In chapter four of his book Blink, Malcolm Gladwell describes how Paul Van Riper, a retired Marine commander, drove the U.S. military to fits in a war exercise called “Millennium Challenge.” It’s a brilliant argument for the plan-as-you-go idea compared with the traditional plan method.

The Millennium Challenge was an exercise designed to test the military’s ability to deal with a simulated war in the Middle East. It pitted a very large team (Blue Team) equipped with a very detailed battle plan, a lot of computer models and simulations, against a very small team (Red Team) led by Van Riper, experienced and self confident and good at making quick decisions.

“Blue Team had their databases and matrixes and methodologies for systematically understanding the intentions of the enemy. Red Team was commanded by a man who looked at a long-haired, unkempt, seat-of-the-pants commodities trader yelling and pushing and making a thousand instant decisions an hour and saw in him a soul mate.”

As you’ve already guessed, Blue Team is the might of the military, and Red Team is essentially one smart guy who starts with a plan and revises it constantly as the battle ensues.

When the game was actually played, Van Riper surprised the Blue Team quickly with a move not in its plans, and as they reacted to that, he surprised them again, and quickly caused considerable unexpected damage to a much larger force. It was all simulated and hypothetical, but the result was that the quick-to-react team with flexible planning beat the pants off the very detailed plan team that couldn’t react to changes.

“Had Millennium Challenge been a real war instead of just an exercise, 20,000 American servicemen and women would have been killed before their own army had even fired a shot.”

That was pretty hard for the military to explain. They analyzed it a lot.

“There were numerous explanations from the analysts at JFCOM (Joint Forces Command Center) about exactly what happened that day in July. Some would say that it was an artifact of the particular way war games are run. Others would say that in real life, the ships would never have been as vulnerable as they were in the game. But none of the explanations change the fact that Blue Team suffered a catastrophic failure. The rogue commander did what rogue commanders do. He fought back, yet somehow this fact caught Blue Team by surprise.”

Implicitly, the problem was the big team full of computers and data trusted a static plan, while the other team didn’t.

Red Team’s powers of rapid cognition were intact—and Blue Team’s were not.

So relate that to the planning we want: planning that responds to rapidly changing reality. Not just “Duh, I can’t plan, I don’t know the future,” and not just “Why plan? Why bother” and not “We have to follow the plan,” but planning as you go.

Tim BerryTim Berry

Tim Berry is the founder and chairman of Palo Alto Software and Follow him on Twitter @Timberry.