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Think Like a 5-Year Old (the Best Leaders Do)

Jeff Hoffman is the co-founder of ColorJar, is a serial entrepreneur who was on the founding teams of Priceline.com and uBid.com. He is also a frequent public speaker on the topics of innovation, entrepreneurship, and leadership.

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A few years ago, I was in charge of my five-year-old niece for the day. As is often the case with five-year-olds, I was about to get a whole lot more than I bargained for.

I needed to run to the office for a minute–I was then the CEO of Virtual Shopping Inc., an early e-commerce player later sold to Europe’s Wallenberg Group–so I told her to get in the car. As we walked to the garage, she looked down at the carpet and asked me how carpet is made. I knew there were big machines that sewed it, or something like that, but I didn’t know much more. She was clearly disappointed.

When we got to the car, she tapped on the window and asked me how to make glass. I explained that it involved fire and sand. She looked at me like I was crazy. I was losing, two-zip. To a kindergartner.

When we got to the office, my niece did what all kids her age do. She questioned everything. “What is that thing? Why do you have two of those? What does that guy do? Why is that girl on the phone all the time?”

Exasperated, I silenced her questions with a bag of Cheetos. But when I sat down at my desk, something bothered me. It wasn’t that she asked all those questions. It was that I didn’t know the answers.

I thought: Why do we have two of those? What is that thing on the counter? And what about that girl on the phone all day?

Here’s what I realized. I had gotten so used to my surroundings that I stopped seeing them. I got so used to the way I do business that I stopped questioning it. I had lost my child-like sense of wonder, that endless curiosity about the world around me. And it was a good bet that my employees had, too.

So here’s what I did. I told my employees that I wanted us all to find our child-like sense of wonder again, and to start to ask basic questions about the way we did business. They loved the idea, even before they saw the results. And you know what? It worked. For example, those two things my niece saw? They were collating machines that no one had used in years. The person who ordered them no longer worked for us. And even worse–they were on a monthly lease!

I took it a step further. I got the team to play the “wonder” game about everything at the company, all our daily tasks. As a result, we discovered there was some work we were doing that no one understood why. Not even our customers! By reigniting a child-like wonder and questioning everything, we started to totally streamline the business.

After that day with my niece, I decided to force myself to wonder–about something I would not normally wonder about–on a regular basis.

My first wondering session was on why I can call an airline three times in a row (this was before online travel sites existed) and get three different prices for the same flight. Like a good, inquisitive five-year-old, I just kept asking why, until I could find an answer.

In this case, there wasn’t an answer. So I started a company, Competitive Technologies, which made a robotic airfare search engine that grabbed up all the lowest fares for customers. Three years later, American Express acquired this company as part of a larger nine-figure deal. Good thing I reclaimed my child-like sense of wonder.

Do you still wonder about things the way you did when you were a child? Or do you walk past the same scenes every day, never pausing to notice what’s what. Make it a point to stop, wonder, and ask an endless stream of questions. They’ll lead you somewhere, I promise.

 

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