The audacious ask

On the delicate art of fearlessly asking “why”

Photo 1: 
Amy Cosper

A couple things here. First, change is hard. That’s been established. Second, fear is usually the reason change is hard. This is especially true for family businesses whose roots run deep with traditions. There is a grandness to harkening back to traditional ways of thinking and doing things. What we’re talking about here is why:  Why things are done the way they are, and what you, as leaders, can do about changing it. Start with asking the timeless, single-syllabled question: “Why?”

Chances are high that the first time you ask why something is done a certain way, the response will be, “That’s the way it’s always been done.” Not ideal, but it is an opportunity to change the way you approach things with critical thinking. And it limits your progress, slows down or squashes innovation altogether and, in the end, will cost you money and market position. New ways of doing things and new ideas always start with Why. Never accept the fact that things are done a certain way because that’s how things are done.

Children and scientists are good at asking big, beautiful, bottomless questions. Sometimes they ask too many of these questions at 4 a.m. when you’re in a beta sleep. “Why do the clouds stay up in the sky?” “Why do you talk to the dog?” Asking why is the basis for the scientific method (for scientists, not parents).

Why is it so hard to ask this question? Sometimes your boards fear change the most. Sometimes leaders fear change. Employees definitely fear change. It’s stepping into the unknown  –  taking a leap of faith. But that fear will paralyze you and your organization every time, which makes change and innovation challenging.

It is an audacious ask that requires a modicum of fearlessness. If humans never asked why something is done a certain way, we wouldn’t have the breathtaking acceleration of technology, AI, rovers on Mars that we are witnessing in our lifetimes. Think about it. “Why?” you ask. Why not? Anything is possible if you challenge the known ways of doing things –  especially in family business. Traditions can be changed for the better.

If you don’t ask why something is the way it is, you’ll never know the answer. That means you’ll miss opportunities - and the opportunity to innovate.


Amy C. Cosper

Twitter me @AmyCCosper

How do you approach change and fear? Let me know. What’s your story, anyway? We’d love

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