Sense and decide
Premeditatio malorum
Rehearse what could go wrong
Rehearse how a commitment could fail, in advance and time-boxed, so trouble arrives expected rather than as a shock.
Borrowed from Stoic philosophy, especially Seneca, who recommended rehearsing misfortune in advance. Psychologist Gary Klein's "premortem" is a modern version. Read the original source.
One session · Minutes to start · Anyone on the team can start it
Try this first
Ask the team to imagine it has already gone wrong, and say what happened.
Use it when
About to make a big AI-assisted commitment with optimism unchecked.
Skip it when
Save it for commitments where failure would matter. With an anxious team, endless catastrophizing does harm, so time-box it and turn it toward action.
How to introduce it
Before a significant AI-assisted commitment, spend a few minutes on how it could go badly. The Stoics practiced picturing setbacks in advance so the blow landed softer. Keep it bounded and pointed at real failure modes, not open-ended worry.
How to show up
Run a focused few minutes on how this goes wrong, and keep it on risks you can act on. Then make sure the risks named get planned for.
How long it takes
Five to fifteen minutes before a significant commitment.
What makes it hard
People resist imagining failure at the moment they commit, out of optimism or superstition. Calling it preparation helps. And it only pays if the risks get addressed, otherwise it is worry aired and forgotten.
What it looks like when it's working
The team names failure modes in advance and plans for them, so trouble arrives already anticipated. A list nobody acts on, or a spiral into anxiety, means it is being used badly.
How long until it sticks
Expect a few uses before imagining-failure-in-advance becomes a natural pre-commitment step.
How you know it stuck
The team asks how this could go wrong before a big commitment, and plans for the answer.
The idea behind it
Imagining failure is preparation, not pessimism. A team that has pictured the failure meets it ready.
Where it comes from
Stoic philosophy. The ancient pre-mortem, before a big AI-assisted commitment, spend a few minutes on "how could this go badly?" so the team meets trouble prepared, not ambushed. (Stoic negative visualization). Deliberately rehearse what could go wrong in advance so that, as Seneca put it, the blow is gentle when it comes. It's bounded and purposeful, not rumination.
Also fits: Risky or hard-to-undo steps go ahead without a stop