In business, this 3-letter word can feel worse than most 4-letter words.

I was in the car with one of my three children.

Daddy, can we get donuts?

No, not today.


Because, we don’t have time.


Because, we’re running late.


We were being pokey this morning.


Because, we were up late last night.

If you are a parent, you are well acquainted with the endless barrage of whys. Everything is subject to questioning.

Somewhere along the way, we shake off the shackles of that 3-letter word. We stop questioning. In the hierarchies of life, we grow to accept words from the top as infallible and God-breathed.

Yet, I find myself endlessly challenged at home by the whys. Why shouldn’t we eat ice cream everyday? Why can’t we buy a hover board? Why can’t I have a new puppy? Why is your tummy so big?

Oftentimes as managers we don’t like questions. After all, it shines a light on the curse of knowledge—our assumption that because we know something, others must already know it too.

Or, perhaps we despise this simple question because we don’t know. We are doing something not because there is good reason or data, but rather for the simple, unquantifiable reason, because.

In the board room, it can be uncomfortable to ask why. You might not look like a team player. You might seem disrespectful, or worse, insubordinate.

But, asking questions is important.

I’m reminded of the funny story:

A woman in Arkansas brought her baby in to see the doctor. The doctor determined right away that the baby had an earache. He wrote a prescription for eardrops along with the directions: “Put two drops in right ear every four hours,” abbreviating “right” with an R. Several days passed, and the woman returned with her baby, complaining that the baby still had an earache, and his bottom was getting really oily with all those drops that the doctor prescribed. The doctor looked at the bottle of eardrops and sure enough, the pharmacist had typed: “Put two drops in R ear every four hours.”

Ridiculous? Perhaps.

But, it illustrates an important idea. We should look for the truth in the questions brought to us by those on our team. In those truths, we may find tremendous opportunities. And, we might find that those questions aren’t nearly as scary as they seemed.

The pain in the ask is—how comfortable are you with allowing others to ask why?

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