As leaders we dread the word. You make a decision, you issue an order, you write a policy, and then someone inevitably approaches you with that one-word question. It makes you grit your teeth and hold your breath. You count to ten before you answer. Sometimes the decision, order, or policy was not even yours, but it comes down from above and you have to defend and implement it. And it is never just one person that has this question, but dozens, perhaps hundreds. Well get used to it, because if you call yourself a leader you are going to have to deal with it for the rest of your life. The question, of course, is “Why?”

I have been looking at my fourteen-month-old daughter waiting and wondering when that heinous word is going to start spewing from her lips, torturing my very soul into her teenage years and beyond. I am sure my parents have a good laugh now and then, thinking that I am getting my comeuppance. Make no mistake, being a parent is a leadership position, so take heed and beware the temptation to always use the old, “Because I said so!” response. It probably doesn’t fly at work, so refrain from using it with nimble, young minds, which are seeking knowledge and guidance.

I am early “Generation X” so my role models during my formative military and police career were old school baby boomers who did not believe in questioning orders or directives. They said, I did. It seemed pretty clear-cut and simple to me, because I trusted them. I guess I expected that once I occupied leadership positions that I wouldn’t get questioned either. Someone forgot to tell me that most Gen-X-ers, and this new, aptly named “Generation Y,” is all about questioning authority.

I am an avid reader of military history. It is rare to find narratives of great military campaigns where the premier generals were constantly questioned. As I was considering this month’s column earlier this week, I came upon the famous portrait of Washington crossing the Delaware. It gave me a chuckle to wonder if Private Snuffy rowing behind the General would have ever thought to ask him, “Why are we up so early this cold morning, rowing across this half frozen river?”

So how do we leaders deal with this phenomenon? First, it is important to realize that all leaders are dealing with this question, so don’t get frustrated or upset. You are not alone. Most of the time your authority, intention, integrity, and judgment are not being questioned. More often than not, the reasoning behind the order given is what is being questioned.

Try to look at the question “Why?” as an opportunity to train, inform, teach, and mentor the person or group who is asking. I like to think that General Washington, in a firm, fatherly voice, would have told the young man who asked him the dreaded question, “Son, we need to win a battle in this War of Independence and this is the best way I know how to get the jump on those bad, old Hessians over there!”

Let me make one disclaimer here. When training your people, make it abundantly clear that there is a time for questioning and a time when following orders could mean the difference between life and death. In an administrative situation, or in a debriefing situation, questions are an opportunity for the leaders to improve their organization. In a tactical situation, however, there is little room for discussion beyond clarification of directions. Don’t forget it!

Lastly, consider the quote by George Bernard Shaw one more time. Look behind it. As leaders we have a choice to make. Do we also question our leaders with “Why?” Or do we decide to focus on the possibilities of what can be built, of what can be accomplished, or of what dreams can be made reality? Ask, “Why not?”