They say a good lawyer never asks a question for which he doesn’t already know the answer. The lawyer doesn’t want to be surprised and wants to achieve a particular result with the questioning. But that’s the opposite of what real questioning should do.
Experimentation, creativity, and play are all natural, fundamental human traits that often lead to surprising results and, in some cases, have the potential to move humanity forward. That’s why I love “What if” questions.

Think of a meeting where people are trying to solve a vexing problem. Then somebody suddenly says, “What if…” It usually starts some off-the-wall idea, followed by dismissive arguments to the contrary, then a few “Well, maybe…” responses, and finally something like, “You know, that’s so crazy, it might just work.”

When we were kids, play was often about experimenting. If I dig a hole in the dirt, how deep could I go? What will I dig up? What if I used something other than a shovel? What if I used a garden hose? 

And we learned about dirt, mud, digging, bugs, worms, roots, rocks, the power of water, how tools work, and some basic engineering. But we didn’t know we were learning. We were just having fun. That’s why it was called play.

As adults, our “What if” questions tend to be directed. We want to explore new ways of manufacturing or new ways of marketing. Rather than a surprise, we’re searching for a particular outcome, just like that lawyer who already knows the answer. That’s not likely to gain anything approaching a paradigm shift.

When I give pricing workshops for custom woodworking businesses, I emphasize that one of the reasons they need to add enough profit in their pricing is to fund research and development, but I suspect most don’t seriously have anything like an R&D program. Planning for the future is not a custom woodworking strong suit. We don’t have time for play and experimenting.

My first experiences in business and manufacturing were made in the heady early days of Silicon Valley. I was not directly involved with the blossoming tech world there, but I was surrounded by it. Everything was about new ideas and experimenting. I had a friend who was curious about computer-aided drawing, so he took some AutoCAD classes. Soon he was in demand as a draftsman, job-jumping every six months and doubling his salary at each change.

I personally met people in lots of different fields who kept asking “What if” questions that propelled them into new enterprises. There was little worry or talk of failure because they were all too busy following the path of the questions. A couple of those questions led me into my first two businesses and paid for my college degree.

Even today, I can’t help asking “What if…” over and over again and seeing what will come of it. Maybe we all need to take more time for a little play, a little questioning, a little curiosity. Who knows where it will take us?