THE GUT CHECK SERIES · Failure · No. 2
One leadership question, examined. A new one every Tuesday.

Do you (and they) know ‘WHY’?

A unit can execute a flawless plan in the wrong direction. I have watched it happen, and the after-action is always the same: everyone did their job, and the job was wrong. Not because they were careless. Because nobody made sure they knew why they were doing it.

We tend to treat the “why” as a courtesy, something you add if there’s time once the orders are out. It is the opposite. The why is not the preamble to the work. The why is the work, because it is the only thing that lets a person make the right call when the plan meets reality and the plan loses.

Here is the test underneath the question. Give someone the what and you have a body that follows instructions until the instructions run out. Give them the why and you have a mind that keeps serving your intent after the instructions are gone. The first survives contact with nothing. The second is the whole reason you trained them.

That is why the question asks about both of you: do you (and they) know why. Two failures hide in there, and they look identical from the outside. Sometimes the leader never knew the why and was just passing pressure downhill. Sometimes the leader knew it cold and never said it out loud, assuming it was obvious. The team can’t tell the difference, and it doesn’t matter to them. Either way they are executing blind, and the gap shows up at the worst possible moment, when something breaks and there is no time left to ask.

Providing the why is the cleanest example of the most useful thing a leader does: give people the context to act with judgment instead of waiting for permission. Context is not softness. It is the highest-leverage thing you own. A team that knows why can absorb a changed plan, a lost comm, a missing leader, and still move toward the thing you actually wanted. A team that only knows what stops the moment the what no longer fits.

In practice it costs you about two sentences and a little bit of ego. Before the task goes out: here is what we’re doing, and here is what it’s in service of. When something changes: the plan moved, the purpose didn’t. And the discipline runs upward too. If you can’t say the why in a sentence, you may not have one yet, and that is worth finding out before thirty people execute on your behalf.

The leaders I trusted most were not the ones with the most detailed orders. They were the ones who made sure I understood the point, and then got out of my way. They knew that a plan should not fail for want of a sentence, and a good person’s judgment should not go to waste for lack of context.

Gut check: the last thing you handed your team: do they know what it’s for? Or just what it is?

Row Well and Live.

Next in the series: Failure Is Tuition. The Gut Check series runs every Tuesday. See every question so far, or start at the beginning with Nobody Meets a Standard They Can’t See.