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AI STRATEGY

Build Guardrails and Escalation Paths

Name the Gaps Before They Hurt You

Every AI system has failure modes. Documenting and tracking these proactively helps you manage expectations, prioritize fixes, and improve reliability.

Why it's Important
  • Makes limitations explicit to internal and external stakeholders

  • Reduces risk of surprise failures

  • Enables faster triage and debugging

  • Builds a transparent culture of safety

  • Supports ethical product development

How to Implement
  • Identify recurring or high-risk failure types

  • Categorize by severity and root cause (e.g., model vs. prompt)

  • Link failure conditions to specific scenarios or user segments

  • Document known mitigations or guardrails

  • Share failure profiles with product, QA, and support teams

  • Update with each model or prompt change

Available Workshops
  • Failure Mode Brainstorm

  • Retrospective Analysis of Live Incidents

  • Root Cause Mapping

  • Mitigation Strategy Sprint

  • Public-Facing Limitations Review

  • Failure Knowledgebase Setup

Deliverables
  • Failure conditions log

  • Mitigation and workaround catalog

  • Internal wiki or knowledge base

  • Model limitation disclosure template

  • Failure-to-fix tracker

How to Measure
  • Number of known issues logged

  • % of mitigated vs. unresolved failures

  • Frequency of repeat failure types

  • Time from identification to mitigation

  • Impact of failures on user outcomes

  • Visibility of known issues across teams

Pro Tips
  • Use tags to classify failures by model, use case, and severity

  • Include failure examples in onboarding for new team members

  • Share failure patterns in OKR or roadmap planning

  • Cross-link failures to analytics and support tickets

  • Add "Known Limitations" section to public docs or UI where relevant

Get It Right
  • Treat documentation as a shared artifact, not blame log

  • Prioritize failures by real-world impact

  • Keep logs accessible and searchable

  • Regularly revisit and retire outdated entries

  • Communicate openly with users about limitations

Don't Make These Mistakes
  • Hiding or downplaying known issues

  • Failing to categorize failure root causes

  • Keeping logs in personal silos or static files

  • Treating logs as checklists instead of evolving insights

  • Ignoring recurring patterns in failures

Fractional Executives

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