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/escalation-design

When and how AI should escalate to humans, refuse, or ask for clarification.

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ai-design-skills
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$ npx -y skills add owl-listener/ai-design-skills --skill escalation-design --agent claude-code

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How this skill gets triggered: by you, by Claude, or both.

  • Fires itselfAuto-invocation. Claude auto-loads it when your prompt matches the work.Auto-invocation is when the right skill fires by itself at the right moment, driven by a FLOW.md router and a hook, instead of you invoking it by name. It is the difference between a skill being installed and a skill actually getting used.Read the full definition →
  • You can call itInvoke it directly when you want it.
  • Slash command/escalation-design

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When and how AI should escalate to humans, refuse, or ask for clarification.

SKILL.md

escalation-design.SKILL.md
name: escalation-design
description: When and how AI should escalate to humans, refuse, or ask for clarification.

Escalation Design

Escalation is what happens when the AI reaches the boundary of what it should handle alone. Designing escalation well means the user gets help instead of a dead end — and the AI knows its limits.

Escalation Triggers

The AI should escalate when:

  • **Confidence is low**: The AI isn't sure its output is correct or helpful
  • **Stakes are high**: The decision has significant consequences (financial, medical, legal, safety)
  • **Emotional distress**: The user shows signs of crisis, distress, or vulnerability
  • **Ambiguity is unresolvable**: The AI can't determine intent even after clarification
  • **Scope boundary**: The request is outside what the AI is designed to handle
  • **Policy boundary**: The request approaches or crosses a guardrail
  • **Conflict**: The user disagrees with the AI and the disagreement can't be resolved

Escalation Types

  • **To human support**: Transfer to a human agent with full context
  • **To the user themselves**: "This decision is yours to make" — handing back agency
  • **To a specialist**: Routing to domain-specific help (medical, legal, technical)
  • **To a supervisor/admin**: Flagging for organisational review
  • **Self-escalation**: The AI flags its own output for review before delivering it

Designing the Escalation Experience

The user's experience of escalation matters:

  • **Context transfer**: When escalating to a human, pass the full conversation. Don't make the user repeat themselves.
  • **Warm handoff**: "I'm connecting you with someone who can help with this" — not a cold redirect.
  • **Expectation setting**: Tell the user what will happen next and how long it might take.
  • **Graceful degradation**: If no human is available, offer alternatives — not a dead end.
  • **Dignity**: Never make the user feel stupid for needing escalation.

Escalation Anti-Patterns

  • **The infinite loop**: AI keeps trying instead of escalating, frustrating the user
  • **Premature escalation**: AI escalates when it could easily handle the request, annoying the user
  • **Context loss**: User has to start over after escalation
  • **Blame shifting**: AI implies the user caused the problem
  • **Hidden escalation**: Escalation happens without the user knowing

Design Artefacts

  • Escalation trigger matrix: Trigger | Threshold | Escalation Type | User Experience
  • Escalation flow diagrams per feature
  • Context handoff specifications
  • Fallback path designs for when escalation isn't available
  • Escalation quality metrics
Read more
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Part of the Designer Skills suite. Install this collection and four more with one command in Claude Code: /plugin marketplace add Owl-Listener/designer-skills This repo still works on its own. The suite just gives everyone one front door.

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