(FORTUNE Magazine) – "Has Enron become a risky place to work?"

That was a pretty dumb thing to ask at Enron in August 2001. Risky? The firm was apparently flying high. Its stated goal, which could still be asserted with a straight face, was to become "the world's greatest company." But that dumb question was the very first line in Enron accountant Sherron Watkins's famous memo to Ken Lay. The answer was clearly yes, and the implication equally clear: Fix the mounting disaster ASAP. But no one in authority had the courage to follow where that seemingly dumb question led.

If anyone had, he would have discovered a powerful insight into business success, one that applies to every industry on every continent in every era: Dumb questions lead to smart decisions. We're not talking here about life's truly dumb questions. (Doesn't it count that I was thinking of you the whole time?) Rather we're talking about the dumb questions of organizational life, the ones no one will ask in a meeting because they sound heretical or disrespectful or just ... stupid.

The dumb question is none of those things. Instead, it can cut to the heart of the matter, posing a blunt challenge to someone or something--an authority, a policy, the established order. It can make people uncomfortable. Go there, and you're asking for trouble. When the organization strikes back, it doesn't condemn you as a threat but rolls its eyes and suggests you don't know the basic facts or are too dim to see what everyone else can see. Employees instinctively understand the danger. Remember, Sherron Watkins sent that memo anonymously.

As an example of how penetrating such questions can be, and why they're so difficult to ask, consider the most famous dumb question in all of business, created by Peter Drucker more than 50 years ago: What business are you in? If you ask that question as an ordinary employee at your company, the response would not likely be welcoming, and the odds would be long against your even getting to ask, let alone get answered, any of Drucker's famous follow-ups. (How's business? Who are your customers?)

Yet for decades companies paid Drucker impressive sums to visit them and ask those questions. So here's another insight into dumb questions: They're asked much more easily by outsiders. Consultants aren't the only outsiders who can get away with them. So can teachers. Socrates was the greatest asker of dumb questions in history. (What is virtue?) Children too--as noted in a previous article, a child's simple question led to the invention of the Polaroid camera.

And of course a free pass on dumb questions goes to one other class of people: bosses. It's a shame so few of them use it, especially when the stakes are high. Consider the experience of President Kennedy, who did not ask the obvious dumb question during the planning for the Bay of Pigs operation: What makes us think the Cuban people will rise up? Later, during the Cuban missile crisis, he had learned his lesson and no longer cared how ignorant he appeared. Tapes of his Oval Office briefings show him asking, How do you know this is a medium-range ballistic missile? How advanced is this? How long before they fire? Historians believe Kennedy's revised style of decision-making helped lead him toward the naval blockade and secret diplomacy that may well have averted nuclear war.

But you aren't worried about nuclear war, just the possible annihilation of your company or career. You're not a consultant or Socrates or a kid, and you're not the CEO. Can you risk asking dumb questions? Can you risk not asking them? Which will you regret more? You know the answer.

So here's how you do it. Don't apologize in advance or allow as how this is probably unimportant or say any of the other things that sap the dumb question of its power. Just step up and ask it. The shorter the better. Don't be intimidated by the stunned silence that follows. Wait it out. The payoff is on its way.

In that brief eternity, you'll understand more acutely than ever why dumb questions require courage. Just remind yourself that if they didn't, they wouldn't be worth asking.

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