Forward Trajectory
Leadership and culture 4 min read

Back the daring mistake

The idea

Not all mistakes deserve the same response. Judge a mistake by the direction it was facing before you judge it by its cost.

Where it comes from

Winston Churchill, speaking in the House of Commons on 7 May 1941, as told in Andrew Roberts’ biography Churchill: Walking with Destiny (2018).

The story

In the spring of 1941 Britain had just been thrown out of Greece. At the same time a German force under Rommel had crossed the Libyan desert far faster than anyone in Cairo thought possible and pushed the British back to Tobruk. Parliament wanted an explanation, and Churchill chose to give it in the hardest possible way: he put down a motion of confidence in his own government and stood up to defend it.

He did not hide behind his generals. He told the House that the commanders on the spot had believed two things. First, that no superior German force could get across the desert that quickly. Second, that if one did, it would not be able to feed and fuel itself. The first belief, he said plainly, had been wrong.

Then he said something that has stayed with me since I highlighted it. Anyone who expects a war without mistakes is a fool, so the useful question is not whether a mistake was made but what kind. There is “a mistake towards the enemy”, the kind that comes from daring, from moving at the problem. Commanders who make that kind of mistake must always be backed. And then there is the mistake made on the safety-first principle, the kind that comes from turning away, from hanging back. Those, he said, deserve a far harsher look.

An MP had reminded him of Frederick the Great’s rule that it is pardonable to be defeated but not to be surprised. Churchill’s answer was that when your enemy is bigger and better equipped, and sits in the middle of the map with seven or eight directions to strike in, you cannot be ready everywhere for everything possible. You will be surprised. The only choice is whether your people are surprised while attacking or while sitting still.

The House backed him, 447 votes to 3.

What I like about this is that it is a rule for reviewing failure, not a slogan about courage. It tells you where to be generous and where to be hard. And it has a quiet second effect: once people know that the daring mistake will be defended, they make more daring moves.

A question to sit with

Think of the last mistake someone on your team made. Which way was it facing, and did your reaction match?

Created with the help of AI.

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