In 2013, Target was certain Canada would love it.
Canadians already crossed the border to shop its US stores, so the brand assumed the welcome would simply follow them home.
It opened more than 120 stores in a single year, the largest expansion in the company's history.
Then the shelves sat half empty while the warehouses overflowed, and the prices ran higher than the ads had promised.
Within two years Target was gone, and around $2 billion with it.
Underneath it, Target was simply too sure.
It had already settled on the outcome it wanted, so the only question left was how fast to reach it.
The question it never really asked is the one most leaders skip.
How likely is this, really?
Annie Duke spent two decades at the poker table before she wrote about decision-making. Her case in Thinking in Bets is simple: every decision is a bet on an uncertain future, so the question that matters is how sure you are, and at what odds.
But asked to guess those odds, most of us reach for a hopeful number, because the mind that made the decision also defends it.
So flip the question. Instead of predicting success, assume the decision has already failed a year from now, and ask what went wrong.
The psychologist Gary Klein gave that move a name: the premortem. It rests on a 1989 finding that imagining an outcome as something that has already happened lifts your ability to identify its causes by about 30%.
Now you're not guessing at a number. You're looking at a list of named reasons you can do something about.
This is something I keep coming back to whenever I write about probability, because you judge an outcome far more honestly once you let yourself treat it as already real.
Target's leaders had everything they needed to see it coming. A premortem in 2012 would have put the failure on the table: shelves it couldn't keep stocked across that many new stores, and prices high enough to send shoppers back to Walmart.
None of it needed hindsight.
Your own decisions deserve the same hard look while they can still be changed.
Take the decision you're most confident about this week.
Move twelve months on, assume it has failed, and write down every reason you can, as though it already happened. Then ask the people who will deliver it to do the same alone, because the doubts no one voices in a planning room come out once failure is the premise.
Rank what comes back by how likely it is and how much it would cost. Fix the top of that list before you commit another pound or another week.
