The Limits of AI-Assisted Risk Assessment When Stakeholder Signals Go Unrecorded
My AI workflow cut my governance and reporting workload nearly in half on a 465-application enterprise transition. It also missed the one risk that could have derailed a migration wave — because that risk never showed up as data. Here's what actually changed, and what still can't be automated.
A few months into leading a large-scale enterprise transition — 465 applications, 8 technology towers, 50+ stakeholders — I hit a moment that's stuck with me. Heading into a monthly operational review, the RAID log was updated, the KPI dashboard was current, the governance pack was ready. Everything was "on track" on paper. What actually decided how the meeting went was a 10-minute conversation
beforehand with one quietly unhappy stakeholder, before he said it in front of the room. A plan tells you what needs to happen. It never tells you why it matters or how a room full of people...
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