The pre-mortem is more useful than the post-mortem
The post-mortem is a ritual we do after the project failed.
The pre-mortem is the same exercise, done before the project starts.
Imagine, vividly, that the project has failed. It's a year from now. You're standing in front of a room of teammates, customers, investors, friends. The project is dead. Why?
Write down every reason.
The pre-mortem catches things the optimism of the kickoff hides. People who were too willing to publicly disagree at kickoff become candid when the project is hypothetically already dead.
The questions get specific.
What killed it? Was it pricing? A wrong assumption about who the customer is? A founder relationship that broke? A regulatory issue we didn't model? A team member who quit at month four?
For each killer, you can ask: what would we do today, before we start, that would prevent or absorb that failure?
The pre-mortem turns into a checklist. The checklist turns into the plan. The plan is now stress-tested by hypothetical failure before any real money has been spent.
Three things to know about pre-mortems:
People are much more honest in a pre-mortem than in a kickoff. The pretend-failure framing gives them permission to voice doubts without seeming negative. Use that.
Most projects die for two or three reasons that are visible at the start if anyone bothers to look. The pre-mortem makes them look.
The cost of an hour of pre-mortem at kickoff is laughably small compared to the cost of finding out the same things in year two.
Run the pre-mortem before every project that matters.
It is the cheapest insurance policy in operating.