Attack your plan before reality does.
Plans look perfect to the people who wrote them. Red-teaming gives someone permission, and a method, to break them early.
Pre-mortem
Imagine It Failed
“It's six months on and this failed. Why?”
- Gary Klein's technique
- Everyone writes reasons alone first
Devil's advocate
A Rotating Role
“Let me argue the other side.”
- Assign it, so it isn't personal
- Rotate it every meeting
Red team
A Separate Group
“Our job is to break this.”
- Outsiders see blind spots
- Save it for high-stakes plans
Source: Harvard Business Review ↗
Find the holes while they're cheap.