Prevent your next failure.
Most leaders plan forward and get blindsided. This workout runs time backward — twice. First you imagine you failed and ask what killed you. Then you imagine you won and ask what you did right. Both change what you do today.
What this protects
You, from avoidable failure — and the version of you that gets blindsided because optimism buried the risk. Run it often and you stop being surprised by the things you could have seen coming.
Why this works
When you ask a team "what could go wrong?" they hedge — nobody wants to be the pessimist. But when you say "it's a year from now and this failed — what happened?", the doubts pour out. Certainty gives permission that speculation doesn't. That's the psychologist Gary Klein's pre-mortem, and it surfaces the risks optimism buries.
Hindsight is 20/20. A pre-mortem borrows it — before you need it.
Backcasting flips the lens. Instead of forecasting forward from today's constraints, you stand in the finished success and look back at the path. It frees you from "what's realistic now" and reveals the moves that actually got you there. One tool shows you the cliffs; the other shows you the trail.
Lens 1 · Pre-mortem
"It failed. What killed it?"
It's a year out. The thing you care about most has collapsed. Write the obituary — the real reasons, the ones you can already half-see. Each one is a risk you can defuse now.
Lens 2 · Backcasting
"It worked. What did I do right?"
Same year out. It succeeded beyond expectation. Look back and trace the path — the decisions, habits and bets that got you there. Each one is a move you can start now.
Reflect · pick something that matters and run both
Pre-mortem: a year from now this failed. Name the three most believable reasons why.
Backcast: a year from now it succeeded beyond what you hoped. What are the three things you did that made the difference?
Of those six, which one — a risk to defuse or a move to start — would you act on this week?
Take your one move — and make it real before the week is out.
Defuse the risk or take the first step of the path. Then, if you lead a team, run the pre-mortem with them on your next big bet — "it's failed, what happened?" — and watch what surfaces.