Combine the pre-mortem with red team pressure
Run a pre-mortem and then ask the red team to find the failure mode the team missed.
Why it works
A standard pre-mortem asks team members to imagine failure and work backward. This activates concerns but is constrained by what each person is willing to voice in the group. A red team pre-mortem adds a second layer: after the group pre-mortem, the designated red team pushes specifically on the failure modes the group was reluctant to name or dismissed too quickly. The combination surfaces both the socially acceptable and socially risky concerns.
How to do it
- Run a standard pre-mortem: "assume the project failed — what happened?"
- After the group session, give the red team the list and ask: "what did the group not say that you think is actually the most likely failure?"
- Red team presents their additions without the social pressure of the main group.
- Integrate both outputs before finalizing the risk register.
Evidence
Pre-mortem research shows it increases identification of failure causes by reducing optimism bias. Adding a red team phase that surfaces what the group suppressed is a practitioner extension of the Mitchell et al. finding, not a separately studied combination. (mechanistic)
The pre-mortem effect is established; the combined pre-mortem + red team protocol is not independently tested. The logic is sound but the added value of the red team pass over a well-run pre-mortem is not established.
Sources
- Mitchell, Russo & Pennington (1989), prospective hindsight and predicting failure, Organizational Behavior and Human Decision Processes
Common mistake
Using the pre-mortem as a substitute for the red team rather than as a complement. The pre-mortem is self-critical; the red team is externally adversarial — they’re looking for different things.
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More practices for Red Teaming: Stress-Testing Plans Before They Fail
- Appoint an explicit devil’s advocate role
Give one person the formal job of arguing against the plan — making dissent structural, not personal.
- Map and stress-test your key assumptions
Before executing, list the assumptions the plan depends on — then ask which ones would kill it if wrong.
- Use reverse brainstorming to find failure modes
Ask "how would we make this fail?" instead of "how do we make this succeed?"
- Simulate the adversary’s response to your move
Assign someone to genuinely think and plan as your competitor, not just describe them.
- Require the plan to change, not just the risk register
A red team exercise that doesn’t change the plan has accomplished nothing.
Related concepts
- Decision Journaling: Learning to Decide Better Over Time
How to build a personal feedback loop for the decisions that actually matter
- Survivorship Bias: Learning from What You Can’t See
The invisible graveyard of failures — and how to reason from the full distribution
- The Eisenhower Matrix for Teams
Adapting the urgent/important split for shared priorities, delegation, and team alignment