Historical Failure Analysis
Post-mortems reveal the same failure modes repeating across organisations, industries, and eras. Execution failure at handoff. Stakeholder misalignment discovered too late. Scope expansion under pressure that destroys the original design. Underestimated dependencies that required other things to change first. The failure modes aren't a mystery — they just don't get applied prospectively. This skill does that: surfaces which patterns are present now, before they become post-mortem findings.
Your Process
Step 1: Describe the Type of Endeavour What kind of thing is this? A product launch, an organisational transformation, a technology implementation, a partnership negotiation, a strategic pivot, a scaling operation. Describe it in type terms — this determines which failure mode library to draw from.
Framing check: Confirm the specific endeavour before continuing. State what you've identified — the type of endeavour and its key parameters (scale, stage, domain) — in one sentence, then use AskUserQuestion:
- Question: "I'm reading this as: [your one-sentence framing of the endeavour type and context]. Is that right?"
- Header: "Framing"
- Options:
- Yes — proceed — framing is correct
- Adjust — one element is off; user will correct it before you continue
- Reframe — different situation than read; incorporate the correction before proceeding
Step 2: Identify Common Failure Modes for This Type What do post-mortems and retrospectives reveal about this category? Draw from known patterns:
- Underestimated dependencies — other things had to change first (systems, processes, people, culture) that weren't included in the plan
- Stakeholder misalignment discovered late — different parties had different success criteria never surfaced and reconciled before execution
- Scope expansion under pressure — original constraints abandoned to satisfy requests; produces a thing that does everything adequately and nothing well
- Execution failure at handoff — clear plan, unclear ownership across transition points where accountability transfers
- Context assumption failure — the plan was designed for conditions that changed before or during execution
- Resource attrition — key people, budget, or attention lost before the initiative reached self-sustaining momentum
- Feedback loop absence — no early signal mechanism to detect problems while correction was still possible
Step 3: Test Each Against the Current Situation For each failure mode: is it present in current conditions? What are the specific early warning signs that would indicate it is activating? Be concrete — not "stakeholder misalignment might occur" but the specific evidence of it that is or isn't visible right now.
Step 4: Rank by Probability Times Impact
Before narrowing: Show the complete set of failure modes identified in Step 3 to the user first. Use AskUserQuestion:
- Question: "I've identified [N] failure modes present in current conditions. Before I select the highest priority, are there any you'd flag as especially critical, or any I've missed?"
- Header: "Prioritise"
- Options:
- Proceed with your selection — the set looks right
- Flag one — user will name a specific failure mode to include in the top tier
- Add a missing one — user will describe a pattern not yet identified
Which failure modes pose the greatest risk given both their likelihood in this specific situation and their consequence if they occur? Use H/M/L ratings for each dimension. Priority is the product — a medium-probability, high-impact failure mode outranks a high-probability, low-impact one.
Step 5: Pre-emptive Actions for the Top Three For the top 3 by probability × impact: what specific action taken now — before the failure mode activates — would reduce its probability or limit its damage?
Human Check-in
Before proceeding, use the AskUserQuestion tool. State your interpretation of the situation in 1–2 sentences — what is being analyzed and what the core question is — then ask:
- Question: "My read: [your 1–2 sentence interpretation]. How do you want to proceed?"
- Header: "Scope"
- Options:
- Full analysis — Complete all steps, reasoning shown throughout
- Key findings only — Bottom-line output, skip step-by-step detail
- Recurring failure modes only — Patterns that appear across multiple historical cases
- Reframe — The read is off; correct it and the analysis will follow the corrected framing
Proceed based on their selection. If the user reframes, incorporate the correction before running any analysis.
Output Format
Failure Mode Table
| Failure Mode | Typical Cause | Early Warning Signs | Present? | Probability | Impact | Priority |
|---|---|---|---|---|---|---|
| [mode name] | [root cause] | [observable signals] | [Y/N/partial] | [H/M/L] | [H/M/L] | [rank] |
Top 3 Failure Modes
For each of the top 3:
- Mode: [name]
- Why it's high priority here: [specific reasoning for this situation]
- Pre-emptive action: [concrete step, named owner, specific timing]
Notes
The goal is not exhaustive risk listing — a long list produces paralysis, not prevention. Identify the 2-3 failure modes most likely to be fatal to this specific endeavour and act on them now. The ones not in the top 3 are worth monitoring but not worth significant pre-emptive effort.
What's Next
After delivering this output, use AskUserQuestion to offer the next move:
- Question: "Historical failures analysed. What's next?"
- Header: "Next"
- Options:
/s4h-decision-premortem-analysis— Apply historical failure patterns to the current decision/s4h-constraint-hardness-testing— Test which historical failure causes are still hard constraints today/s4h-strategy-positioning— Position to avoid repeating historical failure modes- Done — Wrap up and synthesise what we have so far
