Black Swans in Transformation – A One-page of Self Questions

Use this as a fast sense check. Answer yes, no, or unsure. If you have more than three no or unsure answers, latent risk is compounding.

1) Decision hygiene
– Have we written the three assumptions that would kill this decision if false, with owners and tests?
– Have we defined clear kill criteria?

2) Governance and dependencies
– Do we report on critical dependencies?
– Does each critical dependency have a single named owner who reports lag and variability, not only status?
– When an amber rolls forward month to month, do we escalate and change the plan, or do we simply note it?

3) Flow and constraints
– Have we mapped the value stream end to end and identified the constraints to production?
– Are work-in-progress limits set to match the constraints, and do we fund moving the bottleneck, not feeding the queue?
– Have constraints actually changed in the last month?

4) Scope, learning, and change control
– Are outcomes and lead indicators locked, while detailed scope remains flexible and exercised as options once evidence arrives?
– Are funding releases linked to milestones other than paperwork completeness?
– Do we measure time to first value and time from defect discovery to production fix?

5) Incentives and commercials
– Are internal teams and vendors rewarded for throughput, quality, and adoption, not bodies and documents?
– Do contracts include holdbacks tied to time to value and defect leakage?
– Do performance goals penalise long queues, rework, or slow decision turnaround?

6) Assurance and sensing
– Do we run continuous sensing, not only gate reviews?
– Do assurance teams tell you after the fact how you should have done it or are they forward looking?

7) Data and environments
– Is data quality treated as a product with an owner, backlog, and SLOs?
– Are data readiness and environment availability measured and reported like code readiness?

8) Portfolio correlation risk
– Have we run a portfolio-level pre-mortem to identify correlated failure modes across initiatives?
– Is there a live watchlist of observable precursors that we track across the portfolio?
– Do we halt or resequence work when shared constraints or shared vendors create coupling risk?

9) Reality check
– Can leaders describe what the delivery system can actually produce this month, in plain language, without slides?
– Do delivery teams agree with that description?
– When the two diverge, do we change the operating model, or do we ask for another dashboard?

Source ideas and phrasing adapted from my article, “Black swans in transformation, systemic risks hiding in plain sight.”