The decisions you can afford to get wrong

Watch where a week actually goes and a pattern shows up. A small number of genuinely consequential decisions get made quickly, often in a corridor. Meanwhile a large number of trivial ones absorb enormous amounts of deliberation, because they arrive with a feeling of importance attached that has nothing to do with their actual cost.

The sorting question is simple and almost nobody asks it: if this turns out to be wrong, what does it cost to undo?

Two questions, four kinds of decision

Ask what it costs to reverse, and how long you will wait for information that would materially change the answer. That produces four cases.

1. Cheap to reverse, information available soon. Decide now, badly if necessary. Waiting costs more than being wrong. Most tooling choices, most scheduling, most first drafts.
2. Cheap to reverse, information will not arrive. Decide now. There is nothing to wait for and the reversal is affordable. This is where the largest amount of time gets wasted.
3. Expensive to reverse, information available soon. Wait, but set the date you will decide regardless, and name the specific thing you are waiting for. Otherwise this becomes case four by neglect.
4. Expensive to reverse, information will not arrive. The genuinely hard ones. Slow down, seek counsel, write the reasoning down so that you can tell later whether it was a bad decision or bad luck.

Case four is rare. Most people face a handful in a working life: a career change, a house, a business partner, having children. Everything else is one of the first three, and the first three should be fast.

The tell for a decision being deferred wrongly

When a decision keeps appearing on an agenda and keeps being deferred for more information, ask what specific piece of information is being waited for and what will change once it arrives. If nobody can name it, the decision is not waiting on information. It is waiting on somebody being willing to own it.

That is a different problem and no amount of further analysis touches it. It is also extremely common in teams, and it is one of the more useful things a half day workshop resolves, usually within the first ninety minutes and often by discovering that two people in the room believed the decision had already been made.

Write down the reasoning, not just the choice

For anything in case three or four, write a short paragraph at the time: what you chose, what you expected to happen, and what would tell you it was wrong. Half a page.

Its value is entirely retrospective. Without it, hindsight rewrites your reasoning to match the outcome, and you learn nothing from either a success or a failure. With it, you can distinguish a bad decision from an unlucky one, which is the only way judgement actually improves.

The cost of getting this wrong in the other direction

None of this argues for recklessness. It argues that deliberation is a limited resource and most people spend nearly all of it on the wrong category.

Someone who agonises for three weeks over a reversible choice and then makes a genuinely expensive one over a weekend has not been careful. They have been careful about the wrong thing, and the pattern is invisible from the inside, which is why it comes up so often in a session. Weeks five and six of the group program are built around this, and a reliable number of participants finish their eight weeks early because a decision they had been carrying for a year turned out to be case two.