Prompt · Strategic decisions
Pre-Mortem on a Strategic Decision
Imagine the decision has already failed; work backwards to what a foresightful board would have done.
When to use it
Before a material strategic commitment — an acquisition, a market
entry, a capital deployment, a restructuring. Pre-mortem analysis
(developed by Gary Klein) works because it changes the question from
“could this fail?” (which the board will answer “we have considered
that”) to “it has failed — why?” (which forces the specific failure
modes to be named).
The prompt
You are serving as a senior board advisor conducting a pre-mortem on a strategic decision that has been proposed but not yet taken.
The decision under consideration is:
[DESCRIBE THE DECISION IN NEUTRAL, REDACTED TERMS. INCLUDE: what is being decided, on what timeline, at what scale, against what strategic alternative, under what assumptions.]
Imagine the board approved this decision. Eighteen months have passed. The decision has turned out badly — meaningfully and visibly. The board is now reviewing what went wrong.
Do the following:
1. Write three distinct failure narratives — short, concrete, specific. Each should describe (a) what happened, (b) why, and (c) when the outcome became irreversible. The three should differ in kind, not just degree: market/external, execution/internal, governance/decision-quality.
2. For each narrative, identify what signals were visible at the moment of decision that the board did not sufficiently weight.
3. For each narrative, identify a specific decision the board could have made differently at the moment of approval that would have avoided or meaningfully mitigated the outcome.
4. Write one paragraph the board chair might realistically write in an internal memo 18 months later, acknowledging the decision and what the board has learned.
5. Finally: identify the single most useful thing the board should do before approving the decision, given the three narratives above.
Be specific and concrete. Do not hedge with “it depends.” Avoid generic governance language.
What to supply
Redact as in the stress-test prompt. Describe the decision at the level
of structure and magnitude, not names and exact numbers. The pre-mortem
gets sharper, not weaker, when forced to reason from structural
features rather than specific identities.
What to expect
Three plausible failure paths that the current board discussion is
unlikely to have fully canvassed. The exercise is most useful in the
narrative form — pre-mortem reasoning becomes diluted when presented
as bullet-point risks rather than as plausible retrospective accounts.
The “internal memo” output is also unusually productive: it forces a
realistic register of accountability.
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