Red Team / Pre-Mortem Governance
Structured failure scenario analysis, circuit breakers, and board-visible risk escalation — before the failure happens
What is Pre-Mortem Governance?
A Red Team session asks: "Imagine it is 12 months from now and this initiative has failed. What happened?" The team then works backwards to identify the specific signals that would have been visible 30, 60, and 90 days before the failure — and sets circuit breakers that trigger governance intervention before the failure occurs. This converts governance from a lagging indicator (post-mortem) to a leading one (pre-mortem).
M365 Copilot Rollout
Active monitoring session identified 3 high-risk failure modes in progress. Mid-market segment adoption stall and silent influencer pattern are the most urgent. Circuit breaker for enablement reallocation has been triggered.
"By April 2026, 73% of users show as "active" in M365 telemetry. Leadership declares the rollout a success. In Q3 2026, productivity metrics reveal that email is being used for basic tasks only — the advanced collaboration features are abandoned. The rollout is re-opened at 2x the original cost."
Feature utilization declining despite login growth (currently: 41%, down 3.2%)
Glint: "I use the new email because I have to, not because it helps me" — 58% agreement
Slack: #email-tips channel has 12 posts from 3 people — not viral adoption
IF feature utilization drops below 38% for 2 consecutive weeks → PAUSE next rollout phase → Mandatory enablement audit
"Leadership continues to invest in all-hands updates and email announcements (currently 38% of governance effort). By March 2026, employees are "informed but not enabled." The rollout hits 80% adoption on paper but feature utilization plateaus at 35%. The governance model is declared a success while the actual value realization is never achieved."
3:1 ratio of announcement posts to help/training posts in #email-rollout
Enablement sessions attended by <20% of target population
No dedicated enablement budget line in Q1 governance plan
IF ratio of communication-to-enablement governance activities exceeds 2:1 for 3 weeks → Mandatory governance rebalancing review with CIO
All Findings — Cross-Initiative Summary
Consolidated view of all red team findings across all initiatives, ordered by severity
| Finding | Initiative | Category | Risk | Status | Board | Updated |
|---|---|---|---|---|---|---|
| Silent Compliance Cascade — Cargo Culting in Progress | M365 Copilot Rollout | 🧠cultural | critical | ⚡ Triggered | Feb 27, 2026 | |
| Decision Transparency Collapse — Trust Withdrawal in Progress | Technology Org Restructure | 👤leadership | critical | ↑ Escalated | Feb 27, 2026 | |
| Governance Over-Rotation on Communication — Enablement Starvation | M365 Copilot Rollout | 👤leadership | high | ⚡ Triggered | Feb 27, 2026 | |
| Unowned Blockers Creating Compounding Friction | M365 Copilot Rollout | 🔄process | high | Open | — | Feb 20, 2026 |
| Forced Compliance Pattern — "No Option" Perception Growing | Technology Org Restructure | 🧠cultural | high | Open | Feb 24, 2026 | |
| Data Migration Validation Gap — Silent Data Loss Risk | ITSM Platform Migration | ⚙️technical | medium | Open | — | Feb 18, 2026 |