Curiosity as an Advantage

“You see things; and you say ‘Why?’ But I dream things that never were; and I say ‘Why not?’”

George Bernard Shaw, Back to Methuselah (1921)

I grew up with that line taped to our refrigerator. My father cut it out of the newspaper when I was young, the version President Kennedy used in a 1963 speech. Kennedy’s wording differed slightly from Shaw’s, but the intent was the same: curiosity is necessary and good.

For years I didn’t understand why it mattered, or how it would shape the way I see the world. Now, several careers later and a long way from the eight-year-old who read it every morning, I have a better appreciation for what Shaw and Kennedy were pointing at. We can choose curiosity as a course of action, both to understand what is and to imagine what could be. When we do, we open more possibility than we thought.

So why does curiosity matter so much in business? Curiosity works two ways. First, it asks what is, to understand the world as it works. Second, it asks what could be, to see what opens when a constraint is removed. In the first instance, a leader can aim curiosity in three directions: inward, at their own internal narrative; outward, toward their people; and within the organization itself, the systems and processes that drive it. In the second instance, a leader can utilize curiosity as a tool to shape ideas and perspectives by offering a glimpse of a future that doesn’t currently exist. Leveraging both, across all three directions, is what lets a leader navigate complexity and risk.

Curiosity to Understand “What Is”

Let’s start with asking about “What is”.

First, the inward look. It’s easy for leaders to make assumptions about how people are, or how their world works. I’m not saying those assumptions are always wrong. But, they rest on your internal narrative, and selective data skews the assumptions you make. How many times have you read an email from an employee or a peer and thought, “I can’t believe this,” as your frustration rises? In that moment, your internal narrative is telling you a story, one built from the data your mind selected for you. Your bias shapes the facts into something easy to accept, steering you away from the information that says “You might be wrong.” because being wrong feels like a threat.

When we get curious about what your internal narrative is suggesting, we start to ask questions that allow us to see the situation through the other person’s eyes. We begin to understand the situation as it is unfolding as reality, not just through our idea of what reality is; allowing us to connect with the team more genuinely and see the world as it is. It matters little whether we agree, or disagree, with the other person’s perspective. What matters is acknowledging that perspective and using it to gain clarity around a situation or the person themselves.

Turned outward, curiosity helps a leader learn what is happening with their people. What is the state of the team right now? Is the workload sustainable? Is something at home following someone into work? Asking these questions is a way to connect, and it keeps assumptions from substituting for facts. A salesperson who was killing it last quarter, but is now struggling to keep up? It’s easy to assume they’ve stopped caring or run out of leads. That might be true. It’s also possible something at home is pulling their attention away from work. It’s through curiosity that a leader could learn that issues at home are intruding at work, allowing them to take a few things off the salesperson’s plate, giving them space to handle it. A few honest questions build trust, show the person you see them, and often bring back a stronger teammate who doubles down.

Turned toward the organization itself, curiosity lets us see past your own view of the picture, whether tactical, operational, or strategic. It’s tempting to believe the way we see things is genuinely reality. Isn’t it the leader’s job to be the expert on everything, and understand everything? Good news… it isn’t. Our view is shaped by our background, our training, and our assumptions. Asking what is really happening in the organization, or with the customers, is like turning over rocks. We don’t know really what we’ll find. Now and then it’s gold. More often, it’s worms and bugs. And that’s good, because now we know where the problems are and how to go after them. Applied to the organization, curiosity could enable a shift in the way it does business creating greater efficiency and effectiveness, reducing costs and increases profit. Put the experience of the people doing the work every day toward solving those problems, and both customer and employee satisfaction improve. If we never (or rarely) talk to the customer, or to the people who do, we can’t assume we know what they want. Ask the people who talk to them daily. Better yet, spend a day in the work.

Curiosity to Understand What Could Be

When we were eight, imagining a different world cost us nothing. We haven’t been taught yet how things supposedly have to work, so our imagination runs free: exotic animals to find, new worlds to conquer, new ways to explore the one we’re in. Somewhere in adolescence that stops… the world is what it is, and that is that.

As adults, dreaming of things that never were and asking “why not” gets much harder. We treat the constraints in front of us as fixed and assume we must operate inside them. If that were true, if every constraint were as solid as it looks, we would never have put humans on the moon or a computer in everyone’s pocket. Those things happened because someone refused to accept a constraint as final. They pictured something that did not exist, then asked, “Why not?”

“Why not” takes a constraint and asks us to prove that it’s real. Some constraints are real, and in understanding that we can plan around them. But when we find the constraint doesn’t really exist, that’s when new ideas can flourish; that’s when we can drive towards building something truly unique, or again, drive efficiency for the team.

This is where the two sides of curiosity meet. “Why” shows you the world as it is, including which walls we believe can’t be moved. “Why not” tests the walls, to see if they are, in fact, immobile. Lead with “why” alone and we might understand everything… yet build nothing new. Lead with “why not” alone and we’ll chase ideas without knowing which limits were ever real. Held together, they let a leader see what is, reach for what could be, and create better outcomes.

Why it’s hard

It sounds simple. Just be curious. So does winning the lottery. But it’s never that simple. There are barriers I have experienced in the past and continue to see in others that I work with.

First, many leaders earned the job because they were the best at the work itself: the standout individual contributor, the engineer who became the manager, the founder who built the first version alone. That expertise made them the person with the answers, and after a promotion they hold onto that identity. “I’m here because I’m good, so I should be able to solve this.” They lean on their own knowledge, discount what a more junior voice might offer, and forget to ask what else might be true.

Second, we all carry bias, and it’s hard to see our own. That blind spot keeps us from asking the questions that would challenge it. We see the world the way we expect to, and our internal narrative confirms it for us. Then we project it outward, assuming other people think and feel the way we do, or the way we’ve decided they do, without ever checking.

Third, people hate being wrong. Leaders often hate it more… much more. The fear is that the team will see them as less of a leader, as out of their depth, or as weak for asking too many “silly” questions.

All three barriers share a root: ego. We let ego stand between us and our own curiosity. It shields us from the discomfort of not knowing, of being wrong, of seeing our bias, of learning we misread someone. It is very good at that. What it cannot shield us from is failure. Failure to find the best solution. Failure to build a stronger team. Failure to read a complex situation in time.

How to Practice Curiosity

So how do you get better at leading with curiosity? Here are five steps I use to maintain my curiosity.

1. Tell your ego to take a seat. Give yourself permission not to have every answer, and to be wrong. Ask what would really happen if you were wrong.

2. Ask “what” and “why.” Sakichi Toyoda, the founder of Toyota Industries, built a method around this called the Five Whys: keep asking why, often five times or more, until you reach the root of a problem rather than its symptoms. Taiichi Ohno later made it central to the Toyota Production System. Use “why” questions to dig into a problem or a system. Use “what” questions with people, since they invite more honest answers without putting anyone on the defensive.

3. Seek out perspectives different from your own. Fresh viewpoints unlock creative ways through hard problems. Most business problems have shown up before, somewhere, in some form. A different vantage point often surfaces a solution that worked elsewhere and can be adapted to fit.

4. Go see for yourself. Step into the work your team does every day. Nothing replaces the understanding you get from standing where the work happens. I once spoke with an airline CEO who learned about a persistent radio problem between his aircraft and the gate only because he took a flight and sat in the cockpit as they taxied in. The issue had been raised over a year before that, but it never got to his level. Working beside his people let him see it firsthand and fix it within days.

5. Ask, “If there were no constraints, what could we do?” Try to see the situation through the eyes of an eight-year-old. What could we build? How could we connect with the people we serve? How would we operate if the usual limits were off the table? This doesn’t mean the barriers are easy to clear. It means that picturing what’s possible gives a leader something real to move toward, and others to bring along.

The environments most leaders operate in have shifted from complicated to complex. Complicated problems have a right answer you can work out. Complex ones have several workable answers, many wrong ones, and trade-offs that pull against each other. Finding a good path requires asking real questions and listening to others for the answers. Curiosity in “Why” and “Why not”, across all three directions, is what gives you enough of the picture to see risk before it’s upon you or the organization, and to choose well when the answer is not obvious.

Good solutions rarely come from one person, or one way of thinking. The leaders who treat curiosity as a discipline, a way of operating every day, are the ones who get the most out of the people around them and most often generate the best solution to the problem.

About the Author

Jason Simon is the founder of Uncaptured Leadership, an executive coaching and leadership development consulting practice. He helps executives and general managers hold competing leadership demands under pressure without losing their edge, while creating high-performance teams. His leadership background includes 20-years as a Naval Aviator flying the F/A-18 Super Hornet, CEO of a B2B SaaS company, and leading across functions in high-risk, high-consequence environments. He holds an MBA from the University of North Carolina and is a Georgetown University credentialed, International Coaching Federation certified coach (ACC). Reach him at jason@uncapturedleadership.com or uncapturedleadership.com.