing when to ask big questions. During planning and strategy sessions? Absolutely. When exploring new market opportunities? Essential. During the quarterly review, when something isn't working? Critical. But when you're three weeks from a vital launch and the core strategy is sound? Hold your questions and focus on execution.

Big Questions in Practice

Let me share a few concrete examples of how asking big questions has led to breakthrough insights:

Inspire-Inc.org

When I was in my early twenties, on a Saturday morning, I sat around a kitchen table in Boston's South End, chatting with three friends about the best way to give back to the community. One friend talked about painting school classrooms. Another shared his experience mentoring a 10-year-old through the Boston Big Brother program.

Then one of my friends had a thought: all of these are things we could have done as 16-year-olds. But what is it that we, as strategy consultants, could do that we couldn't do earlier? What unique skills and access do we have now that could create greater impact?

That question sparked a brainstorming session that led to Inspire Inc., a nonprofit that provides pro bono strategy consulting to educational and social impact organizations. Instead of painting one classroom, we could help organizational leaders make better strategic decisions that would impact thousands of students. Over 20 years later, Inspire continues to provide guidance to approximately 70 nonprofit organizations annually, bringing together consultants from leading strategy consulting firms.

The big question—"What can we uniquely contribute?"—transformed how I thought about social impact entirely. More importantly, it showed me that asking big questions isn't just for cosmology or physics labs—it works around kitchen tables too. Sometimes the most profound insights come from the simplest moments of curiosity.

Heisenberg's Uncertainty Principle

In 1927, Werner Heisenberg asked a question that would fundamentally reshape our understanding of reality: "Can we know both a particle's position and momentum with perfect precision?"

The conventional wisdom said yes—in principle, with perfect instruments, we should be able to measure everything about a particle. But Heisenberg questioned this assumption at the deepest level. Through rigorous mathematical analysis, he discovered something profound: the very act of measuring one property (like position) inevitably disturbs the other property (like momentum). It's not a limitation of our instruments—it's a fundamental property of nature itself.

This wasn't just an abstract physics insight. The uncertainty principle challenged the deterministic worldview that had dominated science since Newton. It suggested that at the quantum level, nature is fundamentally probabilistic, not deterministic. By asking whether perfect knowledge was even possible, Heisenberg opened the door to quantum mechanics—arguably the most successful scientific theory in history.

I've found that asking "Can we actually know this?" is equally powerful in product work. It stops teams from spending months building elaborate solutions to fundamentally unknowable problems. Sometimes the most significant insight is realizing what you can't know—and building accordingly.

Philosophy's Deepest Questions

Philosophy tackles the biggest questions humans can ask. I've spent years wrestling with two in particular:

"Why is there something rather than nothing?" This question strikes at the heart of existence itself. The philosopher Gottfried Leibniz posed it in the 17th century, and we still don't have a satisfying answer. Science can explain how the universe evolved from the Big Bang, but it can't explain why there was a Big Bang in the first place—why existence exists at all.

I won't pretend that wrestling with this question yields practical applications. But it does something equally important: it trains your mind to question the most fundamental assumptions. If you can ask why existence itself exists, you can certainly question whether your product strategy makes sense or whether your business model serves the right customers. The habit of curiosity matters more than having all the answers.

"What is the nature of consciousness?" This might be the most profound mystery in all of science and philosophy. How does subjective experience—the feeling of what it's like to be you—arise from physical matter? Why do we have inner mental lives at all? Philosophers call this the "hard problem of consciousness."

Despite remarkable progress in neuroscience, we still don't have a good answer. We can map which brain regions activate during different experiences, but we can't explain why it feels the way it does to have those experiences.

This question matters beyond philosophy. As we build increasingly sophisticated AI systems, I assume they cannot be conscious—they process information without subjective experience. But this assumption forces a deeper question: What exactly distinguishes consciousness from sophisticated information processing? I don't know the answer, but asking the question shapes how I think about building AI responsibly. Sometimes the biggest questions don't get answered—they get lived with.

The Payoff

Here's what I've learned through decades of asking big questions: asking the biggest question you can think of in any situation creates a framework for everything else. Once you've explored the edges of a problem space, the smaller questions become clearer. The path forward reveals itself not in spite of asking big questions, but because of them.

That fourteen-year-old watching Cosmos didn't know he was developing a lifelong approach to thinking. He just wanted to understand the universe. But that curiosity—that willingness to ask "what's the biggest question here?"—has shaped every major decision I've made since.

From building products to writing about how I think, the throughline has been asking: What's the biggest, most fundamental question I can ask right now? What would unlock everything else?

Sometimes the answer leads to immediate action. Sometimes it leads to years of exploration. Sometimes it leads nowhere—and that's valuable information too.

Your Turn

So I'll leave you with this: What's the biggest question in your life right now? Not the most urgent or the most practical—the biggest. The one that, if you could answer it, would unlock everything else.

Maybe you keep having the same argument with your co-founder and need to ask, "What are we really disagreeing about?" Maybe your product has excellent features, but poor adoption, and you need to ask, "What job are customers actually hiring us for?" Maybe you're successful but unfulfilled and need to ask, "What does a life well-lived mean to me?"

You don't need to have the answer. Sometimes just asking the question is enough to start the journey. That's what happened for me at fourteen, and I'm still on that journey today.

What big questions are you wrestling with? I'd love to hear your thoughts.