01
Which repeatable workflow should receive more AI authority, and what evidence would earn that authority?
Why ask: September repeatedly showed bounded agents and models preparing or executing insurance work. Why it needs an answer: Without a named workflow, owner, KPI, exception path, and stop rule, authority will expand through vendor momentum rather than controlled value.
02
What must remain human-owned in underwriting, pricing, claims, fraud, and health decisions?
Why ask: Customers, regulators, and practitioners repeatedly separated repeatable work from consequential judgment. Why it needs an answer: Unclear boundaries create conduct, fairness, accountability, and recovery risk when a model is wrong.
03
Can we reconstruct a material AI decision from source data to customer outcome?
Why ask: Provenance, model inventories, runtime controls, certification, and supervisory evaluation became recurring themes. Why it needs an answer: Weak evidence can block deployment, appeals, regulatory review, reinsurance confidence, and credit quality.
04
Are our broker and customer interfaces ready for AI-mediated distribution without surrendering advice accountability?
Why ask: Shopping assistants, conversational insurance, self-service agents, and carrier connectivity advanced across the month. Why it needs an answer: Discovery and servicing may move to external interfaces before internal transformation is visible.
05
What is our cross-line exposure if a common model, cloud, data provider, or data centre fails?
Why ask: Data-centre accumulation, cyber misuse, silent AI, model correlation, and systemic stress appeared together. Why it needs an answer: Property, cyber, liability, business interruption, supply chain, and reinsurance exposures may be one accumulation.
06
Which AI claims have a credible path to loss ratio, expense ratio, pricing, retention, or capital value?
Why ask: September included ambitious value targets, growth comparisons, capacity claims, and evidence that time savings precede decision-quality gains. Why it needs an answer: Leadership needs to distinguish source-reported ambition from realized insurance economics.
07
What architecture and jurisdiction choices are we making by selecting a model or platform?
Why ask: Insurance-trained models, in-house LLMs, sovereign deployment, headless cores, and open platforms changed the procurement question. Why it needs an answer: Model choice can determine data residency, vendor exit, portability, resilience, and system-of-record control.
08
How will we redeploy capacity released by AI while protecting judgment and customer trust?
Why ask: Farmers’ hours claim, workforce concerns, chief AI officers, and operating-model research made capacity a leadership decision. Why it needs an answer: Without training and task redesign, time savings may become service degradation, judgment loss, or unmanaged displacement.